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Weiss became the baseball entrepreneur of New Haven, CT while attending Yale. His semi-pro team outdrew the local Eastern League club, as Weiss gave the fans what they wanted - big-name stars and Sunday baseball. Ty Cobb demanded $350 for his first game; Weiss gave him $800, and Cobb returned to New Haven frequently. Finally, in 1919, the out-promoted Eastern League club sold out to Weiss.
Upon joining the Yankees in 1932, Weiss built a farm system which at one point boasted more than 20 teams. At Newark (International League), such standouts as Joe Gordon and Charlie Keller were developed. Weiss sold off surplus talent, those players not quite up to Yankee standards. When he was farm director, his bosses were Ed Barrow (who had hired Weiss), and later Larry McPhail. There was a coolness in Weiss's relationship with the territorial Barrow, though the two were much alike. MacPhail, who bought the Yankees in 1945 with Dan Topping and Del Webb, alternately snubbed and abused Weiss. MacPhail brought a turbulence to the Yankees that Topping and Webb eradicated by buying him out in 1947. Weiss was then named GM with absolute authority. As a baseball man rather than a MacPhail-type showman, Weiss ran the club, like Barrow, along conservative lines. When the Yankees finished third in 1948, Weiss fired manager Bucky Harris and hired Casey Stengel. Many felt that Weiss had blundered, that he had hired a clown to manage the Yankees. But Weiss knew the real Stengel, who would reward his faith with 10 pennants in 12 seasons.
Weiss surrounded himself with exceptional people, including a brigade of crack scouts. In 1934, when his scouts told him an injured minor leaguer named Joe DiMaggio would recover and be a star, Weiss convinced owner Jacob Ruppert that the Yankees had to have him. In 1959, he pried Roger Maris from the Kansas City Athletics, offering a package (which included Hank Bauer and Don Larsen) that the second-division club could not refuse. Dealing with old friend Arnold Johnson, the A's owner, and former employee Parke Carroll, the A's GM, Weiss consistently strengthened the Yankees. "It must be great," said Indians GM Hank Greenberg, "to have your own farm system in the same league."
Weiss was iron-fisted at contract time. He liked to say of his agentless players, "The boys have to be hungry for that World Series money." But Weiss expected his low-salaried players to be well-behaved gentlemen. Billy Martin didn't fit into the GM's idea of the Yankee image, and as soon as he had an excuse (the infamous fight at the Copacabana club), Weiss traded him.
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