Chicago Cubs: Comparing the Cubs and White Sox rebuilds

Cubs Free Agency Signings

December tended to be a busy month for the Cubs, who made numerous splashes in free agency in back to back Decembers. It started off with a bang with Jon Lester inking a six-year, $155 million deal with the Cubs in December of 2014 and was topped off with a surprise appearance by Dexter Fowler in spring training.

Numerous reports had stated that Fowler was on the brink of signing a multi-year deal with the Baltimore Orioles during the 2015-16 offseason, but Dex returned to the Cubs on a one-year deal. The rest is literal history.

Let’s check out the significant free agency signings that the Cubs completed during their rebuild and contention.

Jon Lester (December 15, 2014)

Lester’s arrival on the North Side was a blatant indicator that it was time for the Cubs to start contending. The Cubs had studied the Theo Epstein School of Rebuild and stockpiled young, offensive talent through drafts and trades. Now it was time to add the pitching and veteran experience via free agency. Lester was the first of those pieces to fall into place. It’s also worth noting that the Cubs added veteran catcher and Jon Lester catching partner David Ross about a week later.

Ben Zobrist and John Lackey (December 8, 2015)

December 8 was a very busy day for Theo and Company. In an unusually eventful day at the Winter Meetings, the Cubs signed veteran super-utility man Ben Zobrist and starting pitcher John Lackey heading into the 2016 season. In doing so, the Cubs rotation was set for their championship season.

Jason Heyward (December 15, 2015)

There’s no doubt that Christmas 2015 was one hell of a party at the Heyward household. Just ten days before Christmas, Heyward inked a massive 8-year, $184 million contract to join the Cubs from the hated St. Louis Cardinals. (Side note in case any Cardinal fan is reading this…Heyward actually took less money so that he could leave St. Louis).

Dexter Fowler (February 25, 2016)

Yes, Dexter Fowler’s name is mentioned in trades and free agency. That’s not a typo.

As we touched on just a second ago, Fowler was reportedly close to signing a multi-year deal with the Baltimore Orioles. Instead, he shocked fans and players alike by suddenly showing up to spring training a couple of weeks before the season started and announcing that he had returned to the Cubs on a one-year deal for the 2016 season.