Chicago Cubs: Lester best free agent signing in franchise history?

Chicago Cubs starting pitcher Jon Lester is still going strong despite being 35 years old now. Is he the best free agent signing the Cubs have ever had?

When the Chicago Cubs landed Jon Lester in the 2014 offseason, many people questioned what he was doing leaving a talented Red Sox team for a rebuilding team in Chicago. Obviously, the money was a big factor, but Lester knew what he was getting himself into and winning was not a guaranteed thing.

At the time, Lester was coming from a Red Sox team that had won two World Series championships during his tenure there. In nine seasons in Boston, he had a 3.64 ERA which included a no-hitter in 2008 and a 3-0 record with a 0.43 ERA in his World Series starts. It was a risky move for both sides, as Lester was approaching 31 years of age just after being signed. With a six-year contract, the Cubs were hoping they would at the very least get the best version of Lester within the first couple of seasons.

He got off to a rough start in a Cubs uniform, pitching to the tune of a 6.23 ERA in April 2015. I recall a particularly vocal fan on Opening Night against the Cardinals yelling “Go back to Boston”, which could be heard on the television broadcast. Lester would go on to finish the 2015 season with a normalized 3.34 ERA due to the assistance of a 1.66 ERA in the month of July.

Lester finished the 2016 season with the best ERA of his career (2.44). He was named the 2016 NLCS Co-MVP as well as the Cy Young Award runner-up on the way to helping the Cubs win their first World Series title in 108 years. Lester was the only Cubs starting pitcher with World Series experience and I am not sure they complete that comeback without him. If you recall, he pitched in relief in the decisive Game seven.

"“There is an incredible amount of calm that I’m seeing from the dugout when I’m watching him out there right now,” Cubs manager Joe Maddon said. “He’s really, really in the moment, he’s calm. Gosh, he’s just eager to get out and pitch. – via MLB.com"

I figured after about his fourth season with the Cubs that we would start to see some regression from Lester, as is common with players that get older. However, Lester has looked brilliant this season. Through five starts, he has pitched 26.0 innings with a 1.73 ERA. He is averaging his highest strikeouts-per-nine-innings (K/9) since 2010. That season Lester finished with a record of 19-9 and a 3.25 ERA.

I think what most impresses me about Lester this season is that even though his fastball is down a couple of notches, averaging just over 90 mph, he’s been extremely effective locating his pitches. He’s actually using his fastball less than previous seasons and relying more on his cutter with a career high 33.9 percent of his pitches (via Fangraphs).

Lester missed two starts due to a hamstring injury he sustained when sliding into home plate in the home opener. However, he did not require a rehab start with the Triple-A squad and looked like he had never been gone. In his last start against the Mariners, who like to hit a lot of home-runs and take a lot of walks, Lester was masterful while pitching 7.0 innings , striking out eight batters, and walked just one guy.

"“I think we were able to just use that layoff almost to regroup a little bit physically on my shoulder and elbow. It was just a matter of making sure the leg was OK coming back,” Lester said. “I felt like my arm was good, my mechanics were good and it just kind of carried over to the last few starts.” – via DailyHerald"

Jon Lester has another guaranteed season with the Cubs in 2020 and has a $25 million team option in 2021 with a $10 million buyout (via Spotrac). He has been worth every penny that the Cubs gave him.

Can you think of a better free agent signing?