Given that fact, I thought it would be a good time to take a look at Theo's draft record in his first five seasons. Anything past 2007 is hard to judge, especially with so many high school picks there, but the players drafted in 2003-2007 are pretty much established by now.
The top of the 2003 draft was headlined by guys who never really lived up to their potential. With their first rounder, sandwich pick, and two second rounders the Red Sox picked three college players - David Murphy, Matt Murton, and Abe Alvarez, along with high school outfielder Mickey Hall. All four are no longer with the Red Sox, in fact, none lasted past 2009. Matt Murton was a throw in to the 2004 Nomar Garciaparra/Orlando Cabrera trade, which of course helped the Red Sox win a title. David Murphy returned a lot less in terms of value, fetching the ironically named (at least in his stint with the Red Sox) Eric Gagne at the 2007 trade deadline. Abe Alvarez was released in May of 2008. Always a better story than a pitcher, as he was legally blind in his left eye, Alvarez never was able to get by with his mediocre stuff. The last man standing from the group, Mickey Hall, was traded for the immortal Paul Byrd in August of 2008. Much like the following draft, there is one player who saved this entire draft class, the 5th round pick of Jonathon Papelbon. Although he was drafted as a starter and the organization waffled back and forth about whether or not to shift him to the rotation, Papelbon is clearly one of the elite bullpen arms in the game right now. With free agency looming and Papelbon putting up one of the best seasons of his career, it will be an interesting off season for the Red Sox. With money tight for most teams, and the market flooded with relievers, I think the Red Sox will find a way to resign Papelbon to a fairly reasonable contract. If Papelbon does leave, it would mean that no players from the 2003 draft class are still in the Red Sox organization.
Total WAR: 25.4
Top player: Papelbon (16.7)
The 2004 draft was a bit thinner, in part due to having no first round or sandwich round pick, thanks to signing free agent reliever Keith Foulke. But they sure made their one early pick count, selecting Dustin Pedroia. The Pedroia story is probably familiar to most of you - he has no "tools" that scouts love - he's extremely small, he isn't that fast, and his swing looks pretty damn ugly; but all he does is hit. Originally a shortstop, the Red Sox made him their starting 2B coming in to the 2007 season. After struggling in a cup of coffee in 2007 (.191/.258/.303 in 89 at bats), Pedroia struggled mightily in April (.182/.308/.236), leading to many to wonder if he could hit major league pitching. Pedroia erased those concerns with a spectacular May and June, and has been a Red Sox lineup staple ever since. Cla Meredith was the only other player from the 2004 draft with significant time in the majors. After panicking over Josh Bard's inability to catch Wakefield's knuckle ball, Bard and Meredith were shipped out to San Diego in exchange for former Red Sox Doug Mirabelli in 2006. Meredith had an excellent 2006 for the Padres (1.07 ERA, 0.71 WHIP), but slowly slid toward mediocrity. He was later traded to the Orioles, who eventually released him. After undergoing Tommy John surgery in 2011, Meredith's time in the majors may very well be over.
Total WAR: 26.4
Top player: Pedroia (24.1)
The 2005 draft has received lots of publicity lately as one of the most successful in recent memory. In it, the Red Sox added three major pieces to their current roster (Jacoby Ellsbury, Clay Buchholz, and Jed Lowrie), along with relief prospect Michael Bowden. This class has also been extremely injury prone - Buchholz has alternated being hurt and ineffective all season, Ellsbury had a lost 2010 sandwiched between elite seasons in 2009 and 2011, and Jed Lowrie has had too many injuries to list. The 2005 draft also includes one of the biggest misses in the Epstein era, St. John's relief pitcher Craig Hansen. Hansen was supposed to be the most polished arm in the draft, and was expected to help the mediocre Red Sox bullpen as soon as that season. Hansen struggled in his major league debut in 2005, had his mechanics repeatedly tinkered with, and never amounted to much of anything. Hansen was supposed to be the new closer, allowing Papelbon to slide to the rotation. Instead, he was worse than replacement level (-2.2 WAR). I'm not sure if it was the pick or the handling of Hansen, but either way it just didn't work out. There were not many major league contributors picked after Hansen, Colby Rasmus two picks later does stand out, though. Interestingly, most of the major leaguers after Hansen were actually picked by the Red Sox (Buchholz, Lowrie, and Bowden all went in the supplemental round).
Total WAR: 23.3
Top player: Jacoby Ellsbury (12.9)
The 2006 draft includes players who are either still establishing themselves or have moved on from the organization. With their first round pick, the Red Sox went with pure stuff, picking Daniel Bard. Despite serious control problems in college, which cropped up again in the minors (in A ball in his first season he walked an incredible 8 /9 IP in over 60 innings), the Red Sox succeeded in transforming Bard into an elite reliever, and a potential replacement for Papelbon. Bard has established himself as an old school fireman, throwing 75 innings last year and is on pace for the same total this year. The two supplemental round picks, Caleb Clay and Kris Johnson, both appear to be misses. Johnson was released in May, while Caleb Clay is struggling in AAA and may be released in the next year. Outside of the first round, the Red Sox did very well, though. In the second round, the Sox picked Justin Masterson, who was eventually a key piece in their trade with the Indians for Victor Martinez. Initially a starter, Masterson was transitioned to a relief role due to his struggles with left handed hitters. The Indians converted him back to a starter, where he put up mediocre numbers in 2009 and 2010, despite extremely good strikeout, walk, and ground ball rates. Something has clicked in 2011, as he has emerged as Cleveland's clear #1 pitcher, posting 3.01 ERA and 1.23 WHIP. The peripherals are fairly similar, with a better walk rate in 2011. Interestingly, although he's improved against lefties (.784 OPS in 2010, .700 in 2011), his absolute dominance of right handed hitters this season may be a bigger key to his success (.681 in 2010, .584 in 2011). The Red Sox have been high on Masterson even after the trade, supposedly trying to reacquire him at the 2010 trade deadline, so I think it is fair to count him as a feather in Theo's cap. Also included in this draft are current Red Sox outfielder Josh Reddick (17th round) and solid performer from 2010 Ryan Kalish (9th round), who unfortunately has had a bit of a lost season due to several injuries, the most recent being a neck injury requiring surgery.
Total WAR: 15.1
Top player: Justin Masterson (6.4)
So which draft class wins? Despite the lower total WAR, even if you exclude Hansen's -2.2, I think the 2005 class will ultimately contribute more wins to the Red Sox. But, they also had a hell of a lot more picks that draft. If you're going for quality, it is hard to go wrong with hitting on Dustin Pedroia with your single early draft pick. Don't forget that the last two drafts pre-Theo added some key contributors too. Mike Port picked Jon Lester (23.1 WAR), who would still be under his original contract had he not signed an extension, in the second round of the 2002 draft and Dan Duquette drafted Kevin Youkilis in the 8th round of the 2001 draft. Interestingly, the Red Sox also drafted catcher Jeremy Brown in the 19th round, although he did not sign. Brown was later drafted and signed by the Athletics, and both Youkilis and Brown went on to play prominent roles in Michael Lewis' book "Moneyball".
Feel free to weigh in about which draft class you think is most impressive in the comments.