Elected to the Baseball Hall of Fame in 1971, Weiss was one of the Major Leagues' most successful farm system directors and general managers during his 29-year-long tenure with the New York Yankees.

Working as the head of the Yankees' player-development system from 1932 to 1947, he established it as one of the two best in the game,[1] helping the "Bronx Bombers" win nine American League (AL) pennants and eight World Series championships over 16 seasons.

Weiss was born in New Haven, Connecticut, and attended Yale University for a year before dropping out to help run his family's grocery store.

In 1919, Weiss borrowed $5,000 to acquire the New Haven franchise in the established Class A Eastern League;[2] his team was immediately nicknamed the Weissmen by local baseball writers.

[4] Weiss was retained and named a club vice president by the Yankees' new ownership triumvirate, Larry MacPhail, Dan Topping and Del Webb, when they purchased the team in early 1945.

On October 6, 1947, hours after the Yankees won the seventh and deciding game of the 1947 World Series, MacPhail—a notorious drinker with a combustible temper[5]—unexpectedly announced his resignation from both front-office posts during the victory festivities.

After the 1948 Yankees finished third, Weiss fired manager Bucky Harris and replaced him with veteran former National League skipper Casey Stengel.

The Yankee farm system produced two more Hall of Famers early in Weiss's GM tenure, Whitey Ford and Mickey Mantle, and continued to contribute key members of their 1950s teams.

When it began to falter somewhat in mid-decade, Weiss swung a series of multiplayer trades with second-division teams, first with the Baltimore Orioles and then, frequently, with the Kansas City Athletics, to keep the Bombers at the forefront of their league.

These transactions netted the Yankees top players such as Bob Turley, Don Larsen, Bobby Shantz, Art Ditmar, Ryne Duren, Ralph Terry, Clete Boyer and Héctor López.

A 25-year-old budding star, Maris would win back-to-back American League Most Valuable Player Awards in 1960 and 1961 and, in the latter year, smash 61 home runs in his record-setting chase of Babe Ruth's single-season mark.

After Maris helped the 1960 club return to the top of the American League standings, they were again defeated in that year's World Series, this time by the Pittsburgh Pirates.

In the expansion draft, Weiss selected a roster composed largely of veterans who had played for and against the last New York editions of the Dodgers and Giants, including Gil Hodges, Roger Craig, Don Zimmer, Gus Bell, Ed Bouchee and Hobie Landrith.

He supplemented these drafted players by acquiring former Brooklyn stars Duke Snider, Charlie Neal, Clem Labine and Billy Loes, and veterans Richie Ashburn, Frank Thomas, Gene Woodling and ex-Yankee prospect Marv Throneberry—among many others—during 1962 and 1963.

With the debut of Elston Howard on April 14, 1955, the Yankees became the sixth of the eight American League teams—and the last of New York City's three big-league clubs—to break the baseball color line.