Theo Epstein Is Good At Trading Top Prospects

Will Gleyber Torres be good? Let’s ask Theo.

As many of you know by now, the Cubs acquired Aroldis Chapman from the Yankees for Adam Warren and prospects Gleyber Torres, Billy McKinney, and Rashad Crawford. The main prize for the Yankees is Torres, a 19 year-old single-A shortstop who was ranked the 24th overall prospect by

The point of this article isn’t to decide which team “won” or “lost” the trade (I think both teams “won”), but instead to look at the track record of trading top prospects, like Torres, of Cubs’ President of Baseball Operations– Theo Epstein. Epstein is widely regarded as one of the best in the business of baseball team-assembling. What he has done with the Cubs organization since taking over in 2012 is really really special. Since the Cubs have been in rebuilding-mode for most of Epstein’s tenure, there hasn’t been a whole lot of trading away top prospects for bonafide superstars. The Torres-Chapman deal changes this. So, over is whole career, how has Theo been at trading away top prospects? Well, he’s been pretty good at it. Let’s take a look.

For the sake of this exercise, I’ve defined “top prospect” as being ranked in the top 3 of the organization’s prospects list. You’ll see the highest ranking that the prospect reached in parentheses.

  • July 2003: Sent Freddy Sanchez (1*) to Pittsburgh for Brandon Lyon and Jeff Suppan

This is actually one that Theo would probably like to have back. Sanchez went on to hit .334/.378/.473 for the Pirates in 2006– his best year as a pro. Over his career, Sanchez was a three-time all-star and accumulated 15.7 WAR. Meanwhile, Lyon only lasted until the end of the season in Boston as a middle-reliver (4.12 ERA in 59 IP) before being part of the Curt Schilling trade (more on that later). Suppan was even worse– compiling a 5.57 ERA in 10 starts before the Sox let him go via free agency.

  • November 2003: Sent Jorge de la Rosa (1) to Arizona for Curt Schilling

De La Rosa went on to have fine career, most notably with the Rockies, but he’s a former #1 prospect with a 4.62 ERA over 13 seasons– not exactly ideal. Schilling, obviously, was an integral part of Boston’s 2004 World Series team. I’d chalk this one up as a win for Theo.

  • November 2005: Sent Hanley Ramirez (1) and Anibal Sanchez (3) to Florida for Josh Beckett and Mike Lowell

Statistically speaking, this one might be a wash. Hanley went on the win rookie-of-the-year for the Marlins in 2006, and had compiled 40.1 WAR before returning to the Red Sox. Sanchez went on to have some fine seasons with the Marlins before blossoming into a star with the Tigers– he had a league-leading 2.57 ERA and 162 ERA+ (league-average ERA was 62% higher) in 2013. Beckett won 20 games and had a league-leading 3.08 FIP in 2007. Lowell hit .290/.346/.468 in five seasons with the Sox– which was a nice surprise for a guy acquired in his thirties. Undoubtedly, teams acquire players with the end-goal of winning a World Series. Did Ramirez and Sanchez help lead the Marlins to a championship? No. Did Beckett and Lowell help the Red Sox do the same? Yes. Theo wins again.

  • January 2006: Sent Kelly Shoppach (3) to Cleveland for Coco Crisp

Thought of as as an above-average backup catcher, Shoppach hit 26 homeruns in AAA in 2005, and was then flipped for Crisp. He went on to hit 70 homeruns over 9 MLB seasons while hitting .223/.312/.413. Not exactly above-average, even for a backup. Crisp didn’t exactly live up to the hype either, but was part of the 07′ World Series team.

  • July 2008: Sent Brandon Moss (2) and Craig Hansen (2) to Pittsburgh for Jason Bay

At one point, Moss ranked as a better prospect than Dustin Pedroia and Jon Lester. He’s had some good years, most notably with the Athletics, but is a .783 career OPS good for a one-dimensional, hit-first first basemen? Not really. Hansen was a complete bust– a young reliever with a high-90’s fastball and wipeout slider, but couldn’t throw a strike. He was out of the game at age 25. Meanwhile, Bay had a .921 OPS as an All-Star in 2009 with Boston.

  • December 2010: Sent Casey Kelly (1) and Anthony Rizzo (3) to San Diego for Adrian Gonzalez

The last big deal during Theo’s time in Boston. People forget that Kelly was actually the main piece of the trade for the Padres. Ranked the #1 prospect in the Red Sox system following the 2009 and 2010 seasons, Kelly has probably been the biggest bust amongst Theo’s traded-away bunch. He struggled to stick in the Padres(!) rotation before being traded to Atlanta prior to 2016– where he’s been up and down between the majors and AAA. He has a career 6.39 ERA. Rizzo has transformed from a young star into one of the game’s best players. Since 2013, he ranks 15th in the league with 16.5 WAR. Gonzalez had an .895 OPS during his 1+ seasons in Boston, but was also part of the 11′ collapse which marked the end for Theo.

  • January 2012: Sent Andrew Cashner (3**) to San Diego for Anthony Rizzo

Theo’s biggest mistake during his time in Boston was trading away Anthony Rizzo. So what did he do as one of his first trades with the Cubs? He got Rizzo back. Talk about a steal. Cashner hasn’t been bad– he has a 3.66 ERA and 3.64 FIP in five seasons with the Padres– but he’s not a top-15 pitcher. Rizzo is a top-15 hitter.

I think if you asked Theo how many of these trades he’d do again, he would say all but two (Sanchez and Rizzo #1). You can even argue that, without the Sanchez trade, there’s no Schilling. And the other mistake Theo made was remedied by getting the guy back he lost in the first place. Not bad.


*according to

**according to


Posted by Jeb

From the great "vacationland" state of Maine. Former D3 baseball player on an underachieving team. Prior: TrackMan with A's. Current: Check Down Sports. Soon: Video with Reds. All-time facial hair lover.

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