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The Cubs' 10 worst trades of the 2010s

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These were not pretty.

Photo by Jonathan Daniel/Getty Images

As was the case with the bottom 10 Cubs by WAR article I wrote here last month, the purpose of this article is not to denigrate or embarrass any of the players involved. My purpose here is simply to note some trades made by the Cubs over the last 10 seasons, both by former GM Jim Hendry and by Theo Epstein’s front office, that were miscalculations or mistakes in some way, or that simply didn’t produce the value for the team that would have made them worth doing.

Some of these were just miscalculations. Others were just badly thought-out. It happens, even to smart baseball executives. And I have made a conscious decision to leave the 2016 Aroldis Chapman deal out of this discussion (and yesterday’s). Discussion of this trade has been done to death and I don’t think rehashing it is a good use of anyone’s time.

Onward!

August 18, 2010: The Cubs traded Derrek Lee to the Braves for Ty’Relle Harris, Robinson Lopez and Jeff Lorick

Here’s how I see this deal. D-Lee was approaching the end of his career at 34. His production had dropped from a very good 2009 season. And yet, at 34 he should have had more value than the three minor leaguers the Cubs got, none of whom ever played in the major leagues. In fact, only Harris ever played above A ball (and he’s still around, playing this winter in the Australian Baseball League at age 32).

Even with Lee’s decline, Hendry should have been able to get something better.

January 8, 2011: The Cubs traded Chris Archer, Robinson Chirinos, Sam Fuld, Brandon Guyer and Hak-Ju Lee to the Rays for Matt Garza, Fernando Perez and Zac Rosscup

Oh, man. This one was controversial when it was made. Hendry was desperately trying to get the Cubs back in contention after a bad 2010. I’ll admit — I thought this deal was worth it when the Cubs made it; obviously, I was wrong. Archer was the key to this one. He had several very good years under Joe Maddon and Kevin Cash in Tampa. Chirinos has become a very good player. Guyer was a useful spare part for a time. Interestingly, Lee, who was viewed as a very good prospect, flamed out in the minor leagues and never played in MLB. He was still playing last year in KBO.

At least Garza produced value for the Cubs when he was traded away two years later. That trade was covered in the companion article to this one, as it was one of the best deals of the 2010s.

One thing I will never forget about Garza’s time in Chicago was this play [VIDEO].

He was literally one easy toss to first base away from a gem, perhaps the best game of his career, and instead the ball wound up in the seats. It would have completed a three-hit shutout. But at 119 pitches, Dale Sveum lifted Garza and Shawn Camp completed the 8-0 win on April 12, 2012.

January 19, 2011: The Cubs traded Tom Gorzelanny to the Nationals for A.J. Morris, Michael Burgess and Graham Hicks

Like the D-Lee deal, this one should have brought more value. Gorzelanny had pitched reasonably well for the Cubs and had a 2.0 bWAR season in 2010.

Burgess and Hicks never played in the major leagues. Morris did, but not until five (!) years later with the Reds, and then in only seven games. The Cubs had lost him in the Rule 5 draft in 2013.

December 8, 2011: The Cubs traded DJ LeMahieu and Tyler Colvin to the Rockies for Ian Stewart and Casey Weathers

This is looking like one of the worst trades in franchise history. Theo & Co. thought Stewart, who had a couple of decent years for Colorado in 2009 and 2010, could get back to that level. LeMahieu, who had been the team’s second-round pick in 2009, was considered superfluous.

Whoops. LeMahieu has been worth 23.7 bWAR since he left the Cubs, won the N.L. batting title in 2016 and just completed a 6.0 bWAR season with the Yankees. That would have looked pretty good at second base at Wrigley Field in 2019.

Meanwhile, Stewart turned into a chronic complainer and the team suspended him for 10 days in June 2012 after he went on a rant on Twitter about his playing time. (And there’s more about that here.) I can’t reproduce the tweets here because it appears Stewart long ago deleted that account, but this was the gist, from the first of those links:

Stewart will be suspended without pay for his critical tweets of the organization that included the third baseman claiming the team “might as well release” him.

That’s exactly what they did a couple weeks later, releasing him on June 25, 2012. He signed with the Dodgers, but he never played in the big leagues for them, and then the Angels gave him 24 games in 2014 in which he hit .176/.222/.382. He last played baseball in the Nationals organization for their Triple-A team in 2015.

Just a colossal mistake by Theo & Co.

December 8, 2015: The Cubs traded Starlin Castro to the Yankees for Adam Warren and a player to be named later (Brendan Ryan)

In some ways this deal doesn’t belong here. The reason Castro was traded was that the Yankees agreed to take on $36 million of Castro’s contract, money the Cubs wanted to clear to sign Ben Zobrist to the four-year, $56 million deal he signed the same day.

I include it because the Cubs never intended for Ryan to be on the team at all. They released him two weeks later.

And Warren was just awful for the Cubs. He never seemed to want to be here, and the Cubs couldn’t really find the right role for him. Eventually he was sent back to the Yankees in the Aroldis Chapman trade.

So the Cubs did get some value in this trade, but the deal on its face didn’t provide much.

December 7, 2016: The Cubs traded Jorge Soler to Royals for Wade Davis

Had the Cubs won the 2017 World Series, this deal wouldn’t be in this article. But they didn’t. Davis had a decent year (1.9 bWAR) for the Cubs and then left as a free agent, signing a four-year contract with the Rockies. He’s been pretty bad there.

Soler, as he had in Chicago, spent his first two years in Kansas City fighting several injuries. Finally healthy in 2019, he hit .265/.354/.569 with 48 home runs, leading the A.L. in homers and setting a Royals franchise record. He turns 28 in February and could be a good player for K.C. for several years to come.

If healthy, of course.

July 13, 2017: The Cubs traded Eloy Jimenez, Dylan Cease, Bryant Flete and Matt Rose to the White Sox for Jose Quintana

I’ll just repeat what I said above re: the Soler/Davis deal: If the Cubs had won the 2017 World Series, this deal would have been worth it.

But they didn’t. I have defended this trade in the past, as Quintana had been a reasonably productive starter in 2017 and 2018. He was also having a decent 2019 until a horrendous September (five starts, 11.09 ERA, 2.250 WHIP) pushed his season numbers into the dumpster.

Q has been worth 4.6 bWAR in 2½ seasons as a Cub. That’s not awful, but we had hoped for more. Flete and Rose both played in indy ball in 2019 and are likely never going to be big leaguers, so this deal is essentially Jimenez and Cease for Quintana.

The Cubs picked up Quintana’s 2020 option for $10.5 million. It’s entirely possible he gets traded this winter, which would bring other players into the mix of evaluating this trade in the long term. But for now, even if Cease and Jimenez are just average MLB regulars and not stars, this deal has tilted in the White Sox’ favor.

July 31, 2017: The Cubs traded Jeimer Candelario, Isaac Paredes and cash to the Tigers for Alex Avila and Justin Wilson

Theo & Co. were quite busy in the summer of 2017 trying to squeeze out another World Series title. It didn’t work. Avila was competent for the Cubs, then left via free agency for the Diamondbacks, for whom he was mediocre for two years. Wilson was awful in 2017 for the Cubs, better in 2018, then left in free agency for the Mets.

Meanwhile, Candelario has been a decent player for a really bad Tigers team. The key here, though, might be Paredes. He’s only 20 and hit .282./368/.416 in Double-A in 2019, and MLB Pipeline ranks him the Tigers’ fifth-best prospect. A few years down the road, Paredes could make the Cubs really regret this trade.

November 29, 2018: The Cubs traded Tommy La Stella to the Angels for Conor Lillis-White

Bad, bad, bad.

That’s what this trade was.

TLS was a useful bench player for the Cubs in 2018. He had 25 pinch-hits, a Cubs franchise record and just two short of the MLB record.

He’d certainly have looked much better in a Cubs uniform in 2019 than Daniel Descalso. La Stella was having an outstanding season and had been named to the A.L. All-Star team when he suffered a broken leg and missed the rest of the season.

Lillis-White has yet to pitch in the Cubs organization. He was injured and missed the entire 2019 season.

July 15, 2019: The Cubs traded Mike Montgomery to the Royals for Martin Maldonado

It’s not that the Cubs shouldn’t have traded Montgomery. He was clearly unhappy in his half-relief/part-time starter role and wanted to be a rotation starter. There was no room for him to do that in Chicago. But the Cubs probably should have traded him last offseason, because in 2019 he was injured and didn’t throw well when healthy, decreasing his trade value.

The Cubs had supposedly been after Maldonado in the 2018-19 offseason as a backup (Victor Caratini then would have then played most of the year at Iowa), but he wanted to be a starter, so he signed with the Royals for $2.5 million — after reportedly turning down a two-year, $12 million offer from the Astros, after which he fired Scott Boras as his agent.

Maldonado played in just four games for the Cubs, going 0-for-11. He complained about his lack of playing time, so the Cubs got him to the Astros after all, for Tony Kemp, on July 31.

Three days later Willson Contreras suffered a hamstring injury. Maldonado would have gotten a lot more playing time after that. He hit .202/.316/.464 with six home runs in 27 games for Houston.

And the Cubs have Tony Kemp to show for Mike Montgomery.

Poll

Which trade was the Cubs’ worst of the 2010s?

This poll is closed

  • 1%
    August 18, 2010: The Cubs traded Derrek Lee to the Braves for Ty’Relle Harris, Robinson Lopez and Jeff Lorick
    (25 votes)
  • 10%
    January 8, 2011: The Cubs traded Chris Archer, Robinson Chirinos, Sam Fuld, Brandon Guyer and Hak-Ju Lee to the Rays for Matt Garza, Fernando Perez and Zac Rosscup
    (216 votes)
  • 0%
    January 19, 2011: The Cubs traded Tom Gorzelanny to the Nationals for A.J. Morris, Michael Burgess and Graham Hicks
    (4 votes)
  • 47%
    December 8, 2011: The Cubs traded DJ LeMahieu and Tyler Colvin to the Rockies for Ian Stewart and Casey Weathers
    (931 votes)
  • 1%
    December 8, 2015: The Cubs traded Starlin Castro to the Yankees for Adam Warren and a player to be named later (Brendan Ryan)
    (22 votes)
  • 3%
    December 7, 2016: The Cubs traded Jorge Soler to Royals for Wade Davis
    (66 votes)
  • 28%
    July 13, 2017: The Cubs traded Eloy Jimenez, Dylan Cease, Bryant Flete and Matt Rose to the White Sox for Jose Quintana
    (565 votes)
  • 1%
    July 31, 2017: The Cubs traded Jeimer Candelario, Isaac Paredes and cash to the Tigers for Alex Avila and Justin Wilson
    (20 votes)
  • 5%
    November 29, 2018: The Cubs traded Tommy La Stella to the Angels for Conor Lillis-White
    (114 votes)
  • 0%
    July 15, 2019: The Cubs traded Mike Montgomery to the Royals for Martin Maldonado
    (16 votes)
1979 votes total Vote Now