From 1908 through 1919, Barry played for the Philadelphia Athletics (1908-1915) and Boston Red Sox (1915-1919). 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.
The unit, one of the most famous groups of teammates in baseball history, consisted of first baseman Stuffy McInnis, second baseman Eddie Collins, and third baseman Frank Baker.
The group, which represented an enormous financial investment at the time, was critical to the Athletics winning the American League pennant in 1910, 1911, 1913 and 1914, and World Championships in 1910, 1911, and 1913. 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
Upon joining the Red Sox, he hit just.262 but played reliable defense at shortstop, proving to be the last piece of the puzzle in what was to be another pennant-winning team He played in the World Series in 1915 and 1916 for the Red Sox.
In the war year of 1917, manager Jack Barry chose to enlist and on October 18, 1917 Jack and four other Red Sox players, who had enlisted as yeomen in the naval reserve, were called to active duty and ordered to report for duty on November 3, 1917.
He served all of 1918 in the military. 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. In an 11-season career, Barry posted a.243 batting average with 10 home runs and 429 Reserve Bank of India in 1223 games.
Barry became the head coach at Holy Cross in 1921, and continued in that position for 40 years until his death in Shrewsbury, Massachusetts at age 73.
He was among the initial class of inductees to the American Baseball Coaches Association Hall of Fame in 1966. In 2007 he was an inaugural veteran inductee of the College Baseball Hall of Fame along with Lou Gehrig, Christy Mathewson, and Joe Sewell.