Dartmouth as a pro baseball career offered him financial security, which would enable him to help his mother. He did not play in the minor leagues but went straight to the Red Sox, making his debut on August 25, 1926 against the Detroit Tigers as a reliever. He was the first pitcher in the American League to wear eyeglasses, which corrected for near-sightedness. After one more relief stint, MacFayden made his first start against the legendary Walter Johnson of the Washington Senators on September 4, 1926. He lost 5–1, throwing a complete game. In 1928, he was the Boston Red Sox's Opening Day pitcher, making his season debut in Griffith Stadium in Washington, D.C. with another native New Englander, President Calvin Coolidge in attendance. He won 7–5. In his five years with the Red Sox, he was a relatively mediocre pitcher with an abysmal team, though he did lead the league with four shutouts in 1928, a year he went 10–18 with a 3.62 ERA. In 1932, after going 1–10 to start the season, he was traded to the New York Yankees for pitchers Ivy Andrews and Hank Johnson and $50,000 in cash. Both pitchers were on the disabled list at the time, but the trade seemed lopsided in favor of the Red Sox. The speculation was that Yankees owner Jacob Ruppert was trying to keep MacFayden away from contending teams. Ruppert might have been thinking of MacFayden's stellar performance against the Yankees on May 24, 1929, the year he led the league in shutouts. In a game he started at Fenway Park, MacFayden shutout the famed "Murderer's Row", throwing a four-hitter. He did load the bases with no outs one inning, but then retired the heart of the order, Lou Gehrig, Babe Ruth, and Tony Lazzeri, striking out both Gehrig and Lazzeri. New York Yankees In his 17 games for The Bronx Bombers in the 1932 season, 15 were starts, and he went 7–5 with a 3.93 ERA. The Yankees, anchored by Hall of Famers Babe Ruth, Lou Gehrig, Tony Lazzeri and Bill Dickey among position players and Hall of Fame starting pitchers Lefty Gomez, Herb Pennock and Red Ruffing on the mound went on to win 107 games and sweep the Chicago Cubs in the World Series. The Yankees' post-season roster carried only six pitchers, however, and MacFayden wasn't one of them. He would never again be on