Greg Maddux: 1992
Prior to his historic decade-long stretch with the Atlanta Braves, Greg Maddux was the ace of the Cubs pitching staff from 1988-1992. His contract year with the Cubs in 1992 was the most impressive of his Cubs tenure, where he led the league in wins (20), games started (35) and innings pitched (268) while playing to a 2.18 ERA in his Cy Young campaign.
Although Maddux left that offseason, 1992 kicked off four consecutive years of National League Cy Young awards for the Hall of Famer. Randy Johnson is the only other pitcher in MLB history to match that record and both men are also the only pitchers to do it three times in a row.
Despite securing the Cy Young award, Maddux and the Cubs could not come to an agreement on a contract extension, and he left to play for the Braves on a five-year $28 million deal. Although a pitcher of Maddux's caliber would be making close to or more than $28 million in a single season, Maddux's contract with the Braves made him the fourth highest-paid player in the league at the time.
Maddux is truly one of the best pitchers who ever played for the Cubs and he left the league an all-time record of 18 gold gloves (which stands today), four Cy Young awards, eight All-Star appearances, and a World Series ring. The Cubs retired his number 31 in 2009 and he was inducted into the National Baseball Hall of Fame in 2014.