Chicago Cubs: Top 5 Jon Lester moments in a Cubs uniform

There is certainly a case to be made regarding Jon Lester as the best free agent signing in Chicago Cubs history – so let’s celebrate his 35th birthday in style.

After signing with the Chicago Cubs prior to the 2015 season, veteran southpaw Jon Lester helped turn around the franchise and lead them to their first World Series in 108 years just one year later. To call the first four years of his time in a Cubs uniform a success really doesn’t do it justice.

On the North Side, Lester carries a 61-31 record with a 3.26 ERA into 2019. He tied a career-high with 19 wins while finishing as the runner-up in NL Cy Young voting three years ago and narrowly missed that mark in 2018, winning 18 contests for Chicago. Now, wins and losses certainly aren’t everything – but we’ve seen the lefty gut his way to more than a few of those with less than his best stuff.

Lester turned 35 on Monday, and as such we will be counting down the top five moments in his tenure with the Chicago Cubs. The only problem now? Narrowing the list down to just five.