Normally, wills are ways for people to divvy up their possessions after they’ve passed on. But for these people, that simply wasn’t dramatic enough. From revealing family secrets to concocting ingenious plans for revenge, not even death itself could stop these people from causing a scandal.
1. Grandpa’s Archenemy
My grandfather hated his neighbor. They lived next to each other for over 20 years. I remember well my grandfather raging at every opportunity about this guy. We never saw them speak to each other. In my Grandpa’s will, he left the guy $10k, a car, and golf clubs. Needless to say, as a family we were dumbstruck, until we found out the surprising reason why.
It turned out that they were good buddies from the army. When they coincidently bought homes next to each other they decided to play a long con on both of their families. They actually played golf together twice or three times per week and had a monthly poker game going for many years!
2. Help Thy Neighbor
My dad knows a guy that used to work with drywall. His neighbor was this old guy that lived alone. He’d go over and mow the guy’s lawn and help him out around the house in his free time. When the old man passed, he left everything to the guy, including, get this, a million dollars. My dad’s friend took the money and started his own auto body shop. He still works there today, even though he doesn’t have to, and he’s the nicest guy in the world. When he fixed my car, he refused to take any money for it.
One time, I had a young client come in to create a will before his deployment. His will was quite special; he requested to be buried in blue jeans, a Chris Jericho T-shirt, and his replica WWE championship belt. Luckily, he did not meet any misfortune on his deployment and still has time to change his will for the future.
4. King of Coffins
My cousin is a career Marine and once told me that in his will, he put that he wanted a Budweiser coffin. I thought he was joking. He was not.
5. Fly-in Uncle
I had a rich uncle. He was real crazy…and not in a good way. He would come to visit us when we were kids, maybe once every ten years. The last time that he visited, he brought us to a Denny’s. When he arrived, he met my brother at an airport, was with us for an hour, and then he got on another plane and went home. When he passed, he had no friends, and he had basically driven his wife to drink herself to the grave a few years prior. In his will, he left his entire estate to an Elvis impersonator. Everything.
6. Keeping the Good Times Alive
My dad’s friend passed, but before it happened, he opened up a bar tab with $5,000 prepaid at the horse track where he and my dad originally met. The tab was not just for my father, but for him and ten of their buddies who hung out at the track together. I thought that was pretty cool. To this day they still put drinks on his tab.
7. Coerced Confessional
My grandmother was adopted and an only child. She took care of her parents until they were gone. A week before my great-grandfather passed, the pastor from their church locked himself in the bedroom with him and had his will changed. When the will was read, it stated that my grandmother was not a person of any relation to him and nothing from the estate was to go to her.
Also, the pastor had her adoption records destroyed so that there would be no proof of a relationship. Because of this she could never find out anything about her birth family. Instead, all of his estate went to the church. My grandmother was understably a little raw about this.
8. Waiting for the Bus
When I was younger, I worked at an attorney’s office. We had a client who was a little old lady and when she passed, she gave her house and all of her belongings to a bus driver. The bus driver was nice to her and would help her out, so she felt like he deserved more than her family. We were all waiting for a riot to break out when her family found out.
9. Joke’s on You
I sat my wife down to have “the talk” because I was getting ready to deploy to Iraq. This was during the incredible sectarian dispute, and I wanted to make sure she knew everything to do in case something happened to me. She’s never serious. Ever. But I wanted her to be serious for this discussion because it was important.
I get through telling her all about it and want to know if she has questions. “Yeah, so… the life insurance. How does that work?”, she says. “I don’t really know, baby. What do you mean?” She answers, “Well, do they just put the money in there? When?” I’m sitting there thinking, “That’s weird but I know she’s not trying to be cruel. She just wants to know the logistics.”
That’s when she says, “So do they put it in my bank account? Or do they give you one of those big checks when you win the lottery?” as she holds her hands up like she’s holding a huge check. Laughter ensues. So now I have it written into the will that if I’m KIA, I want the $400K to be given to her with a gigantic lottery check.
10. Nine Lives of Luxury
My dad worked as a lawyer and he has a story that one time he had a woman leave millions of dollars to three stray cats that she had been feeding. After she passed, he had to go out and find them, catch them, put them in crates and ship them to a cat resort in Texas. It is safe to say that these cats now live a life of luxury.
11. My, That’s a Big Box You Got There
One client of mine was a guy that had a massive safety deposit box, like it was the size of a small dresser. There was a lot of tension before opening it. What could be in a safety deposit box so big? Surely something memorable! When we finally opened it, we found that it was filled entirely with coins. Several hundred thousand dollars’ worth of coins.
12. Monkey Business
My wife and I went to a lawyer to have our wills drafted. The lawyer told us about a client he had that had a great deal of money. His kids were fighting over it before he passed. Frustrated, the man decided that since he liked the monkey exhibit and the local zoo, he was just going to will all of his money and his huge estate to the zoo for the monkey exhibits. He now has a bench dedicated to his honor at one of the local zoos.
Meanwhile, his kids were ticked and tried to fight to get the money. They failed. The lesson is don’t be petty or greedy, and love your family unconditionally.
13. One Hand to Rule Them All
Growing up, my brother and I played rock, paper, scissors over every little thing. No matter the issue at hand, we would throw down our hands and play for it. My dad had a nostalgic sense of humor and he decided to put it in his will that if both he and mom passed on together, my brother and I would have to play one hand of rock, paper, scissors for everything.
14. Oh, Momma
In my office, we worked on a will that was quite demanding. The lady put in that one of her adult sons couldn’t receive his share until he checked up on his teeth and visited a dentist. If that wasn’t enough, she also stipulated that the other son must lose 70lbs. before he took his share of the inheritance.
15. Spending Eternity Together
A lady I worked for put in her will that she wanted her cats to be cremated with her when she passed. I told her that’s not going to happen, human remains and animal remains do not get cremated at once. Being the nifty cat lady that she was, she came up with a solution: she settled on being cremated separately and then joined and buried together.
16. She’s Just Being Thorough
Typically, wills are about 10 pages (for the average person). But sometimes, people push their wills to the extreme. We had a lady who had a 56-page will. She detailed EVERYTHING, from her house to the people: “wooden ladle to ____”; “toilet paper holder to ________”; “magazine basket to _________”. This woman itemized every single item in her house, no matter how useless.
17. Zoo Day!
We had a man put in his will that his family was to go to the zoo immediately after his burial —the very same day! We thought that was the most heart-warming thing a client had in their will.
18. Secret Burial
One lady told us to put it in her will that she wanted to be buried next to her husband…on her property! She lived on a small rural property. It is totally against the law to have human remains buried there. Plus her husband had passed five or six years prior. So, it’s not as though it was 50 years ago, when things like that may have been a little overlooked.
19. Can’t Borrow a Bod Like This
We had an open casket wake for my grandfather. The staff at the funeral home had put him in his nicest suit—he even had on his wedding band—but as soon as we got there, we knew something was terribly wrong. The man in the casket was not my grandfather. We were all completely furious, so we confronted the staff—but their unbelievable response only made us angrier. They put another guy in there because they had misplaced my grandpa’s body. Unbelievable.
19. Never Forget Your Disinheritance
Years ago, I worked in a retirement community. There was an older man who came out late in life and moved into the community with his gay lover. He was a Korea veteran with multiple honors and a wall of medals. He was also a bit of a jerk most days, but he had his moments and his stories were fantastic.
His children over three years never once visited him. He had a heart attack and knew he was on his way out. His children showed up but demanded his lover leave during their visits. In his will, he left everything to his lover and his lover’s one child from a former marriage. He wrote a long note about his kids’ hypocrisy of not visiting and their attitudes toward his lover. But that wasn’t all.
He left each of his two kids a pail of coal ash, to be deducted from his estate. He also had his estate pay for his lovers’ plot to be placed next to him and his wife, and in his long letter said that his kids, if they visited his grave, would be reminded of why they didn’t visit while he was alive. Frankly, it was awesome hearing his kids blow up about it.
20. Bad Education
There was a rich old aunt who was the only one in her huge family with any money, having been a doctor on the Upper East Side of Manhattan. She set up a living trust to take care of her poor relatives in the Philippines, to continue as a testamentary trust whenever she passed. Her favorite niece was in control of the trust, and of course, the niece was responsible and even-handed and never embezzled any of the money to set herself up as a newspaper publisher and concert producer and media mogul with new expensive cars and lots of first-class pan-Pacific travel, nope, not her.
Who am I kidding, of course, the trustee did all that! Hundreds of thousands of dollars were missing, and an unholy mess of sifting through money transfers and property purchases in three countries. The niece also had a bigamous marriage to some guy in the Philippines (her real husband in north America was bedridden and slowly dying), to whom she sent buckets of her aunt’s money to build a luxury villa. She vehemently denied such a relationship existed. She also had photos of the “wedding” on her Facebook page. She was not the smartest embezzler.
21. Toxic Parenting from Beyond the Grave
The weirdest will that I saw was a guy who wanted to set up a trust that stated his daughter could only receive a monthly payment if she remained below a certain (quite low!) weight. He was setting it up while he was still alive but it was a perpetual trust so that rule would stay in place after he passed. I can’t imagine having such a controlling parent that they feel the need to dictate how much I weigh from beyond the grave!
22. Next Level Tree Hugger
Where I went to college, there’s an oak tree that a man deeded to itself in his will. Now called The Tree That Owns Itself, it sits in the middle of a road, and you have to go into another lane to drive around it. The story is that a man loved the tree so much as a kid that when he passed in the 1830s, he gave the tree possession of itself. This technically wouldn’t stand up in a court of law, but the county and the local populace has accepted it and cares for it.
23. A Little Empathy Goes a Long Way
When my dad was growing up, there was this little old lady across the street without any family. She was from Finland and lost her husband during WWII. She immigrated to the USA and had no one. So my grandparents would knock on her door to chat, take her grocery shopping, etc. They also made my dad and brother help out around her house and yard. She loved my dad and uncle, treated them like her own kids and she gave them cookies and treats and presents.
When my dad was in Vietnam, she would record him voice messages on tapes and send them to him with letters telling him what life was like in the neighborhood and how she hoped he’d be home safe soon, that she prayed for him, etc. When he came home, he’d stop by to chat and help out around the house, bring her macaroons, and just sit and talk for a while.
One day she passed on, and a lawyer called my grandparents. She had left them a sizable amount of cash and stock, and her (paid off) house to my dad and his brother. My family had thought she was penniless. Never underestimate how much little, simple things can mean to people. You just might be one of the best things in their life.
24. Coming to a Family Agreement
This large French farmer’s family had been fighting each other for 15 years over their parent’s estate. Everything and anything had been utilized in this all-out conflict; debts, spoils, barns, plots, cows, wills, and whatever. Defeats followed victories, failures followed compromises, and the conflict was tearing the family apart. Eventually, someone suggested they just drag all the stuff into the farm’s courtyard, pour petrol on it, and set it all afire. Everyone agreed.
25. Hate is Stronger than a Will
My grandma’s sister was an extremely vindictive narcissist. She and her husband gained a significant number of assets over the years, including a somewhat profitable farm with over 100 acres of fields. They had a few children, all boys, and they all had wives and children of their own. Her husband passed about six years before she did.
Somehow, in their over 50 years of marriage and living on said farm, they had never bothered to go to a lawyer and write a will. Instead, she wrote a note saying that nothing was to go to her children, the wife of her son who passed almost 20 years before, or the grandchildren. She just left all her money in her safe. So, everything went into probate and the kids are still trying to figure it out. No one will say why their mom was so mad at them.
26. The Jerk
My great-grandmother and great-grandfather had a will that would give their six kids a fair share when they both passed. But my great-grandfather passed, the oldest kid went to court to get his part of the inheritance, despite the fact that clearly, he was only supposed to get it after both his parents passed. This made my great-grandmother go off the deep end.
She didn’t get to handle the sorrow of losing her husband whom she been married to for 68 years. Instead, she had to go to court many times, and then she lost the house they had built and almost everything she owned. We helped her get an apartment and tried to keep her happy, but she deteriorated quickly after those months. I hate how someone can let greed come between families. I’ve never met the jerk.
27. Knives Out
Granny was a sweet old lady, relatively healthy but had some trouble getting around and taking care of herself. Her family was the typical greedy and money-hungry scenario, only calling when they wanted something. They stuck her in a nursing home and moved far away. To everyone’s knowledge, Granny had very little money, but she still owned her property; a small house her best friend (my great aunt) took care of, and her car—a customized classic VW Bug.
The nursing home had volunteers, people to come and talk to the residents, play board games with them, basically keep them occupied. Granny’s favorite was a newer volunteer, a 19-year-old girl whom I’ll refer to as V. I only met her a handful of times, but V was a very soft-spoken and kind girl. V was the only volunteer Granny liked, because they had many things in common, one of those things being their mutual love for a specific kind of car...hint hint.
Over the next year and a half, V continued to volunteer about twice a week. Soon, Granny started to get sick, her health started to rapidly decline. Did her family come to see her? Nope. Until her last days, she only had V and my great aunt. Granny passed. Some of her family came to the funeral, but pretty much everyone only cared about the will. My great aunt said that the only ones who seemed sad at the funeral were herself, V, and a few of Granny’s old friends.
When it came time to read the will, there was a big shock. It turned out Granny had a decent amount of money stashed away—about $100,000. The family was in the dark, only my great aunt knew about it. A very small amount of that was split up and given to select family members. But the rest was divided and given to my great aunt and V. V was in complete shock. The family was mad. A few other things were given to family, select items that didn’t hold a whole lot of value. But it was about to get worse.
The car I mentioned earlier, the classic VW Bug? Granny’s teenage granddaughter had her eyes on that car since Granny was put in the nursing home! Everyone expected her to get it once Granny passed. That didn’t happen. Granny left it to V. If the family was mad about the money, they were FURIOUS about this car. Poor V cried her eyes out and said she had to leave the room. She told my great aunt, “I can’t accept it. I’m not family, that car should be yours.” And my great aunt spent over an hour and a half convincing her that Granny wanted her to have it.
Some family members followed V outside and started screaming at her, threatening to sue her, claiming it was part of a “plan” that V must have created (What? Befriend a lonely old woman and take her fortune?), telling her she didn’t deserve any of what she got, and calling her awful things. One of the calmer relatives got things settled down and my great aunt got V out of there.
It’s been a few years. My great aunt and V still talk, and V still has Granny’s bug. As far as I know, after the reading of the will was over V got a lot of nasty messages online but was otherwise fine. One of the family members did contact a lawyer but they must have told them there was nothing that could be done since V never actually got sued or anything.
28. No Horsing Around
I have a client that doesn’t communicate very well with me, though he is quite special. In my town, there was a woman who left about a million USD to her horse. Yep! My client is a horse. We work managing his investments and the sister of the deceased pulls out about 3-4% annually to care for the beneficiary of the trust.
29. Grave Games
Creating a will can be morbid. But passing on is even harder, especially for the loved ones. So, I decided to try and make the situation easier for everyone after I am gone. My will stipulates that all my assets are to go to the niece or nephew that wins a treasure hunt that will be set up! It makes me happy to think about and I thought that would be more fun for everyone involved.
30. Hunting for Candy
The client was a son who did not really talk to his father but wanted to make sure the father’s estate was wrapped up properly. They did not know if a will existed but knew that his dad had a safety deposit box. So, we get a court order to open the box, and sure enough, a will was there. However, the will left a lion’s share of his estate (maybe a few thousand dollars) to a woman no one knew.
In with the will were also pictures of a naked woman and a stage name; something like “cinnamon” or “candy,” written on the back. Soon it became obvious that the father had left part of his estate to a dancer whom he enjoyed visiting in his older age. She had no idea and they had to track her down, which was a nightmare. They finally found her and she came to the office for a check accompanied by a “male friend.”
31. Paying for a Fake Daughter
For the last 10 years, my grandmother’s brother had been paying child support and sending money to this lady whom he said was his girlfriend and the child “they had together.” For years his other children and my grandma had been trying to convince him that the girl was obviously not his. He wouldn’t budge.
The “girlfriend” would appear only on payday and stay the bare minimum. The young girl called another guy dad and even had his last name. The “girlfriend” insisted he was just her friend, but the other children found out he lived with her and all. It was obvious to everyone, except to my great-uncle who we believe was just happy for a nice-looking lady to visit him.
He paid for their whole lives, house/school/vacations. The day that he passed, she was the first one at the door. He left her and her kid $1 each, with a note saying he had given them their inheritance while he was still alive.
32. Finally Getting Payback
“To my daughter Anne, who created my beautiful granddaughter Jane, and her dear fourth husband John, who laid hands on My Jane, I leave one dollar you money-grubbing jerks. To Jane I leave all of my monetary assets, save $5,000, and my best gun which I leave to my son Bill, on the condition that he beats John bloody during the time between my funeral and my burial. Jane, bail your uncle out, please.”
Other than names, this is the exact wording of a great uncle’s will. At age nine Jane told her mother that John had inappropriately touched her and her mother told her she deserved it for being a tramp. So, the great uncle took Jane in and raised her, and his two kids got exactly what it says.
33. Let it Burn
A friend of mine is a lawyer. He had one client who, in accordance with his will, which also contained the permits to do so, had his entire estate burned while his family watched. It sounds cold, but apparently, the guy suffered and ultimately passed on from a fairly easily treatable cancer because he ran out of money and his relatives would not help.
34. Dedicated to Mr. Bobo
When I was younger, I was working as a secretary and had to leave someone’s cats to various people, which is fine, whatever. But that wasn’t all. The woman had quite a bit of money tucked away, so I also had to donate money in the cats’ names to various organizations. One of them was named Mr. Bobo. I enjoyed it thoroughly.
35. It All Happened So Quick
My maternal grandfather was wealthy. He divorced my maternal grandmother, remarried, and promptly suffered a heart attack. He was only 48 and had no will so everything went to his new wife, my mom’s stepmother. She was actually really nice and was planning on making sure that everything was “fair”…till she tragically passed in a car accident six months later.
She was a widow herself prior to marrying grandfather and had a now-orphaned a 15-year-old son from a previous marriage. He got everything. My mom and her siblings had to go to the auction at their childhood home and buy back as much of their heirlooms and memories as they could afford—and, truthfully, filched some of what they couldn’t.
36. No Parting Gift Like One Last Miff
Lawyer here. I thought I’d seen it all, but this vicious will proved me wrong: “To my wife I leave her lover and the knowledge that I was never the fool she thought me. To my son I leave the pleasure of working for a living—for 25 years, he thought the pleasure was all mine.” Best diss ever.
37. Back to Square One
My crazy mom left her house to her eldest grandson, my nephew. She also left dribs and drabs of cash to her other grandkids, the amount depending on how much she liked them; a big wad of cash to my erratic alcoholic brother; and a few thousand to me, with the caveat that if I contested my share, I got nothing.
My mom pretty much had it in for everyone. I had my own attorney evaluate the will and he said it was legally hilarious and definitely vulnerable to challenge, but it would take a lot of time and money. I ultimately said screw it and I walked away with my few thousand bucks and got on with my life. The nephew who got the house renounced the will, as he was still in college. Applying for grants and scholarships, and owning a $500k piece of property would have wrecked his fiscal profile; he also hated the house and everything about it.
My erratic alcoholic brother moved into the place, spent all mom’s money, ran up an astonishing amount of new debt using the house as collateral, and drank himself to the grave in two years flat. His equally erratic wife passed less than a year after that. Now I am executing her estate, which includes the house, on behalf of the grandchildren whom all got screwed in various ways a few years ago; the widow’s will left everything to her husband unless he passed first, which he did, and named the grandkids as a fallback.
The bonus is, as I wrap this up, I have to work with the lawyer who wrote mom’s evil, divisive will in the first place and facilitated the bit about how if I contested it, I got nothing. I suspect certain parties to this drama are going to the bad place, or they are there already.
38. On the Clock
This is the best will story I personally know. A father had a valuable antique grandfather clock, but also had two daughters so he didn’t know which to bequeath it to. His solution was that if he passed on an even day, daughter A got the clock, an odd day and daughter B got it. The daughter who did not get the clock got an equivalent cash award based on the value of the clock.
39. For my Buttercup
An ancestor of mine in the rural UK in the 1700s left his farm and everything to his nephew (no children), with his surviving wife, only getting “the second-best bed” and a provision for her to receive 3lbs. of butter per week for the rest of her life. We thought this was incredibly mean, but we wonder whether this butter was meant as an income, I mean who can eat 3lbs. of butter?!
40. All Sliced Up About It
This is going to sound weird, and unbelievable, but I have to recount this tale. The family wanted a private moment with the deceased. We allowed it, and all our staff cleared out, alongside the pastor. Within about five minutes, we hear retching, and dry heaving, and we knock, and ask if everything’s okay. But the retching doesn’t stop.
So, the staff enters the room, and by God, I’ll never forget what I saw. They were eating slices of the body – embalmed slices. God knows how toxic it was. The adults were arrested for desecration of a corpse. The children went into foster care. These were some sick people.
41. Forgive but Never Forget (or Enrich)
In her will, my vindictive grandmother left my aunt $20 as a reminder of the $20 my aunt stole from her once.
42. Tears of Joy
A woman came in after her mother’s funeral with some correspondence from the insurance company I work for. She was worried there was a bill she needed to pay and was coming to tell us that her mom had passed. She just looked SO tired, and we got to talking while I looked up the policy to close it out. She shared that in the last few years her mom had slipped into dementia and she singlehandedly took care of her. She missed her terribly, and was just run ragged.
That’s when I realized that what she had was not a health policy, it was a life insurance policy naming the daughter as the beneficiary for about $50K. I told her and she just started crying. It made me cry and I got up and hugged her and sort of just held her while she cried. She pulled away and said…”I have no idea what she left that for, everything’s been paid for.” I said, “This might be her telling you to go on that vacation and relax.” It was so touching, and she had no idea that the policy existed.
43. How Do You Like Them Manure
I once amended a will for a doctor in which he disinherited his son by removing everything he had intended to bequeath and replaced it with a “manure spreader.” I didn’t ask any questions because changing a will is an easy thing to do. But one day, that doctor will leave this earth, and his son will have essentially be told to “eat it.”
45. Creature Comfort
I had this little old lady come in who was a referral from one of our clients. He said she was a little bit strange, but nothing too odd. She had four children, and her husband had passed. She also had a couple hundred thousand dollars in various bank accounts, plus a house. So, she appointed her friend as executor and trustee, with instructions to sell her house when she dies.
A sizeable portion of her estate was to go to some weird church. The rest of her estate was to be invested and used to house her three little dogs. Those dogs are going to be much more wealthy than me in a couple of years!
46. Isn’t it Ironic?
My father in law always said his favorite story was about an old lady who was worth around 15 million and had five kids. One of her daughters married a horrible man, who would spout the foulest, most prejudiced statements he could think of. When the old lady passed, each child got 3 million—except for the wife of the foul man.
Instead, the old lady donated that daughter’s inheritance to things that her tool of a husband liked to complain about, such as historically Black colleges and universities, Planned Parenthood, the Special Olympics, her local synagogue, food banks, etc., because she felt that they ‘both deserved to be penniless and hating each other for being awful human beings.’
47. The Proof is in the Tantrum
My great-grandmother left her daughter “just one dollar and not a single penny more so help me god.” This was before I was born, but my grandmother (not the daughter with the dollar) said that when they all read the will her sister had a full-blown temper tantrum, and no one has heard from her since. I guess she had it coming.
48. No Love Lost
My father died in the fall of ‘09. The day after the funeral while singing his praises, it turns out he completely disowned my siblings and myself in his will. Imagine being three children, paraded around by your uncles, telling stories about the “good times,” to then be told that he didn’t love you and you would receive no financial support. We were devastated.
Our mother was there, as she always has been. She is our rock. At that point, that’s when my sister and I decide to completely cut off our father’s manipulative side of the family.
49. Father of Nostalgia
A client had two sons. He left a whole bunch of specific distributions to one of the sons; his truck, firearm collection, etc. To the other son, he specifically left one thing: a poster of himself in high school. I have no idea if there was some significance or sentimental value behind the poster or if it was more of a “look at what I’m giving your brother—and here’s a poster of me so you will never forget that I loved you less” situation.
50. Early Vulture Doesn’t Get the Worm
After my father’s funeral service, my mother, brother, and sister headed back to our family home. A bunch of my father’s siblings and their family were also staying at the house with us. We got home a few minutes before everyone else. I was sitting at a table in the living room when I could see their cars come down the driveway. They all got out and were hugging and seemingly congratulating each other. The reception after the service was beautifully put together and was actually a fun time. A fitting send-off for my father. So, I assumed they were still just having fun from that, until they came inside and revealed their true motives.
They all came in together very quickly, and quietly. They came up to me and my older brother sitting at the table, and kind of crowded around like a bunch of kids, about to see if they could have a cookie before dinner. My aunt Barbara smugly stood at the front and asked, “So, when are we going to be doing the reading of the will to see what was left to us all?”
My brother and I just looked at each other for a few moments before we turned to them to say, “Are you kidding? Reading of the will? Like a soap opera? There is no reading of the will. Everything that belonged to my father now just belongs to my mother!” The look of defeat, but not shame, was disgustingly transparent. They were supposed to stay another few nights. They packed up and left that afternoon.
51. A Post-Mortem Addition to the Family
I’m a lawyer who works in last wills and testaments. I was working with a nice old lady, when she drops the mic. She confessed that she had a secret daughter, and she wanted to leave the daughter some money and photographs without the rest of her family finding out. Even her husband does not know about the secret baby. That will be a fun conversation when she passes away.
52. A Little Fishy
A lady wanted to create a trust fund of £100,000 for her pet fish. When I asked if it was a special kind of fish, she confirmed that it was just a normal goldfish, but that she wanted it to be fed fresh avocado every day and be looked after by a local dog walker after she passed. She was absolutely serious.
53. Prairie Home Feminism
Several generations back, a woman (along with her brothers) in our family inherited a huge sum of money from her father (oil money in Oklahoma). At the time, women were allowed to inherit property and assets if they were single, however, all of the assets would have to be transferred to her husband if she married.
She wasn’t too happy about the situation and, in protest, never took a husband. She had a few “friends” over the course of her life and lived a very comfortable life until dying of old age. At which time, her estate was divided amongst all of the female descendants in the family.
54. Till Death Do Us Part… Or Not
When my best friend died, he wanted to have an alternative funeral. We were just trying to honor his memory, but in an instant, it all went so horribly wrong. We figured that he would have liked a “sky burial” of sorts. So at the height of the funeral party, we released his ashes into heavens with a giant balloon. After a few meters of flight, the string snapped and his remains rained down and covered the mourning crowd.
Everyone made their best efforts to get very drunk as soon as possible. No one there will ever speak of this again.
55. Some Things Are Worse Than Nothing
When my friend was 18, his dad wrote him out of the will before suddenly passing away. The strange thing was that they always got along. It seemed very suspicious. He was then kicked out of the house by his father’s evil wife without a penny to his name. On Christmas Eve, the client went back to get some photos he left there and saw something he shouldn’t have. It was then that he learned just how evil she really was.
He knew where she kept the spare key, so he let himself in. On the way to his room, he saw the step-mom’s phone sitting on a table and as he passed by she got a text message. It read something like, “I’m so happy we got away with it and we can finally be together. He didn’t deserve it anyway.” My friend was convinced that she forced his dad to take him out of the will, then somehow machined his dad’s death with a secret lover. He’s in law school now and is planning to go into estate law to help people get through problems like the one he had.
56. 100 Pennies in the Wind
My great-grandmother left her daughter “just one dollar and not a single penny more, so help me God.” This was before I was born, but my grandmother (not the daughter with the dollar) said that when they all read the will, her sister had a full-blown temper tantrum, and no one has heard from her since. I guess she had it coming.
57. Dress to Impress
My grandfather left me a navy blue tie with pink elephants. It looked ridiculous, but my grandmother said that he wore it to intimidate people in business. He thought that someone willing to wear such a ridiculous tie projected the idea that he didn’t care about what people thought, and that scares people. He wanted me to have it so I could do the same.
58. The Mistress
I received a phone call from my late husband’s girlfriend the day of his funeral. She was phoning his cell phone which I had turned off while he was in the hospital. She told me that my husband had been paying her rent for the last year. The bank had recently foreclosed on our house. I had no idea he was unfaithful to me, but she knew all about me.
59. Black Humor
At my dad’s funeral, one young cousin said, “I wish we could take Grandpa home.” My son’s response was utterly disturbing. He just said super matter-of-factly, “We can’t. He’s going to start stinking in a little bit.”
60. Baa Baa Black Sheep
One client left a specific gift of $10K to one son, and left him out of the much-more-valuable estate as a way to punish bad behavior. However, by the time he passed, our client had a serious reversal of fortune. His estate was worth about $10K, so he effectively disinherited the “good” children and left the black sheep everything.
The bad kid appeared to be very poor, compared to the others, and the look of grateful surprise on the poor kid’s face was almost as priceless as the shock on the others who thought they were getting rich.
61. Taxi Driver
One of our clients passed recently. Turns out the man she left almost everything to, including the residue of her estate—which was considerable—was her regular taxi driver. She had also named him as her executor. He had no clue. The person who had been named as her executor and main beneficiary on her previous two wills, a close friend of many years, was understandably flabbergasted and contested the will. We informed Mr. Taxi Driver, who didn’t even know our client had passed, and the will was upheld.
62. First to Go, First to Settle the Dispute
I worked with trusts and estates for many years. One of my favorite clients was a widower whose wife had passed 20 years earlier. After his wife’s passing, he wanted to travel the country in a motor home but was too grieved to do so. Years later his old army buddy’s wife passed and they re-established their friendship during their retirement years. He finally bought the motor home he’d dreamed of and left with his buddy to travel the continent, which they did for many years.
After he passed, he left a new motor home to his buddy, but with one stipulation. The buddy had to mount a set of 6-foot longhorns on the hood of the rig before it could be his. It sounded like a Texan vs non-Texan dispute they’d had for many years. Absolutely brilliant, and seemed like an amazing friendship. I would have loved to hear their traveling adventures over the years.
63. Tell us What you Really Think!
My grandfather left my uncle three things from his rather valuable estate: one dollar in unrolled pennies; a framed copy of the contract my uncle signed saying he owed my grandfather $100 000, which he had never repaid; a framed copy of the letter my uncle sent my grandfather saying he was disowning my grandfather for “being cheap.” I was only a kid, but I understood that my uncle was getting shaded from beyond the grave.
64. That Thing You Get
I was a courier in Seattle and filed the will of the guy who owned the Space Needle. Yes, it’s private property. There was all this interesting stuff about how the Space Needle would be administered, but what I really was interested in was that he owned a HUGE collection of Volkswagens, most of them the Volkswagen Thing.
For those who don’t know, the Thing is a sort of boxy-looking Volkswagen bug. There were, I remember, 43 of these vehicles, all in their different conditions. Each of the children and grandchildren were getting a Volkswagen (and a few other older kitschy Volkswagens, like Beetles and some vans) that represented how much their grandfather had liked them.
65. Purr-fect Lifestyle
One client left $100,000 to his two cats so that they could “maintain their current lifestyle.”
66. Clowning Around
Knowing how status-conscious her greedy relatives were, one lady decided that she would make them suffer for it. When she finally passed, her lawyer approached the family with instructions for her final wishes. According to the will, the only way the relatives could get the money is if they followed the funeral instructions to the letter.
I don’t remember all of the absurd details in her instructions, but the central theme is pretty unforgettable. She required an open-casket funeral, with all family members in attendance—and demanded that her body be dressed up like Bozo the Clown, including makeup, red nose, crazy hair, massive shoes, the works.
The family tried to protest, but the will was extremely clear. They either attended the Bozo the Clown funeral, or they didn’t get a dime. So they did it. These stuck up vultures had to stand there for hours, glowering, taking weird looks from all of their friends & neighbors as people got close to the casket and realized the deceased was dressed like a clown!
According a funeral parlor employee, the best part of the service came when they tried to shut the casket… and couldn’t, because the massive shoes got in the way. They had to bend these 24-inch shoes in half to get the lid closed.
67. Munificent Motivator
Client: “I’d like to leave $100,000 to my son, $100,000 to my daughter, and $10,000 to each of my ten nephews.” Lawyer: “But sir, your estate is worth about $500. Where are your heirs supposed to get this money from?” Slamming his cane on floor, the client roared, “EARN IT, JUST LIKE I HAD TO!!”
68. Post-Mortem Helicopter Parenting
A woman had fallen out with her daughter because she hated the husband that the daughter had chosen. This feud went on for years, to the point where they never had any contact, because whenever they did, things would just get pretty ugly. The daughter refused to leave the husband, and the mother demanded that she did.
So, when the time came to read the will, the daughter was surprised to learn that her mother had left her a good portion of money. However, there was one stipulation: she got the money on the sole condition that the daughter change her surname and her children’s surname back to her maiden name, effectively removing this hated husband’s name from their family tree.
By the sounds of it, this was a real sticking point for the daughter and the solicitors were pretty confident that the daughter was going to forsake her inheritance, which was a pretty large one, in order to keep her husband’s name.
69. It’s All About Timing
My great-great-grandfather left all his money to the eldest child of his eldest grandson and arranged for it to be delivered 50 years after the last of his relatives alive at the time of his passing themselves passed on. Lucky me, I’m that descendant, but my grandmother was born right before he had passed, and she’s probably going to live another 20 years, so if I make it to 90, I’ll be filthy rich. Or my kids will have a nice retirement, I guess. Anyway, I always thought that was about as vindictive as you can get.
70. Booby Trap
I was forced to write a will due to the health insurance I get at work and, amongst the sensible stuff, the in-house lawyer said it was totally okay for me to add this clause: “My funeral wishes are that I be buried in a coffin which has been spring-loaded, such that opening the coffin would cause alarm to future archaeologists.”
71. Never Change
My grandfather’s will had several conditions for our inheritance. Some were heartwarming, but most were strange to fully absurd. For example, my parents both had to remain left-handed. The only thing I received (or really cared about) was a 1932 Philco radio (it was the first radio I restored when I was a kid). To get it, I was required to promise that I’d keep “the old beast,” as he called it, running for as long as I owned it.
My daughter received a music box on the grounds she remains the eldest great-granddaughter (?). She also received a couple of puzzles that she had helped my grandpa with when we had visited a few times before his passing, again on the grounds that she actually “finished the darn things because he had never gotten around to it.” Actual wording from the will!
Leave it to my grandfather to give us a reason to laugh after leaving us!
72. Surfacing Secrets
A client of mine confessed to me that she has a secret daughter. She wanted to leave the daughter some money and photographs without the rest of her family finding out, because nobody knows about her. Even her husband does not know. That will be a fun conversation when she passes away and the will is read!
73. Better than Weight Watchers
One client set it up so that his will could be awarded in financial installments to his daughter. The only catch? His daughter had to remain under a certain weight. I was flabbergasted. It didn’t even make sense, because she was not and had never been overweight! Dude was controlling her diet from beyond the grave.
74. Spit Happens
My great aunt had about $2 million when she passed; she left half to a small church in the middle of nowhere and the other half to a llama sanctuary. She left each of her family members about $25. She had no children of her own, and most of the extended family was greedily making plans for how they’d spend her money. It was her final revenge against them. I was about 9 at the time, and was thrilled at the $25 I got.
75. The Car Collection of Oz
My grandfather was a Vietnam veteran who suffered from PTSD. It got worse in his later years and he would often isolate himself from the rest of the family, often hiding out in his bedroom when visitors were over. My grandmother would often tell us stories about how he had inherited a significant amount of money from his father way back when. She said that in their younger years he spent the money on luxurious dates and trips. After returning from Vietnam, he spent the rest on the house where he and my grandmother raised their children.
A couple of months before he passed, we found out that he had written a will. Even my grandmother didn’t know about it. We all assumed that he wouldn’t have much to leave since most of the money he had saved was being used to take care of him because he had been placed in a care facility as his PTSD worsened.
His will told of a warehouse in Township, Michigan that held a large collection of vintage cars. He said that the warehouse was passed down from his father, and he had all the documents to prove that he was the owner of some type of warehouse. His will estimated that the cars be worth an excess of two million dollars in total. The money from his collection would be split between his four children.
We had no idea this collection ever existed. It just made no sense. My father and his three brothers had all grown up in Plano, Texas. None of us had ever been to Michigan before. Even our mother couldn’t recall a time of our father ever having even gone to visit Michigan. After a long debate, my father and I, the only ones who could manage to find some time off from work, agreed to fly out to Michigan to see this collection first hand.
After a few thousand dollars spent on plane tickets, hotels, etc. we finally arrived at the warehouse my grandfather owned. It was a rundown warehouse, but it was tucked away within a compound of other warehouses that seemed to be otherwise well taken care of. Finally, code in hand, my father punched the numbers into the keypad and the giant door began to rise.
What was inside is beyond words. There was absolutely nothing. There were a few homeless people that managed to sneak in through a hole in the corrugated metal around back, but there certainly was no car collection. We were able to contact a few owners of the neighboring warehouses and to their knowledge, no one and nothing had ever been inside of those warehouses in the years they had been there.
To this day we don’t know what happened. We all just assume that the PTSD caused him to create some kind of fantasy in his mind. That maybe he purchased the warehouse believing it was a safe house for him if he ever needed to get out of Plano.
76. Favoritism at its Worst
I worked on a will from 1986 that included the craziest provision I have ever seen. It stipulated which of the woman’s three sons was allowed to name one of their children after her. Apparently her name had been “in the family for time eternal,” and she wanted to make sure the best son got to carry it on. Oh, and her will also included a lengthy explanation for why the other two kids weren’t good enough.
77. No Time Like Death to Start Living
My husband’s relative died, and there was a gathering at her house after the wake. These two people walked in, and while they seemed odd, I didn’t think much of it—but they were about to ruin the entire day. I didn’t see them for a while, but then I went into the garage to get some drinks and found them leaning against a car and engaging in some pretty vigorous intimate relations. It was absolutely horrifying that they would be so disrespectful—and that I had to be the one to see it. I wish the story ended there, but things were about to take a dark turn.
Another family member who was standing in the kitchen saw what I saw, and I guess she told the widower. The next thing I know there is shouting from the garage and the widower is telling these two people in no uncertain terms that they needed to leave. Apparently, not only were they having sex in the garage, but they were doing lines of coke off the hood of the car. Only a few people who were at the gathering found out what happened, thank goodness.
78. Better Safe Than Leaving Your Kids in Security
My mom put in her will that if she dies under suspicious circumstances that my sister and I won’t be left anything. She watches a lot of true crime.
79. Shout Out
My grandfather has a rather unique will. It directs the lawyer to say, “hi so-n-so,” to several people, just so he can say that he mentioned that person in his will. He tells lots of people in the family that they are “in his will.” It’s a joke that only he thinks is funny, and he won’t be around for the punchline. I think it’s brilliant. He has about 10 people mentioned.
80. Benevolent Beggar
I had a guy be extremely charitable when we were drafting his will. He left a million to his church, two million to a local hospital, and another two million to the American Heart Association. Then we gave him a quote on how much it cost to draft the will, and it wasn’t much, because it was a rather straight-forward document.
He asked for a payment plan; he couldn’t afford the will. The dude had no money! He thought you could just leave money to people or organizations, and that the government would foot the bill. He got really mad when we told him that wasn’t how it worked.
81. Everything is Better With Bacon
A co-worker of mine has it in his will that before he is cremated, he wants to be wrapped in bacon. He has no family and a lot of money and this dude really loves bacon. He said it’s going to cost somewhere between $2,000 and $2,500 to be cremated in bacon, but it’s totally worth it to him.
82. Great Ride
I did a few pro bono wills. This big guy asked me to give everything back to the community because he had no living immediate family. No problem. Then he told me his one exception: his Vietnam-era motorcycle. He said it was the first thing he bought after getting home from service, and he wanted to be buried with it, literally on it and in a riding position. I helped him set aside the funds necessary to do it. Dude was awesome!
83. It’s All in the Cards
My law professor told me about a client who left his three sons and grandsons his extensive baseball card collection. It seemed normal when my professor first heard of it; but then, he was handed a handwritten chart that had several hundred cards listed in one column, with the name of the recipient and why that person was getting the card in two more columns. “I leave this pitcher to Bobby because Bobby can’t throw.”
84. Famous Last Words
When my father died after a long and painful battle with cancer, a pastor at my mom’s church spoke at the funeral. The entire time that she was talking, I wanted to walk up there and punch her in the face. She had the audacity to stand in front of us and speak about how devastating cancer is. If she realized that I knew the chilling secret of her past life, she would never have had the guts to show her face.
That pastor used to attend a different church, but had to leave after she was caught for having faked cancer for two years. Her husband left her and her daughter disowned her after they found out. My mom was the secretary at that church. So she knew, and had already told me. My dad’s funeral was only like two years after that whole thing went down. I would have walked up to the podium and punched her right in the face were it not disrespectful to my parents.
85. To Beyond the Grave
I advised on a will where the deceased had left considerable assets to people who had already kicked the bucket by the time the will was read. There is nothing unusual in that per se, except that these individuals were long dead when the will was made. The lawyer apparently asked the guy, “You know you’re giving your money to dead people?” and even sent him to a doctor to make sure his mental state was okay. The doctor gave him a full bill of health and said he was perfectly compos mentis, so the will stood.
86. Meticulous Planning
I had a client who insisted I write this in her will: “To my daughter Anne, who created my beautiful granddaughter Jane, and her dear fourth husband John, who laid hands on my Jane, I leave one dollar, you money-grubbing hooligans. To Jane, I leave all of my monetary assets, save $5,000, and my best firearm, which I leave to my son Bill, on the condition that he confronts John with it during the time between my funeral and my burial. Jane, bail your uncle out of jail, please.”
87. Psycho Granny, Qu’Est-Ce-Que C’est?
Not quite a will, but too good not to share: When I was about 31 years old, I found out my maternal grandmother, who practically raised me, killed my grandfather. I was doing research trying to build out a family tree and wanted to find out about my grandfather who died about four years before I was born. We never really talked about him or how he died. I found an article about his death in 1978 and had found a corresponding police report number for an arrest of my grandmother in the same year.
I didn’t immediately put the two together, but once I did, I put in a FOIA request for the case file. Apparently, my grandfather was in ill health, had a few strokes and needed A LOT of assistance; assistance my grandmother grew tired of. One day, he was sitting in his chair and she just snapped and stabbed him numerous times, killing him.
She was arrested, tried, and eventually found not guilty by reason of insanity. She spent some time in an institution, only to be let out in 1981, the year before I was born, to move in with my family. As she lived in our home, she basically raised me from a child. She was the sweetest lady in the world and this SHOOK me.
When I asked my dad if it was true and how he could let her alone in our home with me as a child, his response was, “Oh, you didn’t know that? Well, you turned out alright.”
88. Reverse Golden Rule?
My father has been heavily involved in my great aunt and uncle’s lives since their health began to decline. They are both in their mid 90’s with no children, and my father has seen their will. They have a small fortune in excess of $1,000,000—and have left it all to a local dog’s home. When my dad asked them about it, my great uncle’s response was “nobody has helped me in life, so I won’t be helping anybody either.”
We had an 84-year-old client who was, in the simplest terms, quite insane. She would call every single month to change her will. It would always be small details, such as removing her daughters because they hadn’t called her in a while, or increasing one child’s percentage and lowering another’s based on whether she was mad at them or not.
But there was one part that she would never change: what she would leave for her dog. She wanted to leave her dog $25,000, plus more money for the care of the dog and to make sure she lived comfortably. Sadly, her dog passed away before her and she had to remove that part from her will. So, she just went back to playing with the percentages that her daughters would receive.
90. The Golden Rule
A good friend of mine looked after an older lady. She was his neighbor and, as far as he knew, she had no family. So, he was at her place every day when he wasn’t working. I met her a few times, she was a sweet old lady. She had three cats that were her babies, she spoiled them to no end. She even had a “cat room” for them.
Well, one day after my friend had been looking after her for a few years, she passed peacefully in her sleep. He found out that she named him in her will. He attended the reading and found three 20-something ladies there too. Turns out the lady had moved across the country unannounced a few years earlier, and had disappeared from the daughters’ lives.
The old woman left my buddy 19. Million. Dollars. She left the cats to a lifelong friend from her home state and donated all of her belongings to the Salvation Army. And her daughters? Each received, “A single litter box and all of its contents,” along with one $20 bill each to “give them each a last taste of all she was to them.” That sweet old lady is my hero.
91. Scrupulous Script
My grandpa left me all his tools, a pretty good chunk of change, and his dog Tanner. But, to get it I had to do some…strange things. According to the fine print in his will, I have to make sure his live-in girlfriend at the time got nothing at all, and tell my uncle that he was fat and his wife was going to leave him if he got any fatter. There was literally a script inside the will.
92. The Ally
After my nana’s death, I found out that her marriage to my papa was a complete lie. It turns out that she only married my papa and had three kids with him all as a cover story for him being gay. This was during a time of LGBT violence in America. The kicker is, they really pulled off the married couple routine and I think they were genuinely compatible and happy together.
A regular customer at the store I worked in told me he was terminally ill, which upset me because I’d gotten to know him well. He was a good guy, and it turned out that he had quite a bit of money. He had a daughter with whom he was not on good terms. He told me that he was leaving her “the contents of his bank safety deposit box.” It sounded nice, but there was a huge catch. Inside, he left a bunch of pop-up snakes, primed and ready to burst out when the box was opened. Then the rest of his estate was to be used to fund the building of a respite home.
94. A Twist in the Funeral Plot
The mother of the deceased came to the funeral out-of-her-mind intoxicated. She put on an over-the-top show of crying and screaming about how much she loved her daughter—but soon after, the dark truth came out. It wasn’t long after that terrible day that she was convicted of her daughter’s murder. Her performance didn’t fool anybody, and I hope she rots in jail for the rest of her life.
95. Spoiler Alert Will
Two sons of a really wealthy couple go to the family lawyer to have their recently deceased parents’ will read. The lawyer is super nervous because he has known them both since they were kids. One son gets the entire inheritance, and the other gets nothing. The explanation was that it should be passed through to blood relatives only. So that was the day he found out he was adopted.
96. A Shocking Turn of Events
The strangest, and most embarrassing, will reading was in a room crowded with relatives when a man who passed fairly young left absolutely everything to his 26-year-old stepdaughter, which was quite a lot of money and property. The two ex-wives and his children from the first marriage got nothing, nor did siblings, nieces, nephews, etc. The will specified that a DVD be played to explain why the stepdaughter was getting everything. Like everyone else, I thought it’d be the guy explaining the big “screw you” to the rest of the family.
What followed was completely unexpected. It was a hidden camera recording of the guy and his stepdaughter going wild in bed together. The video started in mid-action, with her screaming “yes oh god yes!” It had obviously been edited to start with maximum shock value, and it worked, because it took about 30 seconds for me to recover enough to turn the thing off. It was definitely the biggest “holy moly” moment of my career.
I later learned that the guy and his stepdaughter had a relationship since she was a teen, all the way to when he passed (when she was 26). Apparently, though this is second-hand and I can’t confirm, there were multiple clips of various video bits through the ages on the DVD. At the end of the DVD, the guy explains that the stepdaughter gets everything because she’d been “the best lay of his life.”
The worst part was that the will specified that I was to give every single family member their own copy of the DVD. The copies had been kept in a box and had been distributed prior to the showing, so everyone had “The Best Moments Of” in their hands, at the time the DVD was playing.
Epilogue: the family sued and lost, believe it or not. The girl got to keep everything.