Joe DiMaggio was an American legend—but no one hid as many cruel secrets underneath his debonair image.
1. He’s A Dark Legend
Despite his electric baseball career, Joe DiMaggio presented one painstakingly curated image to the world: That of a graceful, utterly polite gentleman. But if you scratch the surface of his life, that veneer reveals a rotten inside.
His marriage to Marilyn Monroe was infamously dysfunctional, and most don’t even know the half of it. Then there were his vicious acts of revenge, his cruel crimes, and his ultimate deathbed betrayals. Joe DiMaggio is not who you think he is.
2. His Family Didn’t Want Him
Explaining where DiMaggio got his jealousy and control issues from starts at his own beginnings. The eighth of nine children, DiMaggio’s mother desperately hoped he was the last child in their bursting-at-the-seams family, only to have Joe disappoint her when another came along.
Now, I’m not saying this is the only reason DiMaggio had a chip on his shoulder, but it certainly didn’t help. By the time he hit the big leagues, that chip was a boulder.
3. He Was Controlling
DiMaggio is inextricably connected to the New York Yankees, and became a superstar almost immediately. On the field, he was devilishly good, in the locker room he was humble and quiet—but after games, his demanding side came out.
Slim and compact, DiMaggio was always dressed impeccably, and insisted everyone in his company do the same. If they didn’t comply, he’d ice them out. He was beginning to prune his image to exactly how he wanted it. All he needed next was the girl.
4. He Had A Type
By 1937, DiMaggio was famous enough to get a minor part in the upcoming film Manhattan Merry-Go-Round. That one film put his life on a new course. While there, he met fellow bit-part actor Dorothy Arnold, a blonde beauty—and DiMaggio liked his blonde beauties. Although she was 19 and he was 23, they fell into a serious relationship, marrying two years later.
Unfortunately, domestic bliss was not in DiMaggio’s future.
5. He Was A Horrible Husband
To his adoring Yankee fans, there was nothing as American apple pie as Joe DiMaggio. So when Arnold walked down the aisle, she likely imagined a charmed life full of white picket fences, shaggy dogs, and bouncing babies ahead of her. But Arnold—and the public at large—was sorely mistaken.
DiMaggio let all pretense drop early into his marriage, and began smoking, drinking, and relentlessly cheating on his wife. That was far from all.
6. He Kept Up Appearances
If Joe DiMaggio was a bad husband (and he was) he was even a worse father. When Arnold gave birth to their son, Joe Jr, DiMaggio was apathetic at best, and mostly thought of the boy as an “irritant”. His son would later confess, “He was concerned with image, with how things looked. He wasn’t concerned with me as a person”. But DiMaggio got crueler.
7. He Constantly Abandoned His Child
DiMaggio also had no qualms about abandoning his son as an infant. Whenever Joe Jr got sick, as babies often do, DiMaggio’s response was heartless. He always made sure to decamp to a hotel to get as far from the ruckus and germs as he could. Still, not even the great DiMaggio was immune from karma, and it was coming for him.
8. He Was Cruel And Indifferent
In 1943, Dorothy Arnold had enough of what was surely one of Old Hollywood’s worst marriages, and she filed from divorce from DiMaggio. In the paperwork, she cited “cruel indifference,” which just about sums it up. If DiMaggio cared, he certainly didn’t let on to the press…but his luck wasn’t going to get any better.
9. He Retired In Shame
DiMaggio had a few more incredible years left in him at the New York Yankees—he still holds MLB records today—but it 1951, it all took a sharp downturn. His season went nowhere, and reports behind the scenes indicated he was finished. That December, DiMaggio announced his retirement, saying “I can no longer produce for my club”.
DiMaggio was now a free man in every sense. He was also about to start his most infamous years.
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10. He Met The Woman Who Would Ruin Him
In 1952, Joe DiMaggio met his downfall. The recently retired 37-year-old agreed to go on a double date with the up-and-coming, 25-year-old actress Marilyn Monroe. Like his ex-wife, Monroe was blonde and beautiful, and DiMaggio was so dumbstruck that he barely talked at all during the date. As one of Monroe’s friends put it, “You could almost hear Mr DiMaggio going to pieces”.
Yet all this had a strange effect on Monroe.
11. He Was A Bad Date
Monroe, who had grown up with a schizophrenic mother and an absent father, was in constant search of affection, even if she didn’t always get it from the right places. That said, she did get it. So when DiMaggio clammed up around her, she assumed he wasn’t interested and went from reluctant—before the date, she thought he’d be egotistical—to intrigued.
They collided in a way neither of them could ever turn back from.
12. He Had A Gross Dynamic
Whole books have been written about DiMaggio and Monroe’s dynamic, but all of them agree on one thing: It was incredibly toxic. DiMaggio was obsessed with Monroe’s beauty, and also obsessed with the way she made him look while hanging off his arm. Monroe, meanwhile, liked DiMaggio’s “paternalistic guidance,” not to mention their fiery chemistry together.
But DiMaggio’s “guidance” soon turned sour, and their chemistry erupted.
13. He Tried To Oppress Her
DiMaggio had always been a conservative, if snappy, dresser, and he began to make harsh demands of his starlet. He quite liked her curves, but considered them for his eyes only, and tried to insist she wear blouses that covered up her chest, while lowering her hemlines for good measure. But DiMaggio’s control issues spiraled further.
14. He Was Incredibly Jealous
It wasn’t just that DiMaggio wanted Monroe to ditch the Hollywood uniform; he also wanted her to ditch Hollywood all together. After all, why should the public get such easy access to his lover on screen? Monroe, to her credit, refused. As one family friend related, she wasn’t about to give up her burgeoning stardom “to make lasagna for Joe and spend her days changing diapers”.
So there were huge warning signs, but the pair went ahead and made a horrible decision anyway.
15. He Had A Hasty Wedding
In January of 1954, Joe DiMaggio and Marilyn Monroe eloped, probably making everyone who knew them palm at their faces. According to close confidants, it was what DiMaggio had been angling at from the beginning, if only because it would allow him to better control Monroe and help mould her into the wife he wanted. He started his “project” right away.
16. He Insisted On Terrifying Rules
When they married, DiMaggio set up “ground rules” for their union, most of which only served him. For one, he demanded to have final approval on any of Monroe’s upcoming films. He also wanted her to break out of her previous “dumb blonde” type-casting—which was, to be fair, a sentiment Monroe was fully behind herself.
Only, the most punishing stipulation was yet to come.
17. He Treated His Wife Like Competition
DiMaggio now believed he had a good amount of creative control over Monroe, but there was one thing he feared most of all. As one of his last rules, he told her she could never eclipse him in public. If he ever did feel slighted, he would make sure she felt it, storming off to a separate bedroom and giving her the silent treatment for days on end.
Unsurprisingly, it began unraveling almost instantly. But no one could have predicted how bad it would get.
18. He Had Bad Habits
For all that he wanted a vivacious, arm-candy wife, DiMaggio wasn’t doing a lot to hold up his end of the relationship. While Monroe was interested in psychotherapy, reading, and art, DiMaggio was interested in daytime TV, pouring himself drinks, and waiting for Monroe to come home so he could barrage her with questions about where she’d been.
And in those moments, DiMaggio was like a tiger lying in wait.
19. He Crossed A Horrific Line
Under all these strict, ridiculous rules, DiMaggio was obviously roiling with insecurity about his relative worth next to his va-va-voom wife. But this insecurity turned him into a monster. More than once, he took out his anger physically on Monroe, with his son Joe Jr witnessing some of the terrifying events. It was heading to a horrible end.
20. He Drove Her To The Brink
Under all this strain, Monroe’s reaction was heartbreaking. She was so anxious that she began self-medicating more and more with drinking. When that didn’t work, she would take copious sedatives to help calm her mind. Finally, pushed to the brink, she also struck up an affair with her voice coach, Hal Schaefer, just to get away from DiMaggio’s oppressive influence.
When DiMaggio found out, chaos reigned.
21. He Found Out Her Secret
DiMaggio was a fastidious enough man to catch onto what was happening with his wife and Schaefer, and his vengeance was cold as ice. He calmly called Schaefer up and asked him to come over—only stopping his wheedling when Monroe shouted in the background, “Don’t come here! He’ll kill you. He’ll beat you up”. Schaefer never did visit.
At first, the image-conscious DiMaggio made sure the dire reality of his marriage stayed behind closed doors. But in the end, the only person DiMaggio couldn’t truly control was himself.
22. He Couldn’t Stand Seeing Her At Work
In September of 1954, just months after their marriage and during what should have been their honeymoon phase, DiMaggio and Monroe had an infamous altercation. Monroe was shooting the now-iconic scene in The Seven-Year Itch where her dress gets blown up by the wind from subway grate.
DiMaggio, as it happened, was present and watching intently from the sidelines. And he lost his mind.
23. He Had An On-Set Freak Out
This was a provocative scene, and one DiMaggio perhaps could tell was destined for legend—both strikes against Monroe. He quickly pulled his wife into the nearby theater and reamed her out in front of her cast and crew, one of whom was the respected director Billy Wilder. For Monroe, it was the last straw, and she played the only card she could.
24. Monroe Dropped A Bombshell On Him
A month after this scene, DiMaggio got the news that broke him. Monroe had filed for divorce after only nine months of marriage, citing—very similarly to his first wife—“mental cruelty”. For perhaps the first time in his life, Joe DiMaggio had lost something he cared for, and it was all his fault. His reaction was more than a little disturbing.
25. He Got Creepy
For the next weeks, months, and years of his life, DiMaggio found increasingly creepy ways of replacing Monroe. He dated women who looked exactly like her, and soon his little black book became chock-full of blonde bombshells. At one point, there were rumors he was going to marry the Miss America winner Marilyn McKnight…who had performed a Monroe act to nab the crown.
Yet he and the real Marilyn hadn’t come to the end of their sick story.
26. He Found Ways To Keep Hold Of Her
DiMaggio and Monroe had clearly developed a toxic co-dependence, and they simply couldn’t quit. Just weeks after their divorce, he took her to the hospital for a scheduled surgery. Slipping into his paternalistic role, he then cared for her during her stay, as well as during her convalescence at home.
She, in turn, celebrated his 40th birthday alongside him with an intimate dinner. But as always, these happy times papered over dark truths.
27. She Wouldn’t Take Him Back
DiMaggio was still auditioning to be Monroe’s husband for the second time, but the starlet was well and truly done with him—at least for now. While they still slept together from time to time, she’d stopped considering him a partner, had struck up a relationship with Marlon Brando, and continued her affair with Hal Schaefer.
It drove DiMaggio to a breaking point—one unlike he’d ever reached before.
28. He Turned To A Friend For Help
Once he realized Marilyn was slipping through his fingers, DiMaggio reached disturbing new lows. One night, he was talking to crooner Frank Sinatra about his woes. Sinatra, in turn, suggested that DiMaggio hire a PI to investigate his ex-wife’s comings and goings. Yeah, great idea.
Thus began one of the most ridiculous stake outs in Hollywood history.
29. He Went To Disturbing Lengths
First, the baseball icon had Monroe’s phone bugged. Then, when Monroe moved into the Waldorf Astoria, DiMaggio took matters into his own hands and would hide out in the lobby in full cheesy disguise, a fake beard on his chin and a newspaper in front of his face. You really can’t make this up. But DiMaggio was about to go from ridiculous to unhinged.
30. He Came Up With A Dangerous Idea
One night, Sinatra and DiMaggio were out drinking again, with DiMaggio in an especially bad mood because he knew Marilyn was currently with her voice coach side piece, Hal Schaefer. That’s when the two of them came up with another “brilliant” plan. Gathering five accomplices, they headed to Schaefer’s apartment complex, intending to catch the lovers together and give them a piece of their minds—and fists.
It got very dark, very fast.
31. He Masterminded An Infamous Raid
In the end, DiMaggio’s scheme backfired brutally. When they got to the complex, Sinatra and DiMaggio busted down the wrong door, and instead stood face to face with a confused 50-year-old woman, Doris Katz, who promptly called the authorities. Despite executives trying to hush the matter up, the papers got wind and lambasted the two scorned lovers.
DiMaggio, true to his impeccable image management, always denied it. Instead, from then on, Joe tried a different tack.
32. He Changed Himself
You can’t begin a relationship expecting to change a man, but apparently you can end one. After realizing he was acting like a buffoon to get Marilyn back, DiMaggio did a complete 180. He went to anger management therapy, quit drinking, and even tried to learn more about the world outside the baseball diamond, all for Monroe’s sake.
Not that you need to feel too bad about him, but what he got back instead was gut-wrenching.
33. Monroe Sent Him An Unforgettable Message
Despite DiMaggio’s belated attempts at self-improvement, Monroe threw it back in his face. Marilyn was (rightly) reluctant to go back to him, and just two years after the split she married the playwright Arthur Miller instead. DiMaggio must have been shattered, and for years he watched the pair as man and wife. But when he saw his chance, he didn’t hesitate.
34. He Got A Tearful Phone Call
By 1961, Monroe’s marriage to Miller was in shambles—and tragically, so was Monroe’s mental health. That February, doctors diagnosed her with paranoid schizophrenia, just like her mother, and forcibly institutionalized her in New York. Lost and scared, Monroe put out a call for help…and only DiMaggio answered it. That “answer” was typical DiMaggio.
35. He Saved A Damsel In Distress
Still holding a blazing torch for Monroe, DiMaggio stormed into the hospital and demanded they release her. When the attendants initially refused, he retorted, “I’ll give you five minutes to get her out here, or I’ll tear this…place apart brick by brick”. They quickly complied, and he brought her in for medical help at a more suitable institution.
DiMaggio had nailed a situation to the wall yet again, but he couldn’t stop Marilyn unspooling.
36. He Watched Her Spiral
The next months of Marilyn’s life (and there were only months left) were agony to DiMaggio. He watched as she slipped further into drinking, substances, and mental illness. But there was a twist. DiMaggio, in tender loyalty, never blamed Monroe for this—though perhaps he blamed himself for the misery he’d caused her during their relationship.
The people he definitely did blame, however, were very powerful.
37. He Hated A Powerful Family
In 1962, Marilyn began a fling with John F Kennedy, and then with his brother Bobby. DiMaggio, jealous but also cognizant of the fast crowd the Kennedys ran in, made no secret of how much he despised them and how he felt they were dragging Marilyn down.
He even took issue with his old pal Frank Sinatra at this point, since he believed Sinatra set Marilyn up with the Kennedys for his own political gain. Tragically, all DiMaggio’s worst fears came true within weeks.
38. His Nightmare Came True
In the summer of 1962, DiMaggio received the most devastating blow of his life. Marilyn’s cold body was found in her bedroom after an overdose. Tellingly, although many sought out conspiracy theories to explain her passing, for DiMaggio there was only ever one answer: Monroe’s mental illness had finally felled her, and she’d taken her own life.
Some believe that Monroe and DiMaggio had reconciled for good or were about to reconcile just before her passing, making her end even more heartbreaking. Either way, DiMaggio acted next in a haze of grief and love.
39. He Performed One Last Act Of Devotion
In the wake of Monroe’s passing, DiMaggio intervened on her behalf one last time. He flew directly and immediately to LA to identify her body, and he organized her funeral and headstone. These were, after all, some of the last acts of devotion he could perform for her.
If there was a before and after in DiMaggio’s life, this was it. He was never the same again—or rather, all his worst qualities now swelled, tumor-like, to suffocate his soul.
40. He Betrayed His Son
Joe DiMaggio had always been an exacting man, but a new vicious streak coincided with Monroe’s spiral and downfall. Around this time, he left his son Joe Jr—who was now enrolled at Yale and having academic difficulties—out to dry, even encouraging a university official to expel him. Later, when Joe Jr experienced addiction and homelessness, DiMaggio would sneer that his son was a “bum”.
But his disregard of his family spread to more than just his son.
41. He Cut His Elderly Sister Out Of His Will
After a legendary career in baseball, DiMaggio had significant assets—but he frequently held it over the heads of even his siblings. His older sister Marie had helped out in his household, but after DiMaggio suspected she was taking gifts he had been given, he tried to cut her out of his will when she was in her 80s.
At one point, he saw his brother Dom at a hotel, and didn’t even say hello. When someone asked if he was his brother, DiMaggio replied, “So what”. As for any “friends”? Well…
42. He Dropped Friends Like Flies
DiMaggio cut old pals out of his life at the drop of a hat. In one instance, he iced devotee Barry Halper out of his inner circle just because Halper didn’t go through some largely inconsequential procedures for signing DiMaggio’s memorabilia. The friends who remained called this getting thrown “out of the phone book”—such was DiMaggio’s total commitment to pretending you never existed, even after the smallest slight.
Not that DiMaggio himself was innocent.
43. He Crowed Over A Sick Man
Vain and self-serving to a fault, Joe DiMaggio had his own horrible manners later in life. For example, he once went to the wedding of a friend’s daughter without a gift. But his most bitter act happened in front of an adoring crowd.
In 1995, on Old Timers’ Day in Yankee stadium, DiMaggio was clearly delighted when he got more applause than fellow icon Mickey Mantle—who was currently dying of cancer and could only send in a videotaped message to the fans. Yes, DiMaggio was now a hollow man. He was also a miserly one.
44. He Was Bizarrely Stingy
After growing up poor, Joe DiMaggio was a notorious penny-pincher. Later in life, he took this to shocking levels. He hated paying for anything—his car (which he only “washed” by driving out in the rain) was a Yankees’ gift, and he generally lived in apartments other people had given him. Even then, his clothes often had mildew on them…because he wouldn’t turn on the complimentary air conditioning.
In short, as the years with Monroe’s last breaths grew ever distant, DiMaggio’s grudges grew larger. His pain also grew deeper.
45. He Held Life-Long Grudges
Even in his elderly years, you knew there were three subjects you never mentioned in DiMaggio’s presence: Marilyn Monroe, Frank Sinatra, and the Kennedys. Indeed, the aging DiMaggio still held such hatred for the presidential family, he wouldn’t even go to charity events at the Kennedy Center unless he knew none of them would be there.
His worst pain, however, was hidden even deeper.
46. He Had A Sinister Tell
Whenever Joe DiMaggio was about to have a black mood, he’d display what those close to him called the “bad head,” where the sportsman would tilt his chin down. If that happened, you knew a storm was coming. And each time, you knew it had the same origin: DiMaggio was thinking of Marilyn Monroe.
Her ghost had never left him, and had turned him into a living phantom himself. Except, that is, for one thing.
47. He Kept Her Spirit Alive
What humanity Joe DiMaggio did have left was still reserved for Monroe. Although he never again visited her grave after her funeral, he did fulfill a tear-jerking promise to her. She’d always idolized how Old Hollywood star William Powell left roses on starlet Jean Harlow’s grave every week, so DiMaggio made sure to do her one better, sending fresh roses there like clockwork twice a week.
But when DiMaggio’s own end came, it was nothing short of a tragedy.
48. He Tried To Hush Up Devastating News
In the last decade of his life, DiMaggio relied heavily on his lawyer Morris Engelberg, both personally and professionally. He also forced him to keep a ruinous secret. In the late 90s, DiMaggio found out he had cancer, which he called “funny cells” to avoid the seriousness of the situation, but insisted Engelberg tell no one.
DiMaggio was trying to control the Grim Reaper just like he controlled his entourage, his bank accounts, and his public image. But this demon—like all DiMaggio’s demons—couldn’t be wrangled.
49. The Truth Came Out
Eventually, the press clued into DiMaggio’s illness, though few knew just how serious it was until it was too late. But Engelberg also eventually caved—so on March 7, 1999, the last day of DiMaggio’s life, he was surrounded by the family he hadn’t yet completely discarded or alienated. Then, before he passed, he uttered the six words that will live in infamy.
50. His Last Words Were Famous
In many ways, Joe DiMaggio’s life started when he met Marilyn Monroe, and entered purgatory when she’d died. So, almost four decades later, his thoughts were still heartbreakingly with her. As his final words, the 84-year-old man turned to Engelberg and rasped just before dying, “I’ll finally get to see Marilyn”.
Only…there’s still one thing you should know about their great “love” story.
51. He Got A Deranged Revenge On Marilyn
Joe DiMaggio was clearly obsessed with Marilyn Monroe, but few know just how dark his obsession got. In his book about their relationship, author David Heymann claims that after their divorce, DiMaggio had a $10,000 doll replica of Monroe made, which he used for the exact nefarious purposes you’re thinking of.
Going further, DiMaggio even once reportedly showed the life-sized doll off to a new lover, calling her “Marilyn the Magnificent” and boasting, “She can do anything Marilyn can do, except talk”. Ew.