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Red Sox first round picks in the Theo Epstein era

MLB: General Managers Meetings Joe Camporeale-USA TODAY Sports

The head of the Red Sox front office, whether it was General Manager or Director of Baseball Operations or now Chief Baseball Officer, has had a lot of turnover over the last decade. There was a long stretch when Theo Epstein was in town, but the team has had three more since he left at the end of the 2011 season. With this in mind, I thought it would be a good exercise to compare the first round selections for each and how those selections have (or have not) led to four championships since 2004. First, I asked the Twitter-sphere which GM they preferred and Theo got the overwhelming majority of support.

Keep in mind, the pre-2013 draft was a very different beast. During that time, free agents were put into one of three buckets: Type A (player ranked in the top 20% of players at his position, Type B (player ranked between 20% and 40% at his position), and then everyone else. I will begin with Epstein this week and then follow up with Ben Cherington and Dave Dombrowski.


When Larry Lucchino left San Diego to take the CEO position, he brought along Theo Epstein, who was the Director of Baseball Operations with the Padres at the time, to work with him. He became the interim General Manager, replacing Mike Port at the conclusion of the 2002 season. During those first couple of seasons, he was credited with making trades and signings that led the team to its first World Series championship in 86 years. During his tenure, he made some great first round picks in the draft but also used those players to trade for the likes of Adrián González and Víctor Martinez.

2003

David Murphy (17th Overall)

Matt Murton (32nd)

Murphy played one year with the Red Sox before being traded in 2007 for Eric Gagne. Murton, meanwhile, was a compensation pick for Cliff Floyd, who the Red Sox had traded for in the previous July. Murton, along with Nomar Garciaparra, was quickly traded to the Cubs in 2004 for Orlando Cabrera as Epstein wanted to shore up the infield defense. I’d say both of those decisions worked out pretty well as the Red Sox went on to win the World Series in both years.

2004

N/A

After signing Keith Foulke, the Red Sox lost their first round pick to the Athletics, who used the pick to draft Landon Powell. Boston’s first pick that year ended up being in the second round, and they used that selection to take Dustin Pedroia. I’d say that was a win.

World Series - St Louis Cardinals v Boston Red Sox - Game Six

2005

Jacoby Ellsbury (23rd)

Craig Hansen (26th)

Clay Buchholz (42nd)

Jed Lowrie (45th)

Michael Bowden (47th)

After winning their first World Series in 86 years, the Sox lost a bunch of key players to free agency in the winter before the 2005 season. Pedro Martínez signed with Mets and the Red Sox received the 42nd overall pick, which they used to draft Buchholz. After losing Orlando Cabrera, they received two picks from theAngels, which they used on Ellsbury and Jed Lowrie. After Derek Lowe signed with the Dodgers, the Red Sox picked up two more picks, which they used on Hansen and Bowden. Hansen played in five seasons in the majors. three year with the Red Sox and two with the Pirates, but struggled in the bullpen with a 6.37 ERA. Interesting to note that Hansen was included in a three-team trade that sent him and Brandon Moss to the Pirates, Jason Bay to the Red Sox and Manny Ramirez to the Dodgers. Bowden, who ranked as highly as the number two prospect in the system by Baseball America in 2008, made his debut with the Red Sox the same year but struggled with walks and a lack of strikeouts.

2006

Jason Place (27th)

Daniel Bard (28th)

Kris Johnson (40th)

Caleb Clay (44th)

The Red Sox saw another big free agent leave following the 2005 season as Johnny Damon signed with the Yankees. In return, they received the 28th and 40th overall picks and used those to select Bard and Johnson. Bard was, of course, an absolute beast setting up Jonathan Papelbon from 2009-2011. His best season was in 2010 when he appeared in 73 games with a 1.93 ERA and 1.00 WHIP. The Red Sox made him a starting pitcher in 2012 and unfortunately his career went down hill from there. He lost all his command and in the 10 games he started he posted a 6.22 ERA with a 1.74 WHIP. Johnson made it up to Triple-A and fourth ranked pitching prospect in the system by Baseball America but never made it to Fenway. He was released in May 2011 but did see some major league time with the Pirates and Twins. His contract was sold to the Hiroshima Toyo Carp in the Nippon Professional League in Japan and performed very well. He started 28 games in 2018 and finished the season with a 1.85 ERA and 1.09 WHIP.

The Red Sox also lost Bill Mueller to free agency and was awarded the 44th overall pick, which was used to draft Caleb Clay, a prep right-handed pitcher from Alabama. Unfortunately, he never made it to the big leagues and topped out at Double-A in the Red Sox organization. The most disappointing pick from this first round was Jason Place, a prep outfielder known for his speed and power. However, as he moved up the ranks, his strikeout rate also moved up. He never made it past Double-A and retired from baseball in 2011.

2007

Nick Hagadone (55th)

Ryan Dent (62nd)

After losing Alex Gonzalez and Keith Fouke, the Red Sox were able to draft Hagadone and Dent during the compensation phase of the first round. Hagadone only made it to Salem before being traded along with Justin Masterson and Bryan Price for Víctor Martínez in 2009. He made it to the majors with the Indians was in their bullpen from 2011-2015. Ryan Dent, a prep middle infielder, never really hit in the minors and topped out at Triple-A.

2008

Casey Kelly (30th)

Bryan Price (45th)

After losing Eric Gagne, the Sox used their compensation pick on Price, a right-handed pitcher from Rice University. As mentioned previously, he went along with Masterson and Hagadone in the trade with the Indians for Martínez. The Indians put him in the bullpen after the trade and he had a couple of great seasons in the minors but after a poor outing in the majors he decided to retire rather than accept a demotion back to Triple-A in 2014. The better prospect at the time was the 30th overall pick, Kelly. He was drafted as a pitcher but the right-hander wanted to play shortstop. In his first professional season in Greenville and Salem in 2009, Kelly moved from the mound to shortstop but after hitting .224 and striking out 25.8 percent of the time, he decided pitching was a better avenue for him. He, along with Anthony Rizzo, Reymond Fuentes, and Eric Patterson were traded in the winter of 2010 for then All-Star first baseman Adrián González of the San Diego Padres. Kelly was the Padres top prospect but after after straining his elbow in 2012 and then having TJS in 2013, he went to the bullpen and unfortunately never found his stride again.

Boston Red Sox v Baltimore Orioles Photo by J. Meric/Getty Images

2009

Reymond Fuentes (28th)

Fuentes was not with the Red Sox long after being drafted in 2009. After hitting .270/.328/.377 with Greenville in 2010, he was part of the aforementioned deal with San Diego for González.

2010

Kolbrin Vitek (20th)

Bryce Brentz (36th)

Anthony Ranaudo (39th)

After losing Type A free agent Billy Wagner to the Braves, the Red Sox picked Kolbrin Vitek and Anthony Ranaudo. Vitek transitioned from the outfield to third base after being drafted but never made it past Double-A. Ranaudo was the better prospect of the two and made it to Fenway for a couple of starts in 2014. In the offseason prior to the 2015 season, he was traded to the Rangers for Robbie Ross. He bounced around the minors with the Rangers and White Sox before playing in Korea in 2017.

Bryce Brentz was selected with the 36th overall pick and is still in the Red Sox system, after a gap year with the Mets in 2018. The outfielder has played a few games in the majors but struggled to make contact throughout his career.

2011

Matt Barnes (19th)

Blake Swihart (26th)

Henry Owens (36th)

Jackie Bradley Jr. (40th)

The 2011 draft was the last draft Epstein would participate in before moving on to the Cubs, and overall it was one of the best drafts of all time. After losing Adrian Beltre to the Rangers in the winter, the Red Sox received two draft picks and selected Swihart and Bradley Jr. It would have been nice to have Beltre on the team for sure, but Bradley and, to some extent, Swihart, were part of the 2018 World Series run. After the Tigers signed Víctor Martínez, the Red Sox used their two compensation picks there on Matt Barnes and Henry Owens, the former also being a contributor to that 2018 run.

Looking back on the Theo era, I’d say he and his front office did a great job in recognizing talent in the draft. Espstien was also great a trading prospects at the right to get major-league talent in order to compete. In doing this exercise and then looking at the Cubs farm system, I wonder if the change in draft rules hurt his ability to load up on first year talent which he could use as trade chips in the future. Next week, we will look at Ben Cherington and Dave Dombrowski’s time in Boston.