Red Sox History: Ranking the biggest ‘What Ifs’ in franchise history

BRONX, NY - OCTOBER 16: Pedro Martinez #45 of the Boston Red Sox pitches against the New York Yankees in the first inning during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)
BRONX, NY - OCTOBER 16: Pedro Martinez #45 of the Boston Red Sox pitches against the New York Yankees in the first inning during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)
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BRONX, NY – OCTOBER 08: Willie Mays #24 of the San Francisco Giants bats during a 1962 World Series game against the New York Yankees at Yankee Stadium on October 8, 1962 in the Bronx borough of New York City. (Photo by Herb Scharfman/Sports Imagery/Getty Images)//
BRONX, NY – OCTOBER 08: Willie Mays #24 of the San Francisco Giants bats during a 1962 World Series game against the New York Yankees at Yankee Stadium on October 8, 1962 in the Bronx borough of New York City. (Photo by Herb Scharfman/Sports Imagery/Getty Images)//

2: What if the Red Sox signed Willie Mays and Jackie Robinson?

The Red Sox of the ’40s and the ’50s had one of the greatest players of all time in Ted Williams, and yet they could have paired him with two others if not for the racism of their management. In 1945, esteemed columnist Dave Egan pressured both the Red Sox and the Boston Braves to integrate their team.  GM Eddie Collins said that claim was baseless, for the Red Sox had never had a request for a tryout by a black player.

In response to this ridiculous statement, black sportswriter Wendell Smith brought three Negro Leagues players to Boston for a tryout, including future icon Jackie Robinson. By all accounts, the players excelled in the tryout, but the Red Sox refused to sign them. Robinson signed with the Dodgers later that year and helped them become the dominant team the Red Sox never were.

History repeated itself only two years later. At the time, the Red Sox had a Double-A team in Birmingham, Alabama who shared a ballpark with the Negro League’s Birmingham Black Barons. This gave the Red Sox first dibs on all the Black Barons players when baseball finally integrated, including their young star outfielder Willie Mays.

Red Sox scout George Digby loved Mays and had a deal in place to purchase the future Hall of Famer from the Barons for only $4,500. Yet when Digby relayed this to GM Joe Cronin and owner Tom Yawkey, he learned that the team “had already made up their mind they weren’t taking on any black players.” Mays went on to sign with the Giants, and the Red Sox were left to imagine an outfield with Willie Mays in center and Ted Williams in left.

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