Cubs News: A look back at five of Theo Epstein’s worst moves

Chicago Cubs: The ill-fated Edwin Jackson signing

The Cubs were not ready to contend before the 2013 season. Sure, they needed some major league players to help fill their roster, but it was ill-advised to give any big deals to any free agent, much less someone like Edwin Jackson, who prior to 2013 was a decent, if not great, major league starting pitcher.

Jackson has been all over the place in his major league career, including before coming to the Cubs. He was with the Rays in 2008, the Tigers in 2009, the Diamondbacks and White Sox in 2010, the White Sox and Cardinals in 2011, and the Nationals in 2012. In each of those years, he made at least 31 starts and posted an ERA under 4.50 each year.

Jackson was able to turn that moderate success into a four-year, $52 million deal with the Cubs prior to 2013. That success did not continue; in 2013, he led the league in losses with 18 (albeit on a bad team) while posting a 4.98 ERA. The next year was much worse: In 28 games (27 starts), he posted a miserable 6.33 ERA.

As a reliever, Jackson actually wasn’t horrible in 2015, posting a 3.19 ERA in 31 innings before the Cubs were able to trade him to the Atlanta Braves. Still, it ended up being a terrible signing for the Cubs. Jackson, meanwhile, bounced around to several more teams and amazingly was still in the majors as late as 2019.