Born in Meriden, Connecticut, Barry spent his nearly entire tenure in the big leagues on winning teams, first the Philadelphia Athletics and later the Boston Red Sox.

Athletics manager Connie Mack signed Barry off the campus of the College of the Holy Cross to play shortstop on what would become his famous $100,000 infield.

In 1915, the year after the Boston Braves swept the Athletics in the World Series, Red Sox owner Joe Lannin paid $8,000 for Barry's services, as Mack was dismantling the team.

After poor play in 1919, he decided to retire rather than be sold away in another fire sale following Harry Frazee's decision to sell his shortstop back to the Athletics.

[1] In 1943 he became Holy Cross' acting athletic following the death of Tom McCabe and remained in that role until Gene Flynn returned from the United States Army in 1946.