Theo the Trader: Evaluating Epstein’s Trades During His Cubs Tenure

There was a time when baseball fans joked, “Why would anyone ever work a deal with Billy Beane? Beane wins every time.”

In evaluating Theo Epstein’s performance as an exchanger of talent on the Cubs behalf, the same question holds true. For every significant Cubs trade transaction in which Epstein has been involved, it seems that he has come out not just ahead, but as the undisputed victor.

In an effort to evaluate Epstein’s trade decisions, I have broken the transactions since November 2011 into four categories: “Relatively Insignificant,” “Cut Your Losses,” “Empire Builders,” and “You Can’t Win Them All.

Certainly there have been some lesser deals where it’s impossible to declare a winner. Sometimes, the intent was to clear salary, clear a positional logjam, or to supplement organizational depth. They were low-risk, low-return moves, and have not turned out to be noteworthy in either direction thus far. I would put the following trades into this “Relatively Insignificant” category:

  • Aaron Kurcz/Chris Carpenter to Boston for Jair Bogaerts
  • Marlon Byrd/Cash to Boston for Michael Bowden and Hunter Cervenka
  • Geovany Soto To Texas Rangers for Jake Brigham
  • Jeff Baker to Detroit for Marcelo Carreno and cash
  • Blake Lalli to Oakland for Anthony Recker
  • Tony Campana to Arizona for Jesus Castillo and Erick Leal
  • Ian Dickson to Washington for Henry Rodriguez (not that one)
  • Darwin Barney to the Dodgers for Jonathan Martinez
  • Marco Hernandez to Boston for Felix Dubront
  • Jose Arias/Tyler Bremer to Miami for Jacob Turner
  • Brian Bogusevic to Miami for Justin Ruggiano
  • Ruggiano to Seattle for Matt Brazis
  • Mike Kickham to Seattle for Lars Huijer
  • Rafael Lopez to Los Angeles Angels of Anaheim for Miguel Rondon
  • PTBNL to Seattle for Fernando Rodney

Marlon Byrd, Geovany Soto, Jeff Baker, Darwin Barney, and Justin Ruggiano were all traded to clear positions for developmental players while saving some money and bringing in some low-impact prospects, none of which appear all that promising at this point.

As for the cost, of the 10 minor-league players the Cubs sent away in these deals, four are out of baseball, two are still in A-ball at age 24, and the rest have combined for a total of zero games played in the big leagues. In fact, only one player, (Marco Hernandez) could even be considered a prospect at this point in his career (.298/.321/.444 between Double- and Triple-A this season). In short, these moves probably helped a little, but certainly haven’t hurt at all.

There have also been several trades made where improving the team’s on-field performance for that season was not the goal. Large contracts, inherited from the previous administration needed to be moved to turn over the team’s leadership, save money, and assist the team in acquiring a better draft pick through the process of…not winning.

To accomplish these goals, Epstein and company executed the following “Cut your losses” trades:

  • Carlos Zambrano to Miami for Chris Volstad
  • Carlos Marmol and cash to the Dodgers for Matt Guerrier
  • Alfonso Soriano to Yankees for Corey Black

Each of these trades sent a high-profile, highly compensated veteran packing. Zambrano had worn out his welcome and had become largely ineffective. Marmol was unable to close games and had lost the devastating slider with which he had once put hitters out of their misery. Soriano was still performing adequately, but was never going to be a part of the team when they were ready to contend. Additionally, his home runs were expensive financially, but also costly in positive wins added—the Cubs were not exactly trying to pad their win stats during this period.

All three trades required that the Cubs send significant amounts of cash with the players to induce the acquiring team to accept the player and his respective contractual absurdities.

Soriano played just about to his career averages for half a season in New York, then retired midway through the following season. Neither Zambrano nor Marmol were ever effective pitchers again, and both were out of baseball in short order. Trading these players signaled explicitly that the Cubs were in full-fledged rebuilding mode. Epstein unloaded as much of the contracts as he could and moved on. With the old guard gone, it was time to reload.

In order to build an organization that will sustain itself independent of free agency, the Cubs decided the quickest route—and one of highest probability—was for the team to lose a lot for a long time in order to acquire top draft picks. Then, they needed to expertly evaluate, project, and draft talent. To speed the process of building a winner, it helps if you can flip some “win-now guys” to a team looking to win now while you, yourself, are looking to win later. If done properly, the rebuilding GM can lower his team’s chance of winning (thereby bettering their draft position), while convincing a team who believes they are close to a World Series roster into parting with players that they would never consider trading normally. I consider the following trades to be trades of this type. I call them “Empire Builders”:

  • Kyung-Min Na and Andrew Cashner to San Diego for Anthony Rizzo and Zach Cates
  • Sean Marshall to Cincinnati for Ronald Torreyes, Dave Sappelt, and Travis Wood
  • Ryan Dempster to Texas for Christian Villanueva and Kyle Hendricks
  • Steve Clevenger and Scott Feldman to Baltimore for Jake Arrieta, Pedro Strop and Cash
  • Matt Garza to Texas for Carl Edwards Jr., Justin Grimm, Mike Olt, and Neil Ramirez
  • Jeff Samardzjia and Jason Hammel to Oakland for Addison Russell, Billy McKinney, Dan Straily, and Cash
  • Zach Godley and Jefferson Mejia to Arizona for Miguel Montero #wearegood

Honestly, it is hard to even write about some of these deals without chuckling at how one-sided they are, but they actually happened, and history (and statistics) have determined Epstein and the Cubs front office to have won each of them by knockout. The talent received in these trades makes up a large part of the core of the Cubs future, and the player traded away was not expected to play any role when the Cubs were ready to compete.

Each of the established players traded away by the Cubs in these deals was dealt at the peak of their value, and Epstein seems to have extracted maximum value for each of them. Paired with the impeccable early round drafting of the Epstein era, the Cubs are now stocked with an array of talent that would be difficult for any organization to match from top to bottom.

The lone trade above that doesn’t fit perfectly into this category is Cashner for Rizzo. At the time of the trade, both were young players whose prospect status had recently expired. The Cubs, as has been their tendency, bet on the position player in Rizzo, likely believing that Cashner was either headed for a career in the bullpen or as a starter with frequent trips to the DL. And while Cashner has stuck as a starter and remained healthy for 2015, it’s hard to argue that the Cubs haven’t come away victors with their acquisition of Rizzo. The young first baseman was signed to a team-friendly extension over two years ago, has blown past his perceived ceiling due to elite work ethic and makeup, and has become the face and leader of a young team that appears headed to its first of many trips to the postseason.

Add in the acquisition of Cy Young candidate Arrieta and the blossoming Russel and one wonders, why, then, would any team engage with the Cubs in significant trade talks with recent history pointing to an unpleasant result? Well, there have been a few missteps along the way:

You Can’t Win Them All


  • Tyler Colvin and D.J. LeMahieu to Colorado for Casey Weathers and Ian Stewart
  • Wellington Castillo to Seattle for Yoervis Medina

I’m certainly splitting hairs here, because the only trade that really went badly was Colvin/LeMahieu for Ian Stewart. Colvin hasn’t been a significant loss, but LeMahieu has been an All-Star and a Gold Glover at second base for Colorado. The Cubs wouldn’t have an easy place for him to play with their depth of middle infield talent, but the return on the trade (Ian Stewart) was so negligible that it makes the trade look worse.

Castillo had to go because the team has an over-abundance of catchers, and Castillo doesn’t frame pitches well. I list this trade as a loser simply because I think there could have been more value to be had for Castillo if he had been moved prior to the Cubs acquiring Miguel Montero and David Ross or even perhaps later in the season.

I imagine that every general manager/team president has a trade they wish they could take back. If Epstein’s largest regret to this point is that he let D.J. LeMahieu get away, I would think he can live with that mistake.

Through a combination of superior talent evaluation, realistic assessment of the team’s trajectory, and top-notch talent development, Epstein and his staff have turned a talent deficient organization into a looming juggernaut, filled with organization-changing talent that is the envy of most clubs. The challenge changes, though, from this point forward, and it will be interesting to see how well Epstein and company adapt. It’s easier to be sellers—you set your price high and wait for a buyer to come to you. It’s much more difficult to be the buyer—to be in charge of the team in contention.

The Cubs have shown much restraint this year in making only minor moves even though the team is contending. It would have been easy to justify selling out for a big-time starter with years of control left such as Cole Hamels, but they resisted. It is logical to assume that Epstein is reluctant to part with the elite talent he so carefully collected when he can fill the need for a top-of-the-rotation starter in the offseason for cash only. After this season, though, fans’ expectations will change when they feel the team should be going “all-in.” Epstein will need a well-formed strategy and will need to cling to it above all. Identify the parts that are expendable and stay within your plan.

If this front office has proven anything beyond any doubt to this point, it is that they are extremely patient and disciplined. Time will be the ultimate judge of the effectiveness of all future moves—both executed and declined. Ultimately, the best measuring stick will be the number of World Series Championships on display at Wrigley Field.

Lead photo courtesy of Kyle Terada-USA TODAY Sports

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15 comments on “Theo the Trader: Evaluating Epstein’s Trades During His Cubs Tenure”


“Each of the established players traded away by the Cubs in these deals was dealt at the peak of their value”

Yeah…you definitely can’t say this about Matt Garza. At all. They waited a year and a half too long on him. They did great for a half season of him, but they would have gotten back significantly more trading away two years of a guy coming off of a ~5 win season

Jeff Lamb

I debated internally how to word this. I meant to say that none of the players referenced ever had a higher value after they were traded away by Theo. Your point is valid.


You forgot Luis Valbuena for Dexter Fowler.

Jeff Lamb

I certainly did. I had a graph written on it, and somehow didn’t include it. My mistake completely. Good catch.


I know Godley didn’t fair well against us, but I don’t think we can call the Godley for Miggy trade a success yet. It may turn out to be a flop depending on Godley.

Jeff Lamb

Your point has merit, but the contributions Montero has made both offensively and towards the success of the pitching staff make this a win in my opinion. If Godley turns out to be Jake Arrieta, we will have to revisit.


nice article!

Was also thinking Fowler as well as a win, considering that valbuena was a waiver pickup.

wanted to add some other trades I was thinking of:
Hairston for Pineyro who eventually became Haren (just shutting down the Cards for 1 game is a win)
the LaStella trade is looking like a loss right now as there’s no middle infield room and Vizcaino would look good in the pen right now

Jeff Lamb

You’re definitely right about Fowler.
I had the Haren trade as a loss for the Cubs, but in consultation with our editorial staff, we decided this one was too soon to tell.


I’m curious what people’s thoughts are on Vizcaino. The stats have been impressive in the recent going, but I am not sure if he is considered part of their plans once 2017 rolls around.

Obviously, things like LaStella’s injury are going to happen, but it would have been great if he had been more of a bridge in the middle infield. In hindsight, the timing of the acquisition looks curious, but more than anything else, this was bad luck.

Tim M

Good article. Really puts the Theo regime’s work in perspective. Hard to believe, but in a few short years the Theo org has already made three trades IMO that might go down in the books as three of the greatest trades in franchise history. I don’t think that’s much of a stretch considering these trades: Rizzo for Cashner, Russell/McKinney for Shark and Hammel, and Arrieta for Feldman/Clevenger. That last one still makes me chuckle.

Dan Rivera

Theo has done a remarkable job assembling this ballclub. Its amazing that Joe Maddon has been able to get so much out of players that are so young. As a Cub fan, I am not really used to seeing a organization that others admire from afar. As a result I was very skeptical that this would work and thought that the Cubs would take 2 yrs to become a elite team. Boy was I wrong.

Talent for talent, I feel that the Cubs can match up with anyone right now.

jan labij

I do not think the trade of the second baseman was a real loss from the Cubs point of view. Even now. Or maybe especially now. His career trajectory was estimated to be wrong for the Cubs re-building process. Now Theo & co. could be wrong about this in the sense that the Cubs have become a contender a year ahead of expectations, but second base problems have not been very much in evidence so far. Trading for LaStella was not a foolish move either. The reason it now looks not so good is because we have four other guys able play second base and hit better than LaStella. Coghlan was much better at second than I ever thought he would be. Russell was very good at second. Castro plays better at second than he does at short. And then there is that guy who had so much fun hitting a home run the other day, he felt compelled to take a bow-with Rizzo egging him on.

Brad Hacker

Great article Jeff – well done. Although this wasn’t a Theo regime trade, it’s can’t be overstated how big the hiring of Joe Maddon was…this is also a very big reason for there success this year.

Brad Hacker

Sorry… “…it can’t” and “…their…” not “…there…” .

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