Looking at 4 of the worst free agent contracts in Chicago Cubs history

With no end to the ongoing MLB lockout in sight, we’re left scrambling for crumbs of news from beat writers, desperately hoping for something big. Earlier this week, we got confirmation of ‘mutual interest’ between the Chicago Cubs and Carlos Correa, perhaps setting the stage for one of the team’s highest profile free agency pursuits in some time – maybe ever.

The team is also reportedly wary of long-term deals and are hesitant to get into that 10-year range in terms of contract length. After all, a 10-year bust is hard to dig out from under. Don’t believe me? Well, look at some of these past nightmares – and none of them were anywhere near a decade long in length (thankfully).

4 of the worst free agent contracts in Chicago Cubs history: Edwin Jackson

Did you know the Cubs paid Edwin Jackson $13 million to not pitch for the during their 2016 World Series run? You do now. One of the biggest swings-and-misses of the Theo Epstein era, the right-hander never came remotely close to being a worthwhile investment during his time in Chicago.

Inked to a four-year, $52 million deal ahead of the 2013 season, Jackson kicked things off by losing a league-high 18 games that year, allowing more than 10 hits per nine. If you think things got better from there, you’re sorely mistaken.

In 2014, Jackson was actually much, much worse than the year prior. His ERA ballooned from 4.98 to 6.33 as he went 6-15. In his defense, his FIP both years was semi-respectable, but no one remembers any of that when you are as ineffective as he was.

He got the chance to compete for a spot in the rotation the following spring, lost that battle to Travis Wood and headed to the bullpen as the long man. He pitched well, but Chicago still designated him for assignment in July, eating his salary not only for that year, but, as I noted, the following season, as well.

All Jackson has going for him is this: he’s the only player in big league history to play for 14 different franchises. As far as Cubs fans are concerned though, he represented a massive whiff from Epstein in the early years of his tenure.