A Gettysburg College teammate of Eddie Plank, Winter was not signed by the Athletics because Connie Mack believed he was too small to pitch in the ML at 133 pounds. Winter joined the Red Sox instead, put on 20 pounds, and won 16 games for them in 1901, the AL’s first year, and another 16 in 1905. He was 9-8 for the 1903 champions but did not appear in the WS, as Boston used only its three 20-game winners Cy Young, Bill Dineen, and Long Tom Hughes, in the eight games. Instead, Winter served as a ticket taker. A Red Sox official had scalped all the reserved-seat tickets in the grandstand, affecting the players’ share of the receipts. The players decided to print and sell their own tickets to the games in Boston. Winter and Jake Stahl supervised. In 1908 he was sold to the Tigers. He pitched one inning of the 1908 WS, his last ML appearance.