Behind Tommy Dorsey's Sweet Smile
Wildly popular musician and bandleader Tommy Dorsey became known in the 1930s as the "Sentimental Gentleman of Swing". Well, his wives and bandmates may not agree about the "gentleman" part. The fact is, Tommy had a temper, and it made his marriages tumultuous and working with him a downright nightmare. But this was only the tip of the iceberg.
Pictorial Parade, Getty Images
1. He Was A Coalminer’s Son
Tommy Dorsey was born in Mahoney Plane, Pennsylvania, on November 19, 1905. His father, Thomas Francis Dorsey Sr, had left the rough life of working in the mines to become a marching bandleader. Thomas was sure about one thing: no son of his would end up working in the mines.
He’d do anything to keep his children far and away from that horrible job.
2. He Had A Tough Childhood
Tommy's father was reportedly hard on him and his brother Jimmy. Not only did he want them to learn all brass and woodwind instruments, but he also expected perfection. As it turned out, Tommy and Jimmy would later deal with their father’s aggression in two very different ways.
Michael Ochs Archives, Getty Images
3. He Got His First Gig
Tommy’s brother, Jimmy, was already performing by the age of nine. When Tommy turned 15, his brother got him a job with the Scranton Sirens. The brothers performed and traveled with the Scranton Sirens, and other bands that had leaders like Rudy Vallee and Vincent Lopez.
People were starting to notice these incredibly talented brothers.
Maurice Seymour studio, Wikimedia Commons
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4. They Had A Hit
Decca Records signed up the Dorsey Brothers in 1934. Their first hit song was “I Believe in Miracles”. Part of the Dorsey Brothers Orchestra was rising star Glenn Miller. Miller helped the brothers out by composing hit songs like “Tomorrow’s Another Day” and “Harlem Chapel Chimes”.
But these brothers were actually very different.
Unknown authorUnknown author, Wikimedia Commons
5. He Was The Business
As it turned out, there was a big difference between Tommy and Jimmy Dorsey. Tommy was much more savvy in the business end of music. He quickly established himself as the “set-up man”. This meant he made extra cash setting up musicians he knew together and sending them out on gigs.
But setting himself up as a sort of boss would have some very negative consequences.
William P. Gottlieb, Wikimedia Commons
6. He Lived With Overwhelming Stress
Tommy’s personal life had taken an odd turn very early in his life. He married Mildred “Toots” Kraft when he was just 17 years old. When the depression kicked in, he was already a father of two. Being such a young father added stress to Tommy's life, and he dealt with it by hitting the bottle. Compared to his brother, Tommy was suffering. And to make matters worse? His temper was also getting in his way.
Michael Ochs Archives, Getty Images
7. He Didn’t Get Bing
Through an agency, the Dorsey Brothers acquired a singer. This was Bing Crosby’s younger—and far less famous—brother Bob. When Crosby joined the band, Tommy just let him sit on the sidelines. He didn’t introduce him, and he didn't hand over a microphone. After a few days of this, Tommy clearly explained the situation, and he didn’t hold back.
CBS Television, Wikimedia Commons
8. He Told Him The Truth
Tommy took Bob Crosby aside and explained that his orchestra was the best in the world, so of course, it deserved to have the best of the Crosbys. Since that wasn’t happening, Tommy basically said that Crosby was on his own. From the horrible interaction, Crosby got a "nervous vibrato” to his voice that he never recovered from. You could say that Tommy tainted his career, and this wouldn't be the only one.
But he also had anger to dole out to his big brother.
Michael Ochs Archives, Getty Images
9. He Called Him Out
It wasn’t something typical—like a fight over a woman—that caused a rift between the brothers. Something about music sparked the conflict between Tommy and Jimmy. They disagreed about what tempo they should play. Sometimes, Jimmy would call out to Tommy in the middle of performing a song. He’d call the tempo “wrong”.
Of course, this made Tommy mad.
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10. They Fought On Stage
One concertgoer remembers a particularly heated exchange on stage. He said that the brothers basically had a boxing match over the tempo of a song. This happened right in front of the audience. They didn't care who saw their lack of brotherly love. This feud between Tommy and his brother was about to come to a head.
11. He Was Too Fast
It was May 1935, at the Glen Island Casino in New Rochelle, New York, when this feud of the tempo came to its tragic conclusion. The song was “I’ll Never Say 'Never Again,'" and Jimmy loudly complained that Tommy had started it too fast. That's when something inside Tommy snapped—and he didn't hold his temper in check.
12. He Ended The Band
With his brother’s complaint still ringing in his ears, Tommy turned to him in front of the entire audience. He then said the most tragic words imaginable: “You want the band? It’s all yours”. Then he stormed off the stage. And with that, Tommy put an end to the Dorsey Brothers. But there was just one problem.
Michael Ochs Archives, Getty Images
13. He Had To Return
The thing was, though Tommy had made a dramatic exit, the Dorsey Brothers had made multiple bookings as The Dorsey Brothers’ Orchestra. Music lovers had already paid good money to see them, so the boys had to deliver. Tommy reluctantly agreed to finish their bookings. But when they’d played every gig, he was still set on his original decision: he wanted to walk away.
Tommy was through with working with his brother.
14. He Was Ready For Something New
Upon their separation, Jimmy headed to California to be a part of the Bing Crosby Kraft Music Hall program. All Tommy had to do was form a new band. Instead of doing that, he just took over an existing one. He changed the Joe Haymes band into Tommy Dorsey and his Orchestra and hired trumpeters Pee Wee Erwin and Zeke Zarchy. He also added a female vocalist named Edythe Wright.
Tommy was ready to take on the music world.
15. He Had A Friend In Need
Tommy Dorsey had a hit record with “Marie” and was getting quite comfortable financially. His old pal Glenn Miller was suffering a little, so he offered to lend him some cash to start a new band. Tommy was so kind, he didn’t even want Miller to pay him back. He just wanted a percentage once Miller’s new band started making money.
But things tend to go wrong when friends loan money to friends. Especially when the lender is Tommy Dorsey.
Donaldson Collection, Getty Images
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16. He Doled Out Punishment
Even though Tommy didn’t ask for repayment, Miller decided it was best to keep his finances tied up in an unproblematic bow. He repaid Tommy the $5,000, and that should have been that. Somehow, Miller’s behavior angered Tommy. Maybe he'd been hoping for a better payout with a percentage of the band. Whatever the reason, Tommy now had vengeance on his mind.
17. He Tried To Destroy Him
In order to punish Miller, Tommy came up with a chilling plan. He invested in an unknown band and put it in direct competition with Miller’s band. The idea was to run Miller out of the music industry. Because of Miller’s huge talent as an arranger, this evil scheme went nowhere.
But when it came to making trouble, Tommy was just getting started.
18. He Went Behind Her Back
Not only did Tommy fail to destroy Miller’s career, but it looked like Miller’s band would outdo his band. With this kind of stress, Tommy became more and more difficult to work with. It didn’t help matters that Tommy had fallen into bed with his orchestra singer, Edythe Wright. Of course, this was behind his wife’s back—and unsurprisingly, this infidelity caught up to him in the worst way.
Mergentroid, Wikimedia Commons
19. He Got Caught
Tommy dealt his wife Mildred an awful betrayal by cheating on her, and sadly, this went on for quite a long time. However, the truth had to come out eventually. When she eventually learned about the other woman, she gave him an earth-shattering ultimatum. He had to choose one of them; he could not have both.
Tommy's response had startling repercussions.
![Gottlieb, William P., 1917-, photographer.
[Portrait of Tommy Dorsey, WMCA, New York, N.Y., ca. Oct. 1947]
1 negative : b&w ; 2 1/4 x 2 1/4 in.
Notes:
Gottlieb Collection Assignment No. 113
Reference print available in Music Division, Library of Congres](https://www.factinate.com/storage/app/media/factinate/2026/6/10/178106119260615754e5894d8d93e0c9aaa19fc1711fbb55a5.jpg)
The Library of Congress, Wikimedia Commons
20. He Dropped His Mistress
Tommy didn't need to be told twice. Once Mildred threatened to walk away from their marriage, he had no trouble making up his mind. He left his mistress, Edythe, in the dust, who had no choice but to exit her role in the orchestra. Sources suggest that this negatively impacted her career, as she slowly disappeared into obscurity.
But despite Tommy's attempt to salvage his marriage, the damage couldn't be undone: he and Mildred divorced in 1943. But his woes weren't over yet. There was still trouble lurking on the horizon.
21. He Was Ruthless
It seemed like Tommy had a great talent for stirring up drama. When he heard a rumor that his singer, Jack Leonard, wanted to leave the band, he reacted in a brutal way. There was a heated confrontation, a denial of any wrongdoing, and then, finally, there was a vicious firing.
Tommy’s temper was out of control—and it had the potential to break up the band.
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22. His Temper Was Notorious
Tommy's temper was his worst enemy, alienating some of the members of his orchestra. But it was the excessive name-calling that angered Max Kaminsky, Bud Freeman, and Dave Tough. They eventually all quit the orchestra. When he asked them to stay, they complained about bad pay and being under constant attack.
Tommy's response was unbelievable.
![Gottlieb, William P., 1917-, photographer.
[Portrait of Max Kaminsky, Eddie Condon's, New York, N.Y., ca. Sept. 1946]
1 negative : b&w ; 2 1/4 x 2 1/4 in.
Caption from Down Beat: Galloped back to Condon's to pick up dictaphone rolls and interrogate Max K](https://www.factinate.com/storage/app/media/factinate/2026/6/10/178106143357de5a11d75c1cc35c8d3f0c64237301b0804072.jpg)
The Library of Congress, Wikimedia Commons
23. He Was Arrogant
Even with band members leaving, Tommy Dorsey couldn’t find it in himself to be kind. He cruelly said that one of the perks of being in his band was that the musicians got free music lessons “just listening to me play”. Even with this amount of arrogance, Tommy knew he had to make a change.
Michael Ochs Archives, Getty Images
24. He Changed It Up
In the music scene, Tommy Dorsey’s talented rival, Glenn Miller, was busy gaining popularity. Tommy knew he had to somehow compete and find an arranger as good as Miller. His solution? Strategically luring Sy Oliver away from another band. But that wasn't all. Around this time, he also came across an unknown singer named Frank Sinatra.
This was about to get very interesting.
![Gottlieb, William P., 1917-, photographer.
[Portrait of Sy Oliver, New York, N.Y., ca. Sept. 1946]
1 negative : b&w ; 2 1/4 x 2 1/4 in.
Caption from Down Beat: Sy Oliver has returned to the airlanes over the Mutual network on Friday nights (8:30 to 9 EDT](https://www.factinate.com/storage/app/media/factinate/2026/6/10/178106161921bf335db129bc09bc08bcf1d80e65d8cc78bef6.jpg)
The Library of Congress, Wikimedia Commons
25. He Launched An Up-And-Comer
Sinatra later said that he learned a lot from Tommy, finding a way to “play” his voice. Sinatra also started to mimic the way Tommy moved and his mannerisms. But there was also a dark side to this working relationship. Sinatra later confessed that he was only afraid of two people in his life: his mother and Tommy Dorsey. Most believe that it was Tommy who launched Sinatra into his incredible fame.
However, this wasn't the only big development in Tommy's life.
Capitol Records (File No. 3860-25). Photographer unknown., Wikimedia Commons
26. He Married A Star
In 1943, Tommy Dorsey married actress Patrica Dane, who had appeared opposite Van Heflin in Grand Central Murder. Once she’d married Tommy, she made the unfortunate choice to stop working, abandoning her burgeoning career. After all, her "prince charming" didn't want her to have a job. This union was a recipe for disaster.
Toronto Star Archives, Getty Images
27. He Got Very Jealous
According to biographers, Tommy's marriage to Patricia was “tempestuous from the start”. The year after they wed, Tommy's notorious temper flashed red-hot during an unforgettable evening. As the story goes, after a night of clubbing and heavy drinking to celebrate Patricia’s birthday, both she and Tommy invited some friends to their apartment on Sunset Plaza Drive.
Little did anyone realize, this was the beginning of a nightmare.
![Gottlieb, William P., 1917-, photographer.
[Portrait of Tommy Dorsey and Beryl Davis, WMCA, New York, N.Y., ca. Oct. 1947]
1 negative : b&w ; 2 1/4 x 2 1/4 in.
Notes:
Gottlieb Collection Assignment No. 113
Reference print available in Music Division, Li](https://www.factinate.com/storage/app/media/factinate/2026/6/10/1781062519015a2b53357f4dac8eeb831573294bfd76afc31f.jpg)
The Library of Congress, Wikimedia Commons
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28. He Lashed Out At A Friend
Enter: action movie star Jon Hall. When Hall arrived at Tommy and Patricia's apartment, he gave Patricia a friendly hug. Unfortunately, an extremely inebriated Tommy didn't think this hug was so harmless. He called Jon out to the balcony—and that's when "the Battle of the Balcony" broke out.
Acme News Photos, Wikimedia Commons
29. He Lost Control
Tommy went from 0 to 100 on Jon, hitting him in the face with a bottle. But the brawl didn’t stop there. Still in full rage mode, Tommy threatened to throw Jon off the balcony. Although it was only the second floor, a fall would have done considerable damage. Jon's only defense against the outraged Tommy was to threaten to take him over the edge with him.
That's when Patricia jumped into action.
30. His Neighbor Was A Gangster
The conclusion of poor Patricia's birthday was a mess, but she also knew she needed to break these two men apart before they did some serious damage to one another. She reportedly ran next door, enlisting the help of the neighbor, Allen Smiley...who just happened to be a gangster in cahoots with Bugsy Siegel.
The entire ordeal was shaping up to be a real-life thriller—and it was about to get even darker.
John Springer Collection, Getty Images
31. He Knew How To Punish A Rival
Once Smiley entered the picture, the details surrounding the tussle become murky. It didn't help that none of the witnesses were able to give a solid account of what actually transpired. The consequences, however, could not be debated. Jon Hall took the brunt of the injuries and—after driving himself to the hospital—needed a whopping 50 stitches. Hall’s doctor later claimed that his wounds were made by something as lethal as a surgeon’s blade.
"The Battle of the Balcony” became legend—but Tommy wasn't done fighting over his wife.
33. They Shared The Same Woman
Before she’d married Tommy Dorsey, Patricia Dane had had an affair with his brother Jimmy. Somehow, it was Jimmy who got upset by this. When he attended his brother’s birthday party, he decided to get some revenge. He rudely shoved a piece of birthday cake right in Patricia’s face. To no one’s surprise, both brothers started fighting.
Tommy may have been on his wife's side on this occasion—but at other times, he was her aggressor.
34. She Had Two Good Reasons
By the summer of 1947, Tommy's marriage to Patricia was over. She blamed their failed union on two things: Tommy’s constant traveling and “extreme mental cruelty”. Strangely, some called the divorce “amicable”. But Patricia paid an awful price. When she started working again, she could only find roles in low-budget films. Once again, it seemed like another woman's career had been upended by Tommy.
One film Patricia would certainly not be working on was the one telling the story of Tommy Dorsey’s life.
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35. They Told Their Story
In 1947, United Artists had the idea to tell the story of Tommy and Jimmy Dorsey in The Fabulous Dorseys. They obviously didn’t know much about Tommy’s terrible temper because they decided to make it a musical comedy, although an alternative title was The Fighting Dorseys. The film was a financial failure, and they had to sell it to the bank.
If this wasn’t a big enough problem, now Tommy had to face a crisis of style.
film screenshot, Wikimedia Commons
36. He Became Old Fashioned
There was one thing Tommy Dorsey hated, and that was the bebop jazz style. Sadly, it was bebop that was taking over from the swing style he loved. Dance halls started closing, as music lovers started to associate swing music with WWII, and it seemed they wanted to forget them both. Stubborn as always, Tommy refused to modernize, but managed to keep selling his nostalgic sound to music lovers.
He saw the writing on the wall, and he knew he had to invest in the next big thing.
37. He Bought A Club
Back in 1944, Tommy had opened a club called the Casino Gardens in Los Angeles. Mostly, because he was angry at the Hollywood Palladium. That’s what he did. When he felt offended, his first instinct was to drive what or whoever insulted him out of business. One night, while he was perusing the crowd at his club, he laid eyes on a woman. It was a fateful encounter.
38. She Surprised Him
The woman he laid eyes on was Jane Carl New. He went over to her table, and she started flirting quite shamelessly and with a little sass. This was something that the scary Tommy Dorsey usually did not experience. He liked her attitude, and they left the club together. This was about to get serious.
Michael Ochs Archives, Getty Images
39. He Tried A Third Time
As it turned out, Jane was a chorus line dancer in Miami. To keep her close, Tommy offered her a job. She could become the manager of the space where his performances took place. Sometime during the winter of 1948, he proposed with a five-carat ring. On March 27, 1948, they tied the knot in a very unpretentious ceremony.
Tommy was happily married, and he thought it was time for a reunion.
40. They Reunited
In 1953, Tommy reunited with his brother, and they appeared on The Jackie Gleason Show. They were so popular that they took over Gleason's time slot for the summer with a show called Stage Show. In 1956, the brothers hosted none other than Elvis Presley. What happened with Presley would go down in history.
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41. They Angered The Network
Most people know the story about Presley’s infamous appearance on The Ed Sullivan Show, where they didn’t dare let the camera go below his gyrating hips. But it was actually Tommy and Jimmy Dorsey who introduced Presley to TV cameras in January 1956. His act was so suggestive that the producers had to apologize for airing it.
The good news was that this TV gig had brought the brothers back together.
Charlie Gillett Collection, Getty Images
42. His Life Seemed Better
Tommy Dorsey seemed to have reconciled with his brother. He also seemed to have a marriage free of his usual drama. He and Jane even had two children, Catherine Susan and Steve. On the outside, it looked as though he had finally settled down. But from the inside, some of his old patterns began to rear their ugly heads.
Michael Ochs Archives, Getty Images
43. It Was A Normal Day
As it turned out, this marriage was not so different from his others. Wife number three ultimately filed for divorce, too. However, a tragic twist of fate ensured that the two would be married until the very end... On November 25, 1956, Tommy and his brother played at the Statler Hotel, where they had a five-year contract.
He arrived home in the morning, did some gardening, and spent some quality time with the kids. He then had dinner with his wife and her mother at home. This would be his final meal.
44. He Was In A Good Mood
After dinner, Tommy told his wife that he would go to his room, watch TV, and then sleep late the next morning. Jane later said that her husband was in a good mood, despite the fact that they were about to start divorce proceedings. It was 9 pm when Tommy went to his room. He would not come out alive.
45. He Locked Himself Away
By 2 pm the next day, Tommy Dorsey had not come out of his room. Jane went to check on him and found his bedroom door locked. This was not unusual. However, Jane must have had a bad feeling. In the end, Tommy’s business manager, Vincent Carbone, investigated the situation, climbing in through the window to see if the snoozing musician was okay. But what he discovered was downright horrifying.
46. They Found Him
To his horror, Carbone found Tommy’s lifeless body. He was fully clothed. Jane couldn't believe the tragic news, but for her, there was more heartache to come. The authorities asked her difficult questions, insisting she recount the events leading to Tommy's demise. Then they found something in the bathroom that revealed a shocking piece of the puzzle.
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47. His Demise Seemed Suspicious
When the authorities found an empty bottle of sleeping pills in Tommy's bathroom, they suspected he had taken his own life. However, only an autopsy could reveal the whole truth. As it turned out, Dorsey had been using sleeping pills for quite some time. So, the empty bottle didn't necessarily mean he’d purposefully overdosed.
48. He Choked
Tragically, the autopsy revealed that Tommy had choked on his own vomit, and that his sedated state had contributed to his passing. However, in the bedroom, they found one other thing: a note. And what it said may have been the most heartbreaking part of all.
49. He Left A Note
Writing notes was Tommy’s usual way of communicating. The one they found in his locked bedroom was ordinary and somewhat sweet. He thanked his wife for the dinner, asked her to thank her mother, and to kiss their daughter Susie for him when she went to school. It was his last communication.
Now the world had to say goodbye.
Pictorial Parade, Getty Images
50. A Friend Was Not A Friend
While there was a large funeral in Tommy's honor, there was one noticeable absence. They asked Frank Sinatra, whose career Dorsey had launched, to take part in the memorial. Sinatra refused and said his presence would be inappropriate. When asked why, Sinatra simply said, he “didn’t like him”.
Apparently, Sinatra had a good reason for this.
![Gottlieb, William P., 1917-, photographer.
[Portrait of Frank Sinatra, Liederkrantz Hall, New York, N.Y., ca. 1947]
1 negative : b&w ; 4 x 5 in.
Notes:
Gottlieb Collection Assignment No. 455
Reference print available in Music Division, Library of Congre](https://www.factinate.com/storage/app/media/factinate/2026/6/10/1781065637ae4941c51b16ed613e1bbfdf62d69cf8f936f1b4.jpg)
The Library of Congress, Wikimedia Commons
51. He Wouldn’t Let Him Go
Back when Frank Sinatra was just getting big, he had a contract with Tommy Dorsey. When he wanted out of the orchestra to go solo, Tommy wouldn't let him. Apparently, his contract said that if he left, Sinatra would have to pay out 43% of all his future earnings: all to Tommy and his agent. Sinatra ended up having to fork over $75,000 just to become a free man.
Another man who must have been feeling free was Tommy’s brother Jimmy.
52. He Couldn’t Live Without Him
With Tommy out of the picture, Jimmy took over as the lead of the orchestra. But this would not last for long. Just as he took over for his brother, he received a devastating diagnosis. Jimmy had throat cancer. On June 12, 1957—just six months after his brother—Jimmy also passed.
The future of the Dorsey Brothers was now in one person’s hands.
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53. She Owned His Name
Strangely, the owner of the name “Tommy Dorsey” was Dorsey’s widow, Jane. So, Jane had to give the okay when Warren Covington took the helm. They renamed the band the Tommy Dorsey Orchestra Starring Warren Covington. Jane wisely kept her husband's full name in the title.
But there’s reason to believe that, despite their fighting, Tommy really had found true love with his third wife.
54. She Loved Him Till The End
Jane passed on August 28, 2003, and she requested her burial to be beside Tommy at the Kensico Cemetery, in Valhalla, New York. Yes, they had been starting divorce proceedings, but she must have still loved him. In fact, her son later said that his mother never got over losing Tommy Dorsey.
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Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,
