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July 21, 2020 at 12:30 PM

2008 Draft Retrospective: The picks

We welcome you to the 2008 edition of the SoxProspects.com Draft Retrospective series. Over the next several weeks, we will revisit each draft going back to the start of the SoxProspects.com era. Each retrospective will come in two parts: The first will be a pick-by-pick recap of each selection with very brief comments, including their peak rank on the SoxProspects.com Top 60, as well as some of the notable players the team passed on to make those picks. Players who signed are in bold, those who did not are in italics. Bonus numbers are included where available.

The Red Sox won the World Series for the second time in four seasons in 2007, meaning the team would select at the end of each round. With young talent like Dustin Pedroia and Jonathan Papelbon and veterans including Daisuke Matsuzaka and Josh Beckett under team control for the foreseeable future, the team was largely ready to stand pat into the new season, not losing any picks to free agent signings. This left Theo Epstein and Co. a full stable of picks, including two compensatory selections, to stock the minor league system.

For a quick list and links to player pages, check out our Draft History page.

1 (30). Casey Kelly, RHP/SS Sarasota HS (Fla.)
Bonus: $2,631,000
Kelly (pictured, above) tore up area hitters as a high school senior and showed ability with the bat as well. While the club preferred him as a pitcher, the player preferred hitting, so the Red Sox came up with a unique development plan that allowed him to split his season between the two in 2009 (after only hitting after signing in 2008, mostly to rest his arm). He moved to the mound full-time for the 2010 campaign after having far more success as a pitcher the prior season, and the 20-year-old was challenged with an assignment to Double-A Portland. Kelly battled the level to a draw, posting a 5.35 ERA while striking out 81 in 95 innings, before he was dealt to San Diego along with Anthony Rizzo, Reymond Fuentes, and Eric Patterson to acquire Adrian Gonzalez. The right-hander struggled in the major leagues through 85 2/3 innings between 2012 and 2018, with a Tommy John surgery in 2013 for good measure, Kelly has found greater success abroad, carving out a role for himself for the LG Twins in the Korean Baseball Organization, where he is in his second season.
SoxProspects.com Peak Rank: 1
Baseball America Top 100: 24 in 2010; 31 in 2011; 76 in 2012; 45 in 2013
MLB.com Top 100: 50 in 2012; 69 in 2013; 87 in 2014
Notable players passed on: Jake Odorizzi (32), Conor Gillaspie (37), Lance Lynn (39)

1s (45). Bryan Price, RHP, Rice
Bonus: $849,000
Selected with a compensation pick for losing Eric Gagne to free agency, Price had a low-mileage arm after having thrown just 65 2/3 innings during his college career, a type of player that was popular with Epstein and McLeod. He spent barely over a year in the system, as the 6-foot-4 right-hander was part of the deal at the 2009 trade deadline that brought Victor Martinez to Boston from Cleveland. Price threw 2 2/3 innings across three appearances in 2014 for the Indians, but would not pitch in the major leagues again.
SoxProspects Peak Rank: 9
Notable players passed on: Logan Forsythe (46), Brad Hand (52)

2 (77). Derrik Gibson, SS, Seaford HS (Del.)
Bonus: $600,000
A two-time Gatorade Player of the Year in Delaware, Gibson earned a second-round selection and rose steadily up the minor league ladder. With a good plate approach and athleticism but slender build that limited his power, Gibson parlayed a good 2009 with Lowell into a top-20 ranking and earned a spot in the Arizona Fall League after the 2013 season, but he topped out at Triple-A where he spent parts of five seasons. Gibson's best year came in 2014, when he hit .302/.390/.395 for Portland, but he scuffled some after an August promotion to Pawtucket and he departed as a minor league free agent that winter. He bounced between the Orioles, Mets, and Rockies between 2015 and 2018.
SoxProspects.com Peak Rank: 15

3 (85). Stephen Fife, RHP, Utah
Bonus: $464,000
Selected with the compensation pick for failing to sign Hunter Morris in 2007, Fife never really matched the success of his first full season in 2009, in which he had a 3.71 ERA across Low and High A, goosed up mostly by eight strong starts in Greenville before a promotion to Salem. In his second season at Double-A Portland in 2011, he was dealt at the trade deadline as part of the three-way trade with the Mariners and Dodgers that brought Erik Bedard to Boston, part of alleviating a logjam of Rule 5-eligible players—many of them from this draft. The right-hander with a solid, 6-foot-3 frame was an up-and-down player for the Dodgers for the next three seasons before missing the 2015 season. He later appeared in the Cubs, Marlins, and Indians organizations and spent 2017 in Japan with the Seibu Lions.
SoxProspects.com Peak Rank: 15

3 (108). Kyle Weiland, RHP, Notre Dame
Bonus: $322,000
Weiland was the third tall, right-handed college pitcher the Red Sox selected with their first five picks and the third the team traded away. After dominating Lowell, he jumped right to High A Salem in his first full season and held his own, posting a 3.46 ERA and getting by mostly on pitching to contact. A steady rise through the farm system led to his making his MLB debut for the Sox in 2011, making seven appearances, five starts, over two stretches with the club. The Notre Dame product was packaged with Jed Lowrie and sent to Houston in exchange for Mark Melancon during the 2011 offseason and threw 17 2/3 innings for the Astros in 2012 before being shut down with a shoulder injury. An MRI showed no structural damage, but what was initially diagnosed as bursitis that required arthroscopic surgery was determined to be a rare infection that shut him down or the season. A recurrence kept him out until 2014, when he pitched only 17 innings.
SoxProspects.com Peak Rank: 6

4. Peter Hissey, CF, Unionville HS (Pa.)
Bonus: $1,000,000
An athletic center fielder whose strongest tools were his speed and defense, Hissey commanded a big bonus to forgo his commitment to Virginia. Hissey struggled to hit at the professional level but was a solid organizational player because of his strong defense and great makeup. He put together his strongest campaign at the plate in 2009 with Greenville, slashing .279/.356/.347, but plateaued over three years in Portland and became a minor league free agent after the 2014 season.
SoxProspects.com Peak Rank: 14

5. Ryan Westmoreland, CF, Portsmouth HS (R.I.)
Bonus: $1,604,000
A local product, Westmoreland (pictured, right) had one of the brightest futures of anyone selected by the Red Sox in the 2008 draft. He did not play for an affiliate after the draft so that he could rehab from surgery to repair a partially torn labrum, but burst on the scene in 2009 for Lowell. He slashed .296/.401/.484 and was on the fast track to garnering national attention, putting himself in the conversation as the system's top prospect (where he was ranked by Baseball America). However, after experiencing headaches and numbness, he was sent from Spring Training the following year to Mass General, where doctors discovered a cavernous malformation on his brain stem. Westmoreland would never suit up in a game again, undergoing multiple surgeries to remove that first cavernous malformation as well as a second years later. He made a heroic effort at returning to the game, even playing in a Dominican instructional league game in 2011 and suiting up in extended spring training, but was unable to return to organized baseball.
SoxProspects.com Peak Rank: 2
Baseball America Top 100: 21 in 2010

6. Ryan Lavarnway, C, Yale
Bonus: $325,000
After an epic minor league run that included twice winning SoxProspects.com Offensive Player of the Year, Lavarnway has carved out a long journeyman career for himself. The Red Sox drafted the Yale product after a 2008 season with a 1.365 OPS in the Ivy League, and the prowess with the bat showed throughout the minor leagues. Save for his 71 at-bats in Lowell in his draft year, the native Californian had an OPS above .800 and a batting average above .275 at each stop, moving quickly through the system. Lavarnway's defense drew mixed reviews, as there were significant questions about his ability to stick at catcher, but his bat continued to carry him. In an outstanding 2011 season split between Portland and Pawtucket, he hit .290/.376/.563 with 32 homers and earned the call to the majors on August 18. Lavarnway played well enough to get the start for the last three heartbreaking games of that season, hitting two homers in the penultimate contest that kept the team tied for the wild card spot. His star fell over the next three years as his bat finally met its match in Major League pitching, and he was designated for assignment following the 2014 season. He has been included in the 60-man player pool for Miami, his 11th major league organization.
SoxProspects.com Peak Rank: 4
MLB.com Top 100: 93 in 2012

7. Tim Federowicz, C, North Carolina
Bonus: $150,000
Federowicz is another catcher that has shuffled around between organizations throughout his career,  including as a member of the player pool for Texas for 2020, his sixth team since leaving Boston. His profile was opposite of Lavarnway's in that he was much more proficient behind the plate but faced questions about how he would profile in the batter's box. So strong was his defensive profile that at least one national writer speculated he might be recalled to the Major Leagues from Salem in 2010 down the stretch as a late-inning defensive replacement (although it is not clear that this was ever considered by the club). Federowicz was in the midst of a solid year in Portland when he was sent to the Dodgers along with fellow 2008 draftee Stephen Fife in the three-way trade that brought Erik Bedard to Boston in 2011. Federowicz would make his major league debut for Los Angeles that September.
SoxProspects.com Peak Rank: 12

8. Mike Lee, RHP, Oklahoma City University
Bonus: $100,000
The NAIA product stood at 6-foot-7 and had a fastball that reached 89 mph. Lee pitched to contact, but once he got to Portland, he struggled to get batters out. Although we speculated he might see more success in a bullpen role, he was released in April 2012 before getting a look as a reliever. He caught on with the Braves' organization later in the year and also spent time in the Arizona and Toronto systems.

9. Christian Vazquez, C, P.R. Baseball Academy (P.R.)
Bonus: $80,000
By any measure, Vazquez (pictured, left) is the star of this draft, incredible to think about considering his relatively meager bonus compared to his fellow draftees and inauspicious beginnings as a pro. First, he was assigned to repeat the GCL to start the 2009 season, historically a terrible sign for a draftee's MLB potential. Fast-forward 11 years following a slow, steady climb up the ladder, during which he established himself as a good defensive catcher with a superlative arm and was an All-Star in the Carolina League, Eastern League, and International League in addition to playing in the Futures Game, and Vazquez is the only player in the organization remaining from the draft and the longest-tenured Red Sox currently with the club in Boston (i.e., other than Dustin Pedroia. According to Baseball Reference, Vazquez has been worth 2.9 wins above replacement through his career and was a 2.3-win player in 2019, when he really came on at the plate to complement his strong defensive ability, particularly his arm. After signing a contract extension during camp in 2018, he will likely be a fixture in Boston's lineup through at least 2022.
SoxProspects.com Peak Rank: 9

10. Pete Ruiz, RHP, Santa Barbara CC
Bonus: $100,000
The first junior college player off the board for the Red Sox had a fastball that sat in the low 90s paired with a very good curve. His career jumpstarted with a move to the bullpen in 2012, as he posted a 3.14 ERA with Salem and earned an invite to the Arizona Fall League. He returned to Arizona after a 2013 in which he allowed a 5.23 ERA with Portland but struck out 69 in 53 1/3 innings. He was not re-signed after injuries limited him in 2014. Ruiz also can do a tremendous Tim Kurkjian impression and teammate Anthony Ranaudo uploaded the bit to YouTube, garnering more than 62,000 views and an appearance on Baseball Tonight.
SoxProspects.com Peak Rank: 47

11. Bryan Peterson, OF, West Valley HS (Wash.)
Peterson had a strong debut after being drafted, slashing .277/.361/.394 in 137 at-bats in the Gulf Coast League. However, he was unable to recapture the magic in either of the next two seasons and played sporadically due to injury, garnering just 125 at-bats over the rest of his career. Peterson was released prior to the 2011 season.
SoxProspects.com Peak Rank: 41

12. Lance McClain, LHP, Cumberland University
A pure reliever, McClain did not throw hard, but had good pitchability, compiling a 3.69 ERA in 87 appearances over three seasons.
SoxProspects.com Peak Rank: 45

13. Tyler Wilson, RHP, Armuchee HS (Ga.)
Bonus: $300,000
A big, 6-foot-6 right-hander, Wilson was a soft-throwing pitcher who spent four years as a staple shuttling between Lowell and Greenville. He did not sign with another affiliated team after being released in March 2013, but he has played for several independent teams, most recently with the Cleburne Railroaders of the American Association. He was one of two Tyler Wilsons pitching for the Red Sox during Spring Training 2010.
SoxProspects.com Peak Rank: 43

14. Tyler Yockey, CF, Acadiana HS (La.)
Bonus: $135,000
Yockey was a big, athletic outfielder with an aggressive approach. He showed flashes of power but contact was an issue, as he struck out 75 times in 181 plate appearances across two seasons in the Gulf Coast League. He was released prior to the 2010 season.

15. John Lally, LHP, Santa Margarita HS (Calif.)
The first draftee that did not sign, Lally instead attended Loyola Marymount in Los Angeles and was not re-drafted.

16. Mitch Herold, LHP, UCF
A groundball pitcher, Herold had solid seasons in the lower minors and reached as high as Portland. His best season came in 2009, as the lefty stymied South Atlantic League hitters with a 1.92 ERA and 71 strikeouts in 65 2/3 innings.
SoxProspects.com Peak Rank: 48

17. Jordan Cooper, RHP, Shawnee Heights HS (Kan.)
Cooper elected to attend Wichita State instead of signing with the Red Sox. A draft-eligible sophomore, he was selected by Cleveland in the ninth round of the 2010 draft and made it as high as Triple-A with the Indians, but never got the call to the big leagues.

18. Brian Flynn, LHP, Owasso HS (Okla.)
Flynn also would attend Wichita State and improve his draft position, going to Detroit in the seventh round of the 2011 draft. He made his debut in 2013 with Miami and has pitched 187 2/3 innings across his major league career, worth 0.9 WAR. He is currently in the Texas Rangers' system.

19. Brian Humphries, CF, Granite Hills HS (Calif.)
Humphries opted to attend Pepperdine rather than sign with the Red Sox. He was drafted by Colorado in the 14th round of the 2011 draft and was released in 2014 after reaching Double-A.

20. Alex Meyer, RHP, Greensburg HS (Ind.)
The Red Sox tried extremely hard to court the Indiana product, reportedly offering as much as $2.2 million, but he would not sign on the dotted line. Instead, Meyer became a first-round pick of the Washington Nationals in 2011 after three years at Kentucky. The six-foot-nine monster struggled at times to control a fastball that sat comfortably in the mid-90s, but his tremendous upside was recognized with four appearances on the MLB.com Top 100 list. He was dealt to the Twins following the 2012 season in exchange for Denard Span and reached the majors in 2015. A torn laburm suffered in late 2017 proved to be career-ending, and Meyer officially retired in 2019.

21. Jon Hee, 2B, Hawaii
Hee was a solid organizational player with a plus glove between 2008 and 2013, retiring early in the 2013 season. His best season came in 2011 with Portland when he hit .275/.362/.390 and started at least 10 games at all four infield positions. 

22. Anthony DeSclafani, RHP, Colts Neck HS (N.J.)
The Red Sox could not get the highly-regarded DeSclafani to sign away from his commitment to Florida, and Toronto made him a sixth-round pick in the 2011 draft. He made his major league debut with Miami and was traded to Cincinnati prior to 2014. He has been a solid part of the Reds' rotation since, accumulating 6.6 WAR over his major league career despite missing the 2017 season.

23. Seth Garrison, RHP, TCU
A big Texas-born right-hander, Garrison signed this time after electing to return to school in 2007. He had a solid 2009 with Greenville, but missed most of 2010 and was unable to regain his form. Garrison retired after the 2011 season.
SoxProspects.com Peak Rank: 49

24. Ricky Oropesa, 1B, Etiwanda HS (Calif.)
Oropesa, a highly regarded prep who would've required a large bonus, didn't sign and was later selected in the third round by San Francisco in 2011 after three years at USC. He would reach Triple-A, but his career ended following the 2016 season.

25. Justin Parker, LHP, Jesuit HS (Calif.)
Parker attended Consumnes River College instead of signing with the Red Sox. He was drafted again in 2010 in the 33rd round by Minnesota. He was released in 2011 after a 1.75 WHIP in the Appalachian League.

26. Navery Moore, RHP, Battle Ground HS (Tenn.)
Moore, another tough sign, was committed to Vanderbilt and as typical, particularly at this time, he went to Nashville to play for the Commodores instead of playing pro ball. Atlanta picked him in the 14th round of the 2011 draft, but did not get past High A before being released.

27. Hunter Cervenka, LHP, Sterling HS (Tex.)
Bonus: $350,000
Cervenka had completed three full, uneven seasons in the Red Sox organization, showing a high-quality cutter and fastball that touched 94 but struggling with walks and control issues. He was the player to be named later in the April 2012 trade that brought Marlon Byrd to Boston from the Cubs, and the change of scenery did him good. Cervenka had strong seasons in 2013 and 2014 in the Chicago system, but was cut after a difficult stretch at Triple-A Iowa in early 2015. After a short layover with the independent Sugar Land Skeeters, Cervenka hooked on with the Braves organization in July and made his major league debut the following spring. Between the Braves and Miami, has thrown 48 major league innings. He is currently in the Baltimore organization.
SoxProspects.com Peak Rank: 40

28. Matt Marquis, CF, Immaculata HS (N.J.)
Marquis opted to attend Maryland instead of coming to Boston out of high school, but would sign on the dotted line when the Red Sox came calling in the 41st round in 2011. More on his story when we reach that draft.

29. Jacob Rogers, 3B, Dunedin HS (Fla.)
Rogers attended Chipola College after not signing, transferring twice to St. Petersburg College (where he was drafted by the Cubs in the 44th round in 2010 but didn't sign) and the University of Mount Olive before signing as a 40th-round pick in the 2012 draft, again by the Cubs. He was converted to a pitcher with Texas in 2017, but was unsuccessful and has not played organized baseball since.

30. Alex Hale, RHP, Richmond
Hale was a senior sign out of Richmond. He pitched 7 2/3 innings for the Spinners in 2008 and was released before the 2009 season.

31. Andrew Frezza, OF, Barry
Frezza was one of two Barry alumni to sign with the Red Sox in this draft. He only had one professional season, slashing .263/.315/.381 in 118 at-bats with the GCL Red Sox. Currently, Frezza hosts the Seven Figure Box podcast and co-owns a CrossFit gym in Jupiter, Florida and has run several other small businesses since leaving baseball.

32. Travis Shaw, 3B, Washington Senior HS (Oh.)
Shaw (pictured, left) would end up coming to Boston three years later when the team selected him again, also in the 32nd round, after attending Kent State. We'll have more on him as part of the epic 2011 draft.
SoxProspects.com Peak Rank: 12

33. Brandon Miller, C, Woodward Academy (Ga.)
Miller would spurn the Red Sox for in-state Georgia Tech, but would transfer to a junior college before ending up at Samford, where Washington made him a fourth-round pick in 2012. Miller would make it to High-A before being cut in 2015.

34. Zak Sinclair, RHP, West Allegheny HS (Pa.)
Sinclair saw shine from Baseball America as young as 13 years old for already owning a fastball in the mid-80s. However, he did not sign with the Red Sox and suffered an arm injury in his freshman season at NC State.

35. Carson Blair, SS, Liberty Christian HS (Tex.)
Bonus: $200,000
Blair was moved to catcher before the 2009 season and become a solid option behind the plate as his glove improved. His bat also proved valuable once he settled into his new defensive position. He had his best year in 2014, slashing .288/.394/.525 in Portland, his first year at the level. The Red Sox did not re-sign him when his contract expired after that season and he would sign with Oakland, where he earned 31 major-league at-bats during the 2015 season. He also spent time in the Texas and White Sox organizations.
SoxProspects.com Peak Rank: 41

36. Richie Wasielewski, LHP, Brunswick Academy (Ga.)
Bonus: $135,000
Another big lefty, the six-foot-four Wasielewski threw in the low 90s, netting him a six-figure bonus. The Georgian would not make it out of the Gulf Coast League, throwing 30 professional innings across three seasons before being released after the 2010 season.

37. Tom Di Benedetto, SS, Trinity College
Di Benedetto played two seasons for the Red Sox and hit well in his second time at Greenville in 2009, slashing .308/.333/.462. His father, Thomas Di Benedetto, is a partner in Fenway Sports Group and also leads a group that owns Italian soccer club AS Roma.

38. John Hernandez, RHP, Barry
Hernandez was the second player selected from Barry by the Red Sox, though he did not sign and did not play affiliated baseball.

39. Yan Gomes, C, Tennessee
Perhaps one that got away for the Red Sox, Gomes was a draft-eligible sophomore at Tennessee. He would transfer to Barry after not signing and was selected by Toronto in the 10th round the following year. Gomes has accumulated 13.4 WAR since his major league debut in 2012 and was a 2018 American League All-Star, the only player selected by the Red Sox this year to have played in the Midsummer Classic. He was a key cog in Washington's World Series run in 2019 as well.

40. Sam Stafford, LHP, Klein Collins HS (Tex.)
The Red Sox could not pry Stafford away from his Texas commitment. The Yankees picked him in the second round in 2011, but did not sign him amid shoulder concerns revealed in a post-draft physical. He would sign with Texas when they picked him with a 13th-round selection in 2012. He would miss the 2012 season rehabbing from shoulder surgery and after two professional seasons, was released.

41. Dustin Mercadante, RHP, San Diego CC (Calif.)
With a high 80s fastball that had sinking action, Mercadante was a reliever for the GCL squad for two years before being released during Spring Training in 2010.

42. Caleb Brown, CF, Central Kitsap (Wash.)
Brown did not sign with the Red Sox and attended Washington. He was not drafted again.

43. John Killen, LHP, Blue Valley HS (Kan.)
Killen would end up at San Jacinto JC and sign with the Red Sox as an undrafted free agent in 2010. He pitched 21 innings across two years for the GCL Red Sox before his release in 2012. He ended up in the Kansas City system for one year before leaving organized baseball.

44. Bennett Whitmore, LHP, Fresno City College (Calif.)
Whitmore was poised to join Oregon for the 2009 season and did not sign with the Red Sox. After transferring to Concordia-Irvine for his senior season, he was a 24th round selection of Seattle in 2010. He was released in 2011 after two seasons.

45. Jonathan Griffin, 1B, Manatee JC (Fla.)
Griffin chose not to sign and spent another year at Manatee before transferring to UCF. Arizona drafted him in the 21st round of the 2011 draft and he got as far as Double-A before being released.

46. Jeremy Heatley, RHP, North Lake CC (Tex.)
Instead of signing with the Red Sox, Heatley opted to head to Arkansas. The Marlins selected him in the 22nd round in 2010, where he would spend one year in Rookie ball before being released.

47. Jeremy Kehrt, RHP, Southern Indiana
Kehrt was a mainstay in the organization, spending nearly seven years pitching in a number of different roles and for every squad in the organization, including a stint in the Arizona Fall League.  The bulk of his time was spent in Portland, where he made 96 appearances over five seasons. Kehrt was traded to the Dodgers in exchange for cash in August 2014. He would also spend 2015 and 2016 with Los Angeles, but was cut prior to the 2017 season. He is now an area scout with the Arizona Diamondbacks.

48. Kevin Hoef, 3B, Iowa
Hoef opted to stay at Iowa for his senior season instead of going pro and was not re-drafted. He was a member of the Roswell Invaders during the Pecos Baseball League's inaugural 2011 season.

49. Zach Gentile, 2B, Western Michigan
The diminutive Gentile was a fan favorite during his five years in the system, combining good contact skills with a high-energy style. His best campaign came in 2009 with Greenville, sporting a .281/.363/.340 slash line while moving around the infield. Gentile's versatility was a plus as he played every position except catcher and center field during his time in the system, even pitching an inning for Salem in 2011.

50. Kyle Stroup, RHP, Grant Community HS (Ill.)
Bonus: $150,000
Stroup's career was derailed by injuries, missing both the 2010 and 2012 seasons in their entirety, sandwiched by a very good year with Greenville in 2011. The big right-hander, for whom conditioning was occasionally a problem, posted a 3.67 ERA in 21 starts for the Drive, showing a fastball that would top out at 95. He struggled with his control upon his return in 2013 and a conversion to a bullpen role in 2014 was unsuccessful.


Raw Totals:
Players drafted: 52
Players signed: 29
Baseball America Top 100 prospects: 2
Signed players who reached majors: 9

Photo Credit: Casey Kelly, Ryan Westmoreland, Christian Vazquez, Travis Shaw by Kelly O'Connor