Theo Epstein has now led the Red Sox and Cubs to World Series titles and is a shoe-in Hall-of-Famer as an executive. A huge part of his success is due to an extremely good track record in the MLB draft, a notorious crapshoot that is hard to get right no matter where you are picking. Here are his best 8 picks, taking both talent and value into consideration. (Note: he joined the Cubs in October 2011, the draft is in June)
8. Kris Bryant 2nd overall in 2013
He may well be the best player on this list, but he was also the most obvious pick. Everyone knew he was going #1 or #2 that year; it was just a matter of who ended up selecting there. Still, that being said, the MLB draft is a completely unpredictable shit show and teams have screwed up more obvious picks than Bryant.
7. Jacoby Ellsbury 23rd overall in 2005
At the time Ellsbury was coming off of a spectacular College World Series run where he basically was turning walks into runs by stealing 2nd, 3rd, and home plate. He was a complete dynamo. But that didn’t mean he was the obvious selection at #23. Theo could have easily taken Craig Hansen in the 23rd spot, hoping that Ellsbury would fall to him at 26 (which is where he ended up taking Hansen). If that happened, chances are Ellsbury gets snagged at #24 or #25 and the Sox only end up with Hansen, who turned out to be a major bust despite a storied amateur and minor league career. Ellsbury has been a disappointment with the Yankees, but his Red Sox career alone (2nd in the MVP race in 2007) makes this pick an unqualified success.
6. Jackie Bradley Jr. 40th overall (1st round) in 2011
Bradley was a college star and made sense at the time, but even Theo himself passed on him three times to take Matt Barnes, Blake Swihart, and Henry Owens ahead of him in the 2011 draft. Bradley took a couple years to get going, but has become a Red Sox starter over the past year and a half. His defense in center field is Gold Glove-worthy and his offense has been better than expected.
5. Kyle Schwarber 4th overall in 2014
Schwarber was highly touted, but far from a consensus pick because of his perceived defensive liabilities. Most National League teams probably would have passed on him in the #4 slot because they couldn’t imagine a place for him in the field. Theo Epstein took the opposite view, deciding that the pudgy (then) catcher possessed rare offensive abilities that would help the Cubs no matter where he played in the field. While Schwarber is still only 23 and has been injured for more than half of his time in the big leagues, he put up an .842 OPS in 232 at-bats in 2015 and was an impact player (and possibly the difference maker) in the 2016 World Series. Kid has the potential to be a left-handed Miguel Cabrera.
4. Dustin Pedroia 65th overall (2nd round) in 2004
There was never a question about the talent with Dustin Pedroia. He was a star for a loaded Arizona State team and even pushed Ian Kinsler out of the starting shortstop role, forcing him to transfer to Missouri. The issue was his size and whether he would excel at 2nd base in the big leagues. Theo decided to focus on Pedroia’s production and reputation as a gamer, not his 5’8 frame, and his bet paid off spectacularly. Petey was rookie of the year in 2007 and won the MVP in 2008. Since then he has finished in the top-10 in MVP voting twice and won multiple Gold Gloves on the way to being recognized as the best defensive second baseman in the majors.
3. Jonathan Papelbon 114th overall (4th round) 2003
This was some true masterpiece-type shit right here. Papelbon was pretty much off the radar as a closer at Mississippi State, going 9-6 with a 2.90 ERA over three seasons with the team. He was originally drafted by Billy Beane and the A’s in the 40th round in 2002, but decided to go back to school and “get his degree,” aka improve his draft stock. Honestly, the fact that Papelbon has a diploma makes us question Mississippi State as an academic institution, but we digress. After originally trying Papelbon as a starter with mixed results (he only had two pitches), the Red Sox finally decided to move him to closer in 2006 when Keith Foulke faltered, and the rest is history. He is now 9th ALL TIME in saves in MLB history.
2. Anthony Rizzo 204th overall (6th round) in 2007
The value here is insane. Although Theo drafted Rizzo with the Red Sox, he now stars for the Cubs after Theo originally dealt him to San Diego as part of the Adrian Gonzalez trade in 2010 and then acquired him for the Cubs in January 2012 as part of the Andrew Cashner trade. He obviously took a while to get going – hence all the trades – but Theo never gave up on him and now at the age of 27 he is coming off three straight All-Star appearances and looks like a lock for a second straight top-5 MVP finish. Pretty good value with the 204th overall pick.
1. Mookie Betts 172nd overall (5th round) in 2011
Betts has assumed the role of Red Sox cornerstone piece of the future. A tremendous outfielder and power hitter, Betts’ plate discipline and approach are improving by the day. Despite his MVP caliber season in 2016, he still has the potential to be even better, a scary proposition for the rest of the American League. In addition to his insane talent, what makes this draft pick #1 on our list is the fact that Betts wasn’t very highly rated coming out of school and Theo plucked him out of the 5th round in one of his last selections for Red Sox.