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The Cubs’ 10 best trades of the 2010s

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Theo & Co. have traded very, very well.

Photo by Jamie Sabau/Getty Images

This article was first conceived as “The Cubs’ 10 best transactions of the 2010s,” which would have included free-agent signings, draft picks, etc.

But I decided to narrow it down to trades, in no small part because Theo Epstein’s front office has been very, very good at them.

Having said that, you’ll see that the best of these are four years gone. More recently, the trading magic has diminished somewhat.

These deals are listed in chronological order, not by WAR or any other statistical measure. To some extent they rely on my own opinion rather than analytics, though I don’t think you’ll find any egregious omissions, save one.

I’ve decided to leave out the deal in which the Cubs acquired Aroldis Chapman. This is because there are some who will say “They won the World Series!”, to which the response is generally, “But they gave up Gleyber Torres!” Personally, I’m on the “won the World Series” side of that conversation, though I can understand the other view. I didn’t think the discussion here would have been furthered by including it, so it’s out.

Oh, and in case you were wondering: Yes, there will be a companion “worst deals” article, tomorrow.

December 23, 2011: The Cubs traded Sean Marshall to the Reds for Dave Sappelt, Ronald Torreyes and Travis Wood

Wood put together some pretty good years on the North Side, with an All-Star appearance included, and helped the team with his bat as well. Between pitching and hitting he was worth 7.3 bWAR in his time with the Cubs, and then there was this [VIDEO].

And this:

Dennis Wierzbicki-USA TODAY Sports

All worth it. FWIW, Marshall was injured and pitched in just 31 games for the Reds.

The Cubs should probably have not let Torreyes go, or kept him when they briefly reacquired him last winter, but that’s a story for another day.

January 6, 2012: The Cubs traded Andrew Cashner and Kyung-Min Na to the Padres for Anthony Rizzo and Zach Cates

This was a risk, of sorts: Cashner was seen as perhaps a high-end starter or closer and Rizzo had struggled in his brief time in the majors for the Padres in 2011.

Eight years later, Rizzo is one of the most beloved Cubs of the current era and maybe ever, has been worth 33 bWAR as a Cub and might someday get his number on a flag atop Wrigley Field. Cashner is on his fourth team since leaving the Padres and since he left the Cubs: 10.5 bWAR. Neither Cates nor Na ever played in the major leagues.

July 31, 2012: The Cubs traded Ryan Dempster to the Rangers for Kyle Hendricks and Christian Villanueva

We should all be thankful that Dempster invoked his 10-and-5 rights to reject a trade to the Braves that would have brought Randall Delgado to Chicago. Delgado was very highly regarded midsummer 2012 and Hendricks had yet to pitch above A ball.

The rest, as they say, is history. Kyle Hendricks has a chance to be one of the best pitchers in Cubs franchise history — 20.6 bWAR and counting — and Dempster retired after getting himself a World Series ring with the 2013 Red Sox, so it worked out for Demp, not so much for the Rangers, who got two mediocre months from him and nothing when he departed as a free agent.

July 2, 2013: The Cubs traded Steve Clevenger and Scott Feldman to the Orioles for Jake Arrieta, Pedro Strop and cash

This is not only one of the best deals of the 2010s for the Cubs, it’s one of the best in franchise history. It would have been a good deal if the Cubs had only gotten Strop for Clevenger and Feldman, but acquiring Arrieta was a masterstroke of scouting. He’d been awful for the Orioles in 2013 but Cubs scouts thought he could be fixed. They were right, and then some. A Cy Young Award, two no-hitters and 20.1 bWAR in four and a half seasons. Strop has 7.4 bWAR as a Cub and could be back again in 2020.

Feldman made 15 mediocre starts for Baltimore (0.6 bWAR) and left as a free agent. Clevenger posted 0.2 bWAR in parts of three seasons for the Orioles.

Oh, and the Cubs got a compensation draft pick when Arrieta rejected a 2017 qualifying offer and left as a free agent. That pick was Cole Roederer, who’s one of the Cubs’ better outfield prospects.

July 22, 2013: The Cubs traded Matt Garza to the Rangers for Carl Edwards Jr., Justin Grimm, Mike Olt and Neil Ramirez

There were a lot of complaints when Jim Hendry traded away a bunch of players for Garza in 2011. I’ll admit I thought the deal was OK at the time, but that turned out to be wrong. One of the players sent away in that deal, Robinson Chirinos, was never much of a prospect with the Cubs but has blossomed into a fine MLB catcher over the last three years.

The Cubs did get value in return when Theo sent Garza away in 2013 (and Garza produced 5.8 bWAR as a Cub, and negative bWAR after he left). Edwards and Grimm both put together good seasons for Cubs playoff teams. Ramirez had his moments, but could not stay healthy. Olt was the only bust from this deal.

You’ll never forget this, right?

David Richard-USA TODAY Sports

The Cubs might still get some value from this trade going forward, as Edwards was sent to the Padres for Brad Wieck last summer. Wieck threw pretty well for the Cubs down the stretch and the team hopes he’ll be a big part of the bullpen in 2020.

July 31, 2014: The Cubs traded Emilio Bonifacio, James Russell and cash to the Braves for Victor Caratini

This one flew under the radar for a while, but what a smart deal this turned out to be. Caratini has become one of the best backup catchers in baseball, with a 1.3 bWAR season in 2019. He could start for a lot of teams.

Russell threw fairly well for the Braves. He left as a free agent, returned to the Cubs but wasn’t all that good in 2015, and his last MLB experience was seven games for the 2016 Phillies.

Bonifacio hung on through 2017 with the Braves and White Sox, posting -2.0 bWAR for those teams.

November 16, 2014: The Cubs traded Arodys Vizcaino to the Braves for Tommy La Stella

All I’ll say is that this deal would look a lot better if the Cubs had kept TLS. More on this in the companion article tomorrow.

December 9, 2014: The Cubs traded Zack Godley and Jeferson Mejia to the Diamondbacks for Miguel Montero

Miguel Montero had one good year as a Cub, one as a somewhat unwilling backup, and left the team under less-than-ideal circumstances.

But you will never forget this hit [VIDEO].

And this was pretty important, too. [VIDEO]

Those were the only hits Montero had in the 2016 postseason, both critical to the World Series win. So this trade produced excellent value, and Mejia had himself been a trade acquisition, for Tony Campana in February 2013.

Incidentally, Godley, who had a couple of decent years for the Diamondbacks, regressed in recent years and was released by the Blue Jays last September. He might be worth a minor-league invite to Cubs spring training in 2020.

January 19, 2015: The Cubs traded Dan Straily and Luis Valbuena to Astros for Dexter Fowler

The importance of this deal cannot be overstated. The Cubs got a 3.7 bWAR season from Fowler in 2015, and he helped them make the postseason with a .350 OBP out of the leadoff spot. And then, just when it appeared he had signed with the Orioles in February 2016, he made a surprise appearance at spring training:

Fowler was even better in 2016, posting a .393 OBP leading off, completing a 4.0 bWAR season and creating a Joe Maddon slogan: “You go, we go.”

The Cubs have struggled to find a competent leadoff hitter since Fowler departed. Note, I am not suggesting they should have paid Dex what he got from the Cardinals (five years, $82.5 million), only that they haven’t done a good job identifying a successor.

November 20, 2018: The Cubs traded Jason Vosler to the Padres for Rowan Wick

You’ll note that there are more than three years in between the trade above and this one. Theo Epstein’s trade magic produced several important players for the Cubs’ World Series run. Since then? Not so much.

This deal could be useful for several years to come. Wick, a converted catcher, had struggled in the San Diego system. The Cubs got him turned around and he became a useful setup man, a role in which he’ll continue in 2020. He just turned 27.

Meanwhile, Vosler, a third baseman who was (obviously) blocked in the Cubs system, has still not played in the big leagues.

Poll

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

This poll is closed

  • 0%
    December 23, 2011: The Cubs traded Sean Marshall to the Reds for Dave Sappelt, Ronald Torreyes and Travis Wood
    (2 votes)
  • 34%
    January 6, 2012: The Cubs traded Andrew Cashner and Kyung-Min Na to the Padres for Anthony Rizzo and Zach Cates
    (451 votes)
  • 3%
    July 31, 2012: The Cubs traded Ryan Dempster to the Rangers for Kyle Hendricks and Christian Villanueva
    (47 votes)
  • 58%
    July 2, 2013: The Cubs traded Steve Clevenger and Scott Feldman to the Orioles for Jake Arrieta, Pedro Strop and cash
    (764 votes)
  • 0%
    July 22, 2013: The Cubs traded Matt Garza to the Rangers for Carl Edwards Jr., Justin Grimm, Mike Olt and Neil Ramirez
    (0 votes)
  • 0%
    July 31, 2014: The Cubs traded Emilio Bonifacio, James Russell and cash to the Braves for Victor Caratini
    (1 vote)
  • 0%
    November 16, 2014: The Cubs traded Arodys Vizcaino to the Braves for Tommy La Stella
    (3 votes)
  • 0%
    December 9, 2014: The Cubs traded Zack Godley and Jeferson Mejia to the Diamondbacks for Miguel Montero
    (1 vote)
  • 1%
    January 19, 2015: The Cubs traded Dan Straily and Luis Valbuena to Astros for Dexter Fowler
    (23 votes)
  • 0%
    November 20, 2018: The Cubs traded Jason Vosler to the Padres for Rowan Wick
    (6 votes)
1298 votes total Vote Now