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July 22, 2020 at 12:30 PM

Revisiting the 2008 draft: A small step back

Thank you for checking in on the newest entry in our draft retrospective series. Yesterday was a pick-by-pick rundown of 2008, while today we will dig a little deeper into a few of the more interesting and prominent draftees. For a quick list and links to player pages, check out our Draft History page.

2008 MLB Draft

The Red Sox won their first World Series in a long three years in 2007, leading the team to pick at the back end of the draft. While Boston is typically active in the free agent market, Theo Epstein took a different approach and focused on bringing the band back together for 2008, re-signing Curt Schilling, Mike Lowell and Doug Mirabelli, in addition to picking up the options for Tim Wakefield and Julian Tavarez. Matt Clement and Eric Gagne were the only major league free agents to depart the squad and only Gagne was a Type A or B free agent, netting the Red Sox the No. 45 overall pick in the first supplemental round. Boston also did not sign Hunter Morris, its third-round pick in 2007, which gave the organization the No. 85 overall pick.

While the draft did not net the kind of high-end talent we have seen in the previous editions of this series dating back to 2003—only two of the 29 players signed by the Red Sox were featured on a Baseball America Top 100 list and the players signed have combined for -1.2 bWAR—nine spent time in the major leagues (with an additional four that the team failed to sign reaching the show). Interestingly, six of those nine players played out their major league careers in other organizations, as Epstein made use of many of these players in trades. The club made five selections in the first three rounds, and three of those players were packaged in trades for major league talent before making the big leagues themselves, and another was traded after fewer than 25 innings in Boston.

The Vitals
General Manager: Theo Epstein
Scouting Director: Jason McLeod

Major Leaguers drafted and signed
Christian Vazquez (9th round, 2.9 bWAR)
Stephen Fife (3rd round, 0.8 bWAR)
Hunter Cervenka (27th round, 0.2 bWAR)
Bryan Price (1st supplemental round, -0.2 bWAR)
Carson Blair (35th round, -0.4 bWAR)
Kyle Weiland (3rd round, -0.9 bWAR)
Ryan Lavarnway (6th round, -1.1 bWAR)
Tim Federowicz (7th round, -1.1 bWAR)
Casey Kelly (1st round, -1.4 bWAR)

Unsigned players who reached the major leagues
Yan Gomes (39th round, 13.4 bWAR)
Travis Shaw (32nd round, 9.4 bWAR)
Anthony DeSclafini (22nd round, 6.6 bWAR)
Brian Flynn (18th round, 0.9 bWAR)
Alex Meyer (20th round, 0.8 bWAR)

Compensation consideration
Received supplemental first-round pick for loss of free agent Eric Gagne
Received supplemental third-round pick for failure to sign Hunter Morris 

Stocking up on backstops
The Red Sox selected and signed three catchers in the first nine rounds of this draft, also turning a later-round shortstop into a fourth catcher. They also drafted and failed to sign two catchers. Of those six backstops, five of them went on to play in the major leagues. Two of those backstops, Christian Vazquez and Yan Gomes, are among the three most valuable players from the Red Sox' 2008 draft class. While the number of catchers taken was not abnormal, the draft capital invested in the position was unique. Epstein and McLeod dipped into the catcher well with Ryan Lavarnway in the sixth round, Tim Federowicz in the seventh round and Christian Vazquez in the ninth round.

The Red Sox would not select a catcher that high in the draft again until 2011, when Blake Swihart was a first-round selection, with Lavarnway was the highest catcher the organization had picked since Jon Still in the fourth round in 2006. Taking Vazquez in the ninth was the earliest that the Red Sox have selected their third catcher in a draft during the SoxProspects era by a significant margin—the next-earliest that the third catcher was picked was when the Red Sox selected their third catcher in the 17th round in both the 2016 and 2018 drafts. That use of resources paid off, as this draft accounts for four of the six catchers drafted and signed by the club to make the major leagues since the 2003 draft.

The resources spent on Federowicz, Lavarnway, Vazquez, and Blair included $755,000 in bonus money, as well as three top-ten picks, and each of the three resulted in varying degrees of success. Vazquez has been a mainstay behind the plate for Boston over the past few years, while Federowicz was used in a trade and Lavarnway played 97 games for the Red Sox over four seasons. Blair was the exception in that the MLB club didn't get value from his development, but success drafting and developing another MLB catcher, especially one who'd been an infielder previously, must be seen as a development win.

Vazquez is the most valuable player that the Red Sox were able to sign in the draft, contributing 2.9 bWAR over his time in the majors so far, of which 2.3 came in 2019, when he really hit his stride in the batter's box. The Puerto Rico product signed for just $80,000, but eventually developed a sterling defensive reputation highlighted by a weapon of an arm—one he at times fell a bit too in love with. He was able to do all of this even after repeating the Gulf Coast League to start his first full season, which is typically an extremely poor harbinger of a player's future prospects with the team. However, Vazquez may have been the ideal candidate to do so, having been only 17 years old when drafted and playing the most demanding defensive position to develop in the game. 

Vazquez was not poor with the bat in his first two major league seasons in a three-way split for reps at the catcher position, with a missed season in 2015 after Tommy John surgery. He hit for average in 2017, but after a down 2018, had a breakout year last season. Vazquez slashed .276/.320/.477 with a career-high 23 home runs, more than doubling his career total of 10 heading into the year. He is under team control through 2022 at a reasonable price and will likely be part of the Red Sox for the foreseeable future.

While Federowicz has become a quintessential "AAAA" player, he can still be considered a development success because of the return in his eventual trade. The North Carolina draftee had varying degrees of prowess with the bat through his first three professional seasons, but was in no way a liability in the batter's box, especially considering his position. Having earned a stellar reputation for his work on the defensive side of the game that is likely responsible for his continued chances, he was likely at the peak of his value in the summer of 2011, slashing .277/.338/.407 for Double-A Portland. The Red Sox traded for Erik Bedard in a three-way deal with the Dodgers and Mariners on July 31, 2011 for the stretch run, with Federowicz joining Stephen Fife and Juan Rodriguez in Los Angeles, while Josh Fields came from Seattle with Bedard. Federowicz played more than 25 games in a season just once, while Bedard was acquired to aid in a playoff run.

Lavarnway has similarly managed only to bounce between Triple-A and cups of coffee in the majors, but was able to climb to the top and play at Fenway. A bat-first catcher, he faced constant questions during his development of whether he would be able to stick at the position despite his below-average defensive skills, although some thought he might hit enough to make an impact anyway. The Yale product destroyed Ivy League pitching and had a similar experience with minor league arms, winning two Offensive Player of the Year awards both from the organization and from this site. There was little doubt he would hit as he came up, as the questions were rather about his defense. However, he has posted just a .211/.270/.343 line in just over 400 MLB at-bats since 2011, leading to his joining Federowicz as an up-and-down catcher.

Casey Kelly: A Two-Way Player Before It Was Cool
Casey Kelly was Boston's first-round selection in 2008. Drafted as both a right-handed pitcher and a shortstop, Kelly wanted to continue to hit and the team allowed him to do so with a unique development plan for him for the 2009 season. Kelly played shortstop-only the year he was drafted in the Gulf Coast League and Lowell, as it was not atypical for the Red Sox to ease high school pitchers into the pros with a very limited workload after signing. For his first full season, Kelly began the year on the mound making nine starts in Greenville before moving up to Salem for eight more before being shut down after July 7. His strikeout numbers didn't jump off the page, but Kelly, the son of a minor league manager, showed an advanced feel for pitching, making easy work of the South Atlantic League at age 19 with a 1.12 ERA. While that figure did jump nearly two runs against High A hitters, Kelly kept his WHIP to 0.86, showing the potential to move quickly on the mound. He then switched gears and returned to Fort Myers, having essentially a second Spring Training (which we apparently now call Summer Camp) and playing 8 GCL games before returning to Greenville as a shortstop. Perhaps he wasn't quite put in a position to succeed, having not seen pitching for months, but he hit just .224/.305/.313 over 32 games, followed by a .171/.261/.244 line during an incredibly aggressive assignment to the Arizona Fall League to get him some more at-bats.

Perhaps it was the organization's plan all along, or perhaps not, but the writing was on the wall at this point—Kelly stood a chance to move MUCH faster as a pitcher than a hitter, and it was his promise on the mound that made him a top-30 prospect in the game following his unique first full season. While he could have hoped, at best, to head to Salem again as a shortstop in 2010, and would have to show he didn't need more seasoning in Greenville, he had a chance to jump right to Portland as a pitcher. After making the obvious choice to focus on pitching, that's just what Kelly did. Had Kelly come along in the present day, when the success of Shohei Ohtani has apparently made teams so much more willing to use two-way players in the Majors that MLB instituted a new rule for such usage, it is unclear if his development would have been handled differently, but it is fun to think about.

Kelly's line with the Sea Dogs in 2010 wasn't pretty, as he sported a 5.31 ERA and 1.61 WHIP, but he was still more than four years younger than the weighted average of all players in the Eastern League that season as a 20-year-old, and he remained a consensus top-50 prospect in baseball headed into the 2011 season. Before getting a second shot at Portland, he was sent to San Diego with Anthony RizzoReymond Fuentes and Eric Patterson for Adrian Gonzalez. The Red Sox' corner infield situation was drastically changing heading into the 2011 season, with Mike Lowell retiring and Adrian Beltre departing in free agency. Gonzalez was one of the best hitters in the majors at the time and it would take two first-round picks in Kelly and Fuentes, along with the reigning Red Sox minor league hitter of the year in Rizzo, to pry the first baseman away from San Diego.

Kelly was traded at the peak of his value, making his MLB debut for San Diego in 2012 and pitching 29 innings before tearing his UCL and undergoing Tommy John surgery in March 2013. He returned and pitched 54 more MLB innings between 2014 and 2018, mostly serving as Triple-A depth, before going abroad to play in Korea in 2019, where he has carved out a role in the LG Twins' rotation.

Trading for major leaguers
The Red Sox were in the middle of a long competitive window in 2008, entering the year as the reigning World Series champions and having won another title, famously, in 2004. The team had also made the playoffs in four of the last five years, combined with another postseason appearance in 2009. Boston also won at least 85 games every year from 2002-2011, the first decade with the new ownership group.

One necessity of fielding a competitive team every year is a willingness to use prospects as trade chips to bring immediate help to the major league roster. Three of the first four players selected in this draft were traded away as minor leaguers, while Kyle Weiland, the team's fifth selection, was dealt after fewer than 25 major league innings pitched. Two additional players signed by the team during this draft were be packaged for more established players and in most cases, the prospect was traded near the peak of his value.

This strategy was helped by the strong drafts of the years prior, giving the team players like Dustin Pedroia, Jacoby Ellsbury and Clay Buchholz to form a young core and create depth in the minor leagues to trade for what Epstein and the baseball operations teams perceived as team weaknesses. Additionally, a 40-man roster crunch headed into the 2011 offseason would have required the addition of several players the roster to be protected from the Rule 5 Draft. With this situation coinciding with an attempt at a playoff run, the time was high for trades involving 2008 draftees.

Chronologically, Bryan Price, a selection in the first supplemental round, was traded first. On July 31, 2009, Price was sent to Cleveland, along with Justin Masterson and Nick Hagadone, in exchange for Victor Martinez. Hagadone was the team's first-round selection in 2007, while Masterson was the headliner and was in his second full season in Boston as a swingman. At the close of play on July 30, Boston was two-and-a-half games behind the Yankees for first place in the American League East and led the wild card race by one-and-a-half games over Texas. Jason Varitek was 37 years old and struggled behind the plate, slashing just .209/.313/.390. On the other side, Masterson was an expendable piece in a bullpen that included Jonathan Papelbon, Takashi Saito, Ramon Ramirez and Hideki Okajima, all of whom touted an ERA+ of more than 125 on the season.

Martinez hit .336/.405/.507 in 56 games after the trade and provided a shock of offense. While New York played nearly .700 ball down the stretch, won the World Series and would not be caught in the AL East, the Red Sox continued on their strong pace, winning 95 games and taking the American League Wild Card berth by eight games over the Rangers, tying for the third-best record in baseball. Price would pitch only 2 2/3 innings for the Indians before being released, while Martinez would reprise his strong second half with an All-Star Game appearance in 2010.

Kelly was moved during the 2010-11 offseason, as described above.

Stephen Fife and Tim Federowicz were dealt to the Los Angeles Dodgers in a three-way deal with Seattle at the 2011 trade deadline in an attempt to bring pitching help to Boston for the stretch run, as Erik Bedard came from the Mariners. Boston was two-and-a-half games up on the Yankees in the division on the day of the trade. Fife and Federowicz were both in Portland at the time. Fife was pitching much better than he had in his first try with the Sea Dogs in 2010, while Federowicz was having something of a breakout year, slashing .277/.338/.407.

Through August, the Red Sox held serve with the team from the Bronx, with a one-and-a-half game lead on August 31 and a nine-game cushion on the Rays, who held the wild card spot. However, Boston's 7-19 September caused the team to miss the playoffs completely. This was through no fault of Bedard, who pitched to a 107 ERA+ after the trade and would leave as a free agent amid the overhaul that followed. Both Fife and Federowicz would make the major leagues, but were near replacement-level players and once their three options were used, departed the Dodgers' organization.

Weiland, who had just made his major league debut, was traded in December 2011 along with Jed Lowrie to Houston for Mark Melancon. The injury bug came soon after for the Notre Dame product, as he threw just 34 2/3 innings in affiliated baseball after the trade. 

Hunter Cervenka was the player to be named later in an agreement with the Cubs to bring Marlon Byrd to Boston and while he eventually did make it to the big leagues, it was in 2016 with Atlanta. He also would play for the Marlins.

While the relative lack of MLB success of the players drafted makes this a less attractive list of draftees than the five drafts we've already covered in this series, the fact that the Red Sox were able to turn some of those prospects into useful major leaguers like Martinez and Gonzalez, and to a lesser extent, Bedard, can be seen as a development win. Success doesn't always come from developing the next Dustin Pedroia or Anthony Rizzo, which is something we came to learn—to a much more extreme degree—a little under a decade later.

A continuing focus on tall pitchers
The 2008 draft established a several-year trend of targeting pitchers of significant height. Tall pitchers were not new to the organization, as the team had taken Justin Masterson and Nick Hagadone in 2006 and 2007 respectively, but it was beginning in 2008 that a significant number of the high-profile arms the club drafted seemed to be six-f oot-three at a minimum. Part of the strategy was that the additional extension from tall pitchers created greater effective velocity, as the release point was closer to home plate. This would be met with mixed results over the next several years with arms such as Alex Wilson, Anthony Ranaudo, Brandon Workman, Matt Barnes, Henry Owens, Pat Light, Ty Buttrey, and Trey Ball.

After selecting high-schooler Casey Kelly in the first round, Theo Epstein and Jason McLeod dipped hard into the college pitching well, specifically tall right-handers, and this proved to result in major league talent. Three of the next four picks were college right-handed pitchers, the shortest of whom was 6-foot-3. Two other later-round picks also fell into the demographic and both had size as well.

Bryan Price, who was traded just over a year after he signed, was the team's supplemental first-round pick and stood at 6-foot-4, 200 pounds. The Texan threw in the mid-90s and had pedigree. He pitched for Rice, which made the College World Series all three years he was a member of the team and also earned a national seed in the NCAA Tournament each season. Part of Price's intrigue was that he was used almost exclusively as a reliever for the Owls, having thrown only 65 2/3 collegiate innings across 46 appearances. The Red Sox were going to try him as a starter and he had already made eight starts for Salem when he was sent to Cleveland as part of the aforementioned trade that brought Victor Martinez to Boston. 

After selecting infielder Derrik Gibson in the second round, a pitcher was next on the Red Sox' draft card in Stephen Fife. Fife was listed at 6-foot-3, 215 pounds and played college ball at Utah, when the Utes were a member of the Mountain West Conference. Fife was a member of the starting rotation in 2008 and threw softer than Price, but had a delivery with deception and threw lots of strikes, resulting in weak contact. The native Idahoan was likely too advanced for Lowell and Greenville, featuring a WHIP of below 1.00 as a starter. He settled into more average numbers in Salem and Portland and was in his second year with the Sea Dogs, improving his K/BB and K/9 ratios in his second go-around when he was dealt.

Injuries derailed his major league career before it really got going, but 6-foot-4, 195-pound Weiland was the team's third-round selection out of Notre Dame. Like Price, Weiland was mostly a bullpen arm for the Fighting Irish and was stretched out as a starter after he was drafted. Weiland advanced quickly through the system, earning an aggressive Salem assignment in 2009, followed by Portland in 2010, Pawtucket in 2011 and Boston that July. In seven appearances, five of which were starts, Weiland contributed 24 2/3 innings to the ill-fated 2011 team, pitching to a 7.66 ERA.

In later rounds, the team would turn its attention to some larger-bonus high school arms with a continued focus on height. Though the team fell short in its pursuit of six-foot-nine Alex Meyer despite an offer north of $2 million, they did hand out six-figure bonuses to Tyler Wilson (six-foot-six), Richie Wasielewski (six-foot-four), and Kyle Stroup (six-foot-five). Perhaps as an early warning, it was Hunter Cervenka, who stood, a runt-like six-foot-one, who established himself among the bonus babies. 

Tragedy strikes a rising star
Ryan Westmoreland had all the makings of a star. He was a local product, from Portsmouth, Rhode Island, and had an incredible debut for Lowell in 2009. He slashed .296/.401/.484 in 223 at-bats across 60 games, adding 19 steals. He rose up prospect lists and was ranked in the top 25 by Baseball America. It seemed he was on the fast track to roam the field at which he had grown up attending games.

He started to feel numbness in his right side during Spring Training in 2010 and an MRI revealed a cavernous malformation on his brain stem. The condition made him susceptible to brain bleeds, which can result in death. He had surgery to repair the issue, but had a long road of rehabilitation if it meant he was going to play baseball again. After grueling months spent relearning simple tasks like how to tie his shoes, Westmoreland made it almost all the way back, playing in a Dominication instructional league game in December 2011. 

However, a second malformation was found in July 2012, this one bleeding. He was deaf in his right ear and blind in his left eye, resulting in his retirement the following March. His number has since been retired by the Lowell Spinners, and he has been the subject of highly recommended features on ESPN's E:60 and on NESN, and was profiled this past March in the Boston Globe. Most importantly, after 17 brain surgeries, Westmoreland continues to live his life.

Final thoughts
The draft was not filled with high-end talent, but it managed to send nine players to the big leagues, including one that is still with the team. Even among those that did not sign, there was plenty of big league talent. The draft wouldn't bring any franchise-altering players or transactions, but did provide several role players, or pieces that would bring those players to Boston.

Photo Credit: Christian Vazquez, Tim Federowicz, Kyle Weiland, Stephen Fife and Ryan Westmoreland by Kelly O'Connor