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.