Winter played eight seasons in Major League Baseball, from 1901 through 1908, for the Boston Americans/Red Sox (1901–08) and the Detroit Tigers (1908).

Winter attended Gettysburg College, where he was a teammate of future Hall of Famer Eddie Plank.

The Philadelphia Athletics passed on signing him because their owner and manager, Connie Mack, believed he was too small to pitch in the major leagues.

[2] Winter was chosen to start on Opening Day of the 1903 season, defeating Rube Waddell and the Philadelphia Athletics, 9–4, at Huntington Avenue Grounds.

He also wound up pitching in the game in which the Americans clinched the pennant, although he did not play in the 1903 World Series as Boston used only Cy Young, Bill Dinneen and Long Tom Hughes.

[6] Winter died in Franklin Lakes, New Jersey at age 73 and was interred at Riverview Cemetery in Wilmington, Delaware.