Jon Lester probably did not fret too much when he finished second in National League Cy Young voting in 2016, considering he has just won his third World Series ring a few weeks prior. In his second season with the Chicago Cubs, the veteran lefty had one of his better seasons on the North Side. It would end up being the closest he would come to a Cy Young award and his final World Series-winning campaign. Lester officially retired on Wednesday morning after an incredible 16-year MLB career.
2016 would see Lester put up the lowest ERA (2.44) and WHIP (1.016) and fifth-best fWAR (4.2), strikeout total (197) and FIP (3.41) of his career. It was his ninth consecutive season with 30+ starts and his eighth (and final) career season with 200+ innings pitched.
Lester was part of a pitching staff that posted a remarkable 3.15 team ERA and 1.11 WHIP. He was in the Cy Young running alongside teammate Kyle Hendricks, who posted a 2.13 ERA which was the lowest in baseball among qualifying starting pitchers. Eventually, both lost out on the Cy Young award to then-Nationals right-hander Max Scherzer.
While postseason stats do not factor in Cy Young voting, his postseason in 2016 is still worth talking about. In six games (five starts and the relief appearance in Game 7) he pitched to a 2.02 ERA, 3.15 FIP, 30 strikeouts, .209 average against and eight walks in 35 2/3 innings.
Lester was lights-out in the NLCS against the Dodgers, winning co-MVP honors with Javier Baez. His Game 5 start in the NLCS in which he pitched seven innings, only giving up one run helped set the table for the pennant-clinching Game 6 at Wrigley Field. His six-inning, two-run effort in Game 5 of the World Series kicked off the 3-1 series comeback.
Jon Lester anchored the staff of the 2016 World Series champion Cubs
One could say this was Lester’s best season as a Cub by a long shot. Though it is interesting to note that in 2015, his first season as a Cub, he posted a 2.92 FIP and 4.9 fWAR. His accomplishments in 2015 may have been overshadowed by Jake Arrieta’s unreal run that year, and his postseason ERA of 4.50 in two starts being very “meh,” especially by Lester standards.
His first two seasons alone made the six-year deal completely worth it. The Cubs got exactly what they wanted, a veteran to help them win a World Series. Everything else was gravy. Lester did see age start to catch up to him after 2016, but he still had an All-Star season in 2018 and continued to grind on the mound every five days right up till the very end.