You know one of the strange things you find out when you study baseball history is that no matter how good a particular player is, he usually, but not always, ends of on a team that puts up a regular season losing record at some point. Babe Ruth did it in 1935, Mickey Mantle did it in the last couple of years of his career. Deadball player Jack Barry never did.
Barry was born in Connecticut in 1887. He played ball locally, then transferred his talents to Holy Cross. Connie Mack found him in 1908 and signed him to play with the Philadelphia Athletics. He became the shortstop of the “$100,000 infield” (Stuffy McInnis, Eddie Collins, Barry, Frank Baker first to third), the premier infield of the day. The $100,000 had to do with what the infield was worth, not what they were paid. He became part of the first Athletics dynasty that won the World Series in 1910, 1911, and 1913, then lost the Series in 1914. He stayed with the A’s into 1915, then found himself sold to the Boston Red Sox for $8000. The A’s ended up with a terrible record. The Sox went to the World Series.
With Barry at shortstop (longtime shortstop Larry Gardner went to third base), the Red Sox won the World Series in five games over the Philadelphia Phillies. The Red Sox promptly went out and won the 1916 World Series too, although Barry, by now a second baseman, missed the Series. So in consecutive years from 1910 through 1916 Barry was on five World Series winners, one World Series loser, and saw his team miss the Series exactly once (1912). Not bad, right? Well, it was the end of the streak. In 1917, Red Sox manager Bill Carrigan retired from the dugout. Barry replaced him and led the BoSox to second place. It was his only year as manager, Ed Barrow taking over in 1918.
Barry left the managerial job not because he wasn’t any good at it, but because the United States entered World War I. Barry joined the military and missed the entire 1918 season. Under Barrow, the Red Sox went back to, and won, the World Series. So there was no managerial job waiting for Barry when he returned in 1919. He played in 31 games in 1919, then was sold back to the Athletics. Rather than report, he retired.
Over his career, Barry hit .243, slugged .303, had on OBP of .321 (for an OPS of .624), stole 153 bases, had 1009 hits, 532 runs, and 429 RBIs. His fielding was consistently among the league leaders, but he was never the most accomplished shortstop (or second baseman) in the AL. His World Series number mirror his regular season play very well. In 25 World Series games he hit .241, slugged .345, and had on OBP of .272 (for an OPS of .617), all very close to his career percentages. His managerial record was 90-62.
Barry was through with the Major Leagues, but not with baseball. In 1921 he took over coaching duties at Holy Cross and remained there the rest of his life. His career .806 winning percentage is a college record.
But the title says “six-time winner” and you’ve only counted five, right? Well, in 1952 he took Holy Cross to Omaha where they won the College World Series. Still coaching the team, he died in April 1961. Of the $100,000 infield, only Frank Baker outlived him. In 1966 he was one of the initial inductees to the College Baseball Hall of Fame. Not a bad outcome for a .243 hitter.