He began his professional career in 1916 at the age of 22 and played for nine seasons, until the age of 31 in 1925. He split his career between the major leagues and the minors, spending four full seasons and a part of a fifth at the former level. In the minors, he spent two full seasons at the Double-A level, parts of two seasons at the Double-A level and part of one season at the Single-A level. Based on the record that is available, it is known that he pitched in 106 minor league games, going 36–36 with a 3.70 ERA in 656 innings. He also had 241 at bats, hitting .212 with four doubles.\n', '

He played in the major leagues from 1919 to 1923, appearing in 110 games and going 13–24 with a 5.04 ERA in 405 innings. He allowed 510 hits and 164 walks, while striking out 94 batters. He was used both as a relief pitcher and a starting pitcher, finishing in the top 10 on the National League leader board in games finished and saves multiple times. As a batter, he hit .171 in 117 at bats and in the field, he committed 10 errors for a .929 fielding percentage. He was also involved in six double plays.\n', '

He was a highly touted young player at the onset of his career, being initially compared to Hall of Fame pitcher Christy Mathewson and eventually former 21-game winner Ferdie Schupp. According to contemporary accounts of the time, his assets were many-fold: "He has every physical qualification", stated the New York Tribune, "as well as a varied assortment in the pitching line." He also had a quick pickoff move to first base, with Giants\' manager John McGraw claiming "(Winters) can peg to first base more quickly than any other man in the National League." He performed well in the minor leagues, however a lack of control at the major league level, an indifference towards the game, a lack of ambition and eventually a bad arm ended his hopes of stardom.\n', '

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