Chicago Cubs: Ranking Jon Lester’s biggest starts

Jon Lester has had a lot of big moments since joining the Chicago Cubs. Here are five of his biggest starts since coming over in 2015.

At the end of the 2014 season, the Chicago Cubs were three years into their rebuild under Theo Epstein. The team was drafting many quality young players while also making trades to help slowly build the major league roster. The 2014-2015 offseason was pivotal, as the team hired Joe Maddon to be the manager to take this team to the next level after five straight losing seasons.

On the field, the team needed to sign a big-name free agent to take a giant step forward in their rebuilding process. Left-handed pitcher Jon Lester made sense, as he was one of the best pitchers in the game and had also proven himself in big moments. Maddon called Lester “Plan A” when it came to the team’s offseason plans.

Lester had spent his entire career with the Boston Red Sox, which included two World Series championships, before being traded to the Oakland Athletics during the 2014 season. When he became a free agent, several teams pursued, including the Cubs, Red Sox, San Francisco Giants, and Los Angeles Dodgers. Lester narrowed it down to the Cubs and Red Sox, and in the end, he went with the North Siders, signing a six-year, $155 million deal.

Lester has turned out to be arguably the most important free-agent signing in team history. The Cubs won a World Series and have made four straight playoff appearances since Lester joined the team, and he’s been an essential part of all of it. Many times, he’s come through in big situations. Here we’ll look at five of his most important starts in a Cubs uniform.