Ranking the top 5 free agent signings in Chicago Cubs history

5 best free agent signings in Chicago Cubs history: #1 – Jon Lester

Look, if you made it this far, odds are you know how this ends. With Big Jon fist pumping as he stomps off the mound in Cleveland five-plus years ago, on the brink of doing what so many others had tried and failed to do over the last 108 years.

Jon Lester changed everything when he came to the Chicago Cubs prior to the 2015 season. He, along with the hiring of Joe Maddon as manager, put an end to the acceptance of losing that had long taken hold of the franchise and set a new tone forward.

Lester flirted with 20 wins not once, but twice, with the Cubs – winning 19 during his NL Cy Young runner-up 2016 season then 18 two years later. A pair of All-Star appearances, a bulldog mentality that permeated throughout the dugout and clubhouse when he started and some of the grittiest pitching performances I’ve seen as a Cubs fan.

When you not only come to a team to change the culture and expectations, but deliver on said change, you earn a special place in the history books. Lester helped end not one, but two, of the most infamous title droughts in sports – and his exploits in Chicago won’t soon be forgotten.