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

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He did a lot of good. But here are Theo Epstein’s five-worst moves with the Cubs.

The Chicago Cubs have a new President of Baseball Operations in Jed Hoyer, as Theo Epstein has departed. Epstein brought a championship to Chicago in 2016, and for that, we will always be grateful. We previously looked back at his best moves with the team.

However, Epstein made his share of mistakes with the club. Here we look at five of his worst moves during his time with the club from 2011 to 2020.

Chicago Cubs: Drafting Brendon Little right before Nate Pearson in 2017

The Cubs had a lot of success with first round picks under Epstein. Kris Bryant, Kyle Schwarber, and Ian Happ are among those that have worked out decently to this point. However, there are a few first round picks that Epstein has missed on.

One move that might get some scrutiny is drafting Albert Almora Jr. sixth overall in 2012, right before the San Diego Padres took Max Fried seventh. However, Almora hasn’t been a complete bust, as he was part of the 2016 championship team and had a couple of decent seasons, despite the fact that he has gone downhill the last couple of years and may even be non-tendered this offseason.

It’s tough to criticize draft picks, as even the best miss on some. Yet one that looks especially bad right now is Epstein’s 2017 first-round pick, when he chose Brendon Little 27th overall right before the Blue Jays took Nate Pearson 28th. While Little is barely on the Cubs’ radar right now, Pearson is one of the game’s top prospects and made his major league debut in 2020.

Chicago Cubs: Not trading Kris Bryant prior to 2020 season

At this point, we’re all getting tired of the Kris Bryant trade rumors and wish that, if a trade is going to happen, it would just happen already. With Bryant projected to make over $18 million in arbitration this year, many feel that the team needs to trade him to try to cut costs and to get something in return before he becomes a free agent.

Of course, we went through this last offseason as well. A year ago, on these pages and on many other websites, writers speculated a potential Bryant trade to seemingly every major league team. The Cubs were working within a tight budget and were looking to cut costs, but were unable to pull anything off.

Instead, the team went into 2020 with Bryant as their third baseman, and it was an injury-filled season in which Bryant performed poorly when he actually was on the field. Because of that, the Cubs’ decision to delay what may be inevitable will likely cost them a lot as part of a return package.

For example, it was rumored last offseason that the Phillies wanted Bryant. Alec Bohm, their big-time third base prospect, would have been a nice piece to get back, but he made his major league debut this year hitting .338. The thought of trading Bryant for Bohm seems almost laughable now.

Some people may say that holding Bryant down in the minors at the beginning of the 2015 season in order to reduce his major league service time would be a bad move, but I don’t think so; the team was playing by the rules and did the rational, if not moral, thing. However, a lot of people predicted that the Bryant-Cubs relationship would end badly, and it looks like that’s what’s going to happen.

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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.

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Chicago Cubs: Trading Jose Quintana for Eloy Jimenez and Dylan Cease

I still say that trading for Jose Quintana wasn’t necessarily the wrong move to make at the time back in 2017. It simply hasn’t worked out the way that we’d hoped.

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At the time of the trade with the crosstown White Sox, we knew that letting go of Eloy Jimenez and Dylan Cease was likely going to hurt later down the road. That’s not a surprise. However, the Cubs needed some starting pitching help as the team was floundering heading into the All-Star break, leading many to wonder whether the team was indeed suffering from a World Series hangover.

In Quintana, the Cubs got one of the American League’s most durable and consistent pitchers over the previous few years, though he was having a down 2017. He had a great first start for the team and did contribute in 2017, but he was up-and-down in 2018 and 2019 while missing most of 2020 due to injury. He simply hasn’t been the same pitcher that he was with the White Sox prior to the trade.

Jimenez and Cease, meanwhile, look like they will have bright careers with the White Sox, as both have reached the majors and become solid players. It sure would be nice to have them both back right now.

What really makes this trade painful is the fact that in 2017, the Cubs probably could have had Justin Verlander for next to nothing instead of Quintana. Instead, Verlander went to Houston and was tremendous for the Astros from 2017 to 2019.

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Chicago Cubs: Trading DJ LeMahieu to the Colorado Rockies

This was one of Epstein’s first moves with the club, and it turned into a disaster.

DJ LeMahieu, admittedly, wasn’t projected to be a superstar when he made his major league debut with the Cubs back in 2011. He got into 37 games that year and went 15-for-60 with no home runs. Epstein obviously didn’t think much of him, because on December 8, 2011, just weeks into the job, Epstein packaged LeMahieu and Tyler Colvin to the Colorado Rockies for Casey Weathers and Ian Stewart.

LeMahieu took a few years to come around with the Rockies, but he won a Gold Glove Award in 2014 before breaking through with the bat in 2015, batting .301 with 61 RBI while earning an NL All-Star appearance. Then, in 2016, he led the league in hitting at .348 while posting a .911 OPS. With the Yankees, he became an MVP candidate, leading the league with a 1.011 OPS in 2020. He’s a free agent this offseason and will cash in big.

Weathers never made the majors, but even that was a better ending than what happened with Stewart. The team was hoping that Stewart could be a decent third baseman for the rebuilding team in 2012; instead, he only got into 55 games and batted .201. He re-signed as a free agent prior to 2013 but was sent to the minors, which prompted Stewart to criticize the Cubs on social media. He last saw action with the Angels in 2014.

Next. Ranking Theo Epstein's five best moves with the Cubs. dark

Because it happened so early in Epstein’s tenure, some might overlook this trade compared to the one with the White Sox. However, given Epstein’s bad misjudgment of LeMahieu, this trade has to be the worst move that Epstein made.

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