Modern fight managers look back on the career of Leo P. Flynn with awe and, now and then, an attempt to imitate it. It isn't easy to do anymore, what with boxing commissions and new-fangled notions of ethics. A few of Flynn's breed survive—but the best place to look for his type is in some old Mark Hellinger movie on The Late Show, where a jowly, cigar-chewing character is watching his boy take an awful bruising in the ring with the calm of a man who knows that the gate is very good.
"Flynn was the greatest guy boxing ever had," says oldtimer Jersey Jones. "I mean all around—manager, promoter, matchmaker." Unlike most of his free-wheeling contemporaries, Flynn was a wealthy man when he died in 1930. He left behind him a legal estate estimated at half a million dollars and rumors of a safe containing $200,000 in $1,000 bills and a boxful of diamonds. He also left behind possibly the largest stable of fighters ever assembled by an American manager. Guesses on the number of pugilists who called Flynn their manager at any one period range from 30 all the way up to 50.
"I doubt if Leo knew himself," says Ray Arcel, who often trained Flynn's fighters. "I know that some of his fighters never even saw him."
Flynn was a manager in the true sense of the word. He did not cater to the whims of the young men who placed body and soul in his unsentimental hands. "No purse too small, no opponent too tough" was his motto. Flynn's fighters were in action somewhere every night in the week. On one Thanksgiving—so the story goes—19 of them fought in one town or another through the East and Midwest.
"More than half of them got stiffened, too," Flynn chuckled afterward.
He is said to have coined the expressions palooka and ham-donnie, to describe the earnest if inept young men who contributed to his wealth. A Flynn fighter was expected to know his place, and that place implied almost no personal contact with his manager—even at the moment of truth.
"He didn't work in his fighters' corners much in his later years," Arcel recalls. "But I remember he was there at a semifinal in the Garden when a boy got knocked cold. Leo never batted an eyelash. He just stared straight ahead and said to me in that deadpan way: 'Go in and get him.' "
The origins of the man, even of his name, are draped in obscurity. It is agreed that he came from Providence, R.I., but some oldtimers have said that his real name was McManus. Nevertheless, he became Leo P. Flynn early in life; the P stood for Parnell, he claimed. Certain skills came to him as easily as his name. In Providence he had been a jeweler's apprentice, a bricklayer and an amateur boxer. As a dancer of the cakewalk and other specialties of the time, he had acquired a number of prizes in dance competitions and a partner named Katherine. At 19, he married her, and together they went to New York.
"All I had was a carpetbag and a couple of bucks," he said afterward. "The latter belonged to Kate."
"The first time I ever heard of Flynn he was clipping suckers in the pool halls on 14th Street," a contemporary manager has said. But almost imperceptibly Flynn began to mingle with the boxing mob and, before anyone quite realized it, he had built himself a large stable of fighters.
Leo often traveled with his fighters before World War I, and he did not approve of idle hands. One Monday evening he took Johnny (Kid) Alberts to fight in North Adams, Mass. The next morning they started west and Albert fought in a different town every night of the week, finishing with a 10-round bout on Saturday in St. Joseph, Mo.
Damon Runyon said he was the first man to call Flynn "The Carpetbagger," and Flynn relished the name because of the wily larceny it implied. He relished even more the scheming fight managers, all patterned on himself, who peopled Runyon's stories.
"I always carried a carpetbag in the early days," Flynn said. "When the dough was scarce, you could just drop the bag out the hotel window and pick it up once you skipped past the room clerk."
In more prosperous times Flynn had an office in midtown Manhattan where an aide, Arthur Yende, entered on a big board the names of Flynn's fighters and their schedule of bouts. In towns all over the country local promoters knew they could fill half a boxing card any night by placing a call to Flynn. If Leo was out, his wife would "take the order" and drive as hard a bargain as her husband. To supply three fighters for the three 10-round bouts that might have been scheduled on any given program, Flynn would ask for, and usually receive, 45% to 50% of the gate.
At the beginning of each week, Flynn's fighters would visit his office, learn their schedule from the big board and catch the next train to the provinces. They seldom knew whom they would fight and never how much they would make. After the fight, or fights, they would return to New York to pick up their purses, the size of which had been determined by Flynn. Anyone not satisfied was free to find another manager, but Leo never suffered a scarcity of fighters. Everywhere in the country the word was out that if a boy wanted fights, Leo P. Flynn could provide them.
In time, the old pool shark, now prematurely gray, began to gather the trappings of affluence. He was the first boxing manager to own a Rolls-Royce, and one of his fighters usually served as a chauffeur. He bought a large house on the Grand Concourse in the Bronx and gradually dissociated himself from the grimy intimacies of the boxing business. It became an event of sorts when Flynn, a covey of Irish politicians in tow, condescended to visit the gym or a local fight club.
Probably one of the few fighters to obtain financial satisfaction from Flynn was an otherwise unfortunate young man whom we shall call Joey. Defenders of boxing insist that Joey did not have all his marbles when he entered the game, but it is certain that neither his association with Flynn nor the merciless opponents Leo found for him did anything to better his health, mental or physical. Like many a character of fiction, Joey at last wound up among the flotsam of Broadway, bumbling along the street with glazed eyes and a slack jaw.
Now it happened that Flynn, to secure the services of this willing worker, had guaranteed him a minimum annual sum of money. After Joey "retired," Flynn openly bragged that he had pocketed the large balance owed to his fighter, and for a short while it never occurred to Joey to demand payment in full on his contract. But every day when he wandered past the building on Broadway where Flynn kept his office, there, ostentatiously parked at the curb, was Flynn's Rolls-Royce.
"See that car. Joey," lounging members of the boxing mob would call to him. "You paid for that."
Suddenly a sense of having been wronged came to Joey. He got himself a lawyer and brought suit against Flynn for the $12,000 still owed to him. Leo was furious.
"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.