Ungentlemanly Facts About Tommy Dorsey, The Bandleader With A Harsh Tone

Ungentlemanly Facts About Tommy Dorsey, The Bandleader With A Harsh Tone


June 11, 2026 | Sammy Tran

Ungentlemanly Facts About Tommy Dorsey, The Bandleader With A Harsh Tone


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. 

(Original Caption) 1956-New York, NY: Frank Sinatra and Tommy Dorsey turn back the clock as they prepare to rehearse their upcoming stage show at the Paramount Theatre, where Frank's new starring motion picture, Bettmann, Getty Images

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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. 

circa 1955: Studio portrait of American jazz bandleaders Jimmy (1904 - 1957)(L) and Tommy Dorsey (1905 - 1956), smiling in front of a white backdrop. Hulton Archive, Getty Images

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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. 

(Original Caption) 1941- Tommy Dorsey and his band. On the far right in the last row is a very young and yet unknown Frank Sinatra. Movie Still from, Bettmann, Getty Images

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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. 

16th October 1944: EXCLUSIVE American jazz bandleader Tommy Dorsey (1905 - 1956) dances with a young woman as a man plays the piano. Gene Lester, Getty Images

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Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,