Barry spent most of his career with pennant-winning teams and was the shortstop in the Athletics’ famous “$100,000 Infield.” A key component of Connie Mack‘s first dynasty, Barry was signed off the campus of Holy Cross and helped the Athletics to World Championships in 1910-11 and ’13. Observers considered Barry vital to the A’s chances. Ty Cobb‘s spiking of Barry in the heat of the 1909 pennant race, depriving Philadelphia of his services, is often cited as the reason Detroit won the flag, even though Barry hit only .215 that season.
Not a great fielder, he was at least reliable, and he led AL shortstops in double plays in 1912. He was rated very highly by contemporaries, although he led in errors in 1910. That year he improved his batting to .259 with 60 RBI, 64 runs, and 52 walks in 487 at-bats. In the World Series, he had three runs scored and three RBI in the Athletics’ 12-5 victory in Game Three. In 1911 he stole a career-high 30 bases and hit .368 in the World Series. The number-seven hitter’s best year came in 1913, when he had career highs in batting (.275) and RBI (85). In 1914 he hit .071 in the World Series as Philadelphia was upset by the Miracle Braves. The disappointed and financially pressed Mack sold stars Barry and Eddie Collins to raise money to prevent further losses to defections to the Federal League.
New Red Sox owner Joe Lannin paid $8,000 for Barry in mid-1915. Used exclusively at second base, he hit .262 for Boston and proved to be the last piece in the pennant puzzle. Boston won consecutive World Championships in 1915 and 1916. Barry played only 94 games, hit just .203, and did not play in the World Series. His winning ways netted him $17,930 in WS shares over the course of his career.
Boston manager Bill Carrigan quit after the season to go into business, and Barry was named to replace him. He won 90 games, just one less than the 1916 team, but finished second to Chicago. As a player, he led AL second basemen in fielding but hit just .214. After spending all of 1918 in the military, he returned to a team, now managed by Ed Barrow, that was being sold off to bankroll new owner Harry Frazee‘s Broadway shows. When Barry hit .241 with only two RBI in 31 games, he was traded back to the Athletics in June. He chose to retire instead of reporting.