Theo Epstein Has Proved To Be A Trade Magician

When Theo Epstein became Chicago’s President of Baseball Operations in 2011, he was inheriting a team that needed a full rebuild from the ground up. Coming off three straight losing seasons the Cubs front office went to work not only improving the farm system but systematically improving the big league club as well.

The Cubs have built up to the team we see today in a variety of ways. Through the draft and the international market, Chicago has been able to land Wilson Contreras, Javier Baez, Kyle Schwarber, and Kris Bryant. The team has also been active in free agency by adding Jason Heyward, Jon Lester, Ben Zobrist, John Lackey, and David Ross.

However, when evaluating Theo Epstein and his roster construction there has been one method he has excelled at. He has consistently made shrewd trades to help perfect the World Series winning roster we see today.

Below are some of Epstein’s most impactful trades during his tenure as the Cubs President.

Honorable Mentions:

RHP Kyle Hendricks and INF Christian Villanueva from Rangers for RHP Ryan Dempster

When Theo Epstein first looked to move Dempster, the Atlanta Braves were the preferred trading partner at the time. However, Dempster had other ideas and vetoed the trade. The Cubs finally settled on the Rangers and shipped Dempster off to Texas for Christian Villanueva and then unheard of pitching prospect Kyle Hendricks. Since then Hendricks has cemented himself as the No. 3 starter and was a 2016 NL Cy Young Award contender.

RHPs Justin Grimm, Carl Edwards Jr., 3B Mike Olt, RHP Neil Ramirez from Rangers for SP Matt Garza

On July 22, 2013, the Cubs sent Matt Garza to the then contending Rangers in a multi-player blockbuster. While Mike Olt and Neil Ramirez never blossomed into impactful members of the Cubs, the other two players involved have proven to be important contributors to the bullpen.

Justin Grimm has been streaky so far in his career with the Cubs, but when he is on, he is one of the more difficult relievers to go against. Carl Edwards also known as “The String Bean Slinger” has been fantastic. Over three seasons he sports a 2.80 ERA, 12.59 strikeouts per nine innings, and a 1.1 WAR. He’s only 25 years old and has the potential to become a shutdown closer in the future.

LHP Aroldis Chapman from Yankees for SS Gleyber Torres, OF Billy McKinney, and RHP Adam Warren

This one may surprise some people as an honorable mention. The Cubs did have to part ways with some significant prospects in order to land Chapman. Apart from Adam Warren, the Cubs threw in Billy McKinney and Gleyber Torres, the latter now the No. 2 prospect in the Yankees system. It worked out in the end for the Cubs as Chapman was dominant throughout the playoffs was one of the main reasons why the Cubs ended their World Series drought.

The Top Five:

5. CF Dexter Fowler from Astros for RHP Dan Straily, INF Luis Valbuena

When Chicago acquired Fowler, they were in desperate need of a leadoff hitter and a center fielder. Luckily for the Cubs Fowler filled both roles and only cost a minor league pitcher and an infielder with no clear path to Wrigley. After his first season in which he vastly improved the defense in centerfield and the offense at the leadoff position, Fowler returned on a one-year deal. His second season was even better than the first. After all, he was the first player to hit a leadoff home run in Game Seven of the World Series.

4. LHP Mike Montgomery and RHP Jordan Pries from Mariners for 1B Dan Vogelbach and RHP Paul Blackburn

The trade for Mike Montgomery was another case of Epstein trading from a position of strength to bolster a weakness in the Cubs lineup. Dan Vogelbach while an impressive hitter was buried on the Cubs infield depth chart. Mike Montgomery became a very important member of the Cubs bullpen throughout the 2016 playoffs. Pitching 14 ⅓ innings, with a 3.14 ERA including being on the mound for the last out of Game Seven against the Indians.

3. RHPs Jake Arrieta and Pedro Strop from Orioles for C Steve Clevenger and RHP Scott Feldman

With this trade, we start to see some of Epstein’s wizardry in the trading world. The Cubs sent a rental pitcher in Scott Feldman and backup catcher Steve Clevenger for RHPs Pedro Strop and Jake Arrieta.

Strop has been a solid addition for the bullpen with a 2.77 ERA while amassing 235 strikeouts. However, Jake Arrieta was the steal of this trade. Once he got the chance to work with pitching coach Chris Bosio he has turned himself into a top-level starter. He has over 600 strikeouts and a 3.10 ERA over the course of five seasons with the Cubs. During 2015 he had one of the best seasons ever with 22 wins and a ridiculous 1.77 ERA while taking home the NL Cy Young Award.

2. SS Addison Russell, OF Billy McKinney, RHP Dan Straily from Athletics for RHPs Jeff Samardzija and Jason Hammel

Theo Epstein pulled off one of his most audacious trades in 2014 when he sent the top two starters at the time in Jeff Samardzija and Jason Hammel to Oakland in exchange for Billy McKinney, Dan Straily, and Addison Russell. While Straily and McKinney didn’t directly produce for the Cubs, they were both used in other Cubs trades that helped build the Cubs roster.

Addison Russell was the crown jewel of this trade. At the time he was one of the top prospects in all of baseball. With his gold glove worthy defense he quickly became the starting shortstop and has gotten better each season including an All-Star selection in 2016. If his hitting can catch up to his defense then the Cubs just might have one of the truly elite shortstops in the game.

1. 1B Anthony Rizzo, RHP Zach Cates from Padres for RHP Andrew Cashner, OF Kyung-Min Na

After only a few months as the new Cubs President of Baseball Operations, Theo Epstein went after a prospect he and the rest of the front office were familiar with from their time with Boston. The Cubs acquired the first franchise cornerstone in Anthony Rizzo for a hard-throwing Andrew Cashner.

At the time of the deal, some Cubs fans were leery of letting go of a pitcher with upper 90’s velocity, but the deal couldn’t have worked out better for the Cubs. Anthony Rizzo has become one of the best first basemen in the game. During his first six seasons with the Cubs, he has posted an impressive .860 OPS, 146 Home Runs, a 21.6 WAR, and took home his first Gold Glove in 2016. Rizzo is only 27 years old and on a very team-friendly deal for the next two years, it’s hard to imagine Theo topping this deal anytime soon.

Looking Like Another Win:

RHP Wade Davis from Royals for OF Jorge Soler

When the Cubs acquired Aroldis Chapman, it was clear that he was going to be nothing more than a rental. That meant Epstein would have to find another viable replacement during the offseason to ensure the Cubs maintained their stellar bullpen. Well, it would appear Theo did just that by stealing Wade Davis from the Royals in exchange for Jorge Soler.

Jorge Soler was a fan favorite by many and had shown plenty of flashes in during his young career as a Cub. He had a ridiculous postseason in 2015 posting an impressive .474 BA, and a 1.705 OPS. However, these flashes were intermittent and when he wasn’t dominating he was often injured and unable to contribute.

Since Wade Davis has come over he has been flat out dominant for the Cubs. He has converted all 13 save opportunities while only allowing four runs, with just three of them being earned. He has posted 31 strikeouts in 22.1 innings pitched. One thing’s for certain if he maintains this throughout the second half and into the playoffs, the Cubs will once again have a dominant closer to shut down opposing teams.

As the 2017 trade deadline approaches be on the lookout for Theo Epstein and the rest of the Cubs front office to strike gold again.