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"I'll never pay that crazy kid a cent," he vowed.
Flynn's lawyer, who often had observed Joey moving along the street in his grotesque little dance, felt otherwise. "Leo," he said, "if they ever put that poor guy on the stand and the jury gets a look at him, they'll hand him $100,000!"
Flynn settled out of court.
When Tex Rickard began to promote fights in Madison Square Garden, he asked Flynn to be his matchmaker. It is said that Flynn accepted the job without pay. However, after 18 of Leo's fighters appeared in main events there within a short time (only one of them won), other managers complained. The boxing commission decreed that he could not act simultaneously as manager and matchmaker, and he departed the Garden. Later, in 1926 when Jack Dempsey split with his longtime manager, Jack Kearns, Flynn became Dempsey's advisor. It was during this period that he lost his most tumultuous argument—that of trying to convince boxing officials that Dempsey deserved the victory in his "long-count" battle with Gene Tunney. Dempsey was so impressed by Flynn's acumen that he promised to engage him as his manager if he ever came out of retirement. The former champion also presented Kate Flynn with a $9,000 diamond brooch, "for keeping my food from getting contaminated," by supervising his training kitchen before his bout with Jack Sharkey.
As boxing plunged with the rest of the world into the Depression of the 1930s Flynn's attention wandered from the sport. He had managed, over the years, many notable fighters—among them Bill Brennan, Panama Al Brown, Dave Shade, Kid Norfolk and Panama Joe Gans. His operation had grown self-sustaining. Moreover, various boxing commissions were taking a disapproving look at his purported financial interest in the promotion of bouts in which his fighters took part. He also was accused of supplying fighters for bootleg (unlicensed) bouts.
Suddenly Flynn discovered a bright new horizon in the game of golf. Puzzled visitors to Flynn's Broadway office found him chipping trick shots into a straw hat, which he had placed upside down on a swivel chair. Moving in moneyed circles now ( John McGraw of the Giants and other celebrated New Yorkers were his frequent companions), Leo's agile mind made several important observations. He learned 1) that his skill on a pool table carried over to the putting greens and 2) that men with inflated notions of their own skills were as easy to locate at the New York Athletic Club as they had been on 14th Street.
On a damp spring day in 1930, Flynn made an appointment to play golf at Van Cortlandt Park with an affluent sportsman whose delusions he had carefully nurtured. Kate pointed out that he had a bad cold and suggested he cancel the appointment. But Leo was unable to turn his back on a primed gull. He played that damp day, won a sizable bet and contracted pneumonia. A few days later, The Carpetbagger, aged 51, was dead, undone by big purses and easy opponents.