SoxProspects: Theo's best and worst picks

With Theo Epstein on the cusp of departing the Red Sox to join the Chicago Cubs organization, here’s a look at the best and worst draft picks of the Epstein era.

Best high-round picks (first, supplemental, or second round)

1. Dustin Pedroia -- Boston took the gritty second baseman out of Arizona State in the second round (64th overall) of the 2004 draft. He cruised through the minors and has since won American League Rookie of the Year and MVP honors, and is a three-time AL All-Star.

2. Jacoby Ellsbury -- The Red Sox selected Ellsbury out of Oregon State in the first round (23rd overall) in 2005. The 28-year-old outfielder is coming off of an MVP-caliber season in 2011. He could easily be listed at No. 1, but we’ll give Pedroia the nod as the best pick since he was a second-rounder.

3. Clay Buchholz -- Buchholz was snagged out of Angelina Junior College in the supplemental first round (42nd overall) in 2005. The right-hander dominated the minors and has gone 35-24 with a 3.64 ERA in 78 games with Boston.

4. Daniel Bard -- Boston picked Bard out of North Carolina in the first round (28th overall) of the 2006 draft. Originally projected as a starter, Bard had a horrific first minor-league season (3-7, 7.08 ERA) and was converted to the bullpen the following season. While there have been a few hiccups here and there -- this past September included -- he’s been one of the best relievers in the American League since his arrival to the majors in 2009.

5. Justin Masterson -- Masterson was selected out of San Diego State in the second round (71st overall) in 2006. Boston later packaged the big right-hander in a trade with Cleveland for catcher Victor Martinez in 2009. In 2011, Masterson went 12-10 with a 3.21 ERA in 34 games with the Indians.

Other solid high-round picks: David Murphy (1st round, 2003), Matt Murton (supplemental, 2003), Jed Lowrie (supplemental, 2005), Nick Hagadone (supp., 2007), Casey Kelly (1st round, 2008), Reymond Fuentes (1st round, 2009), Alex Wilson (2nd round, 2009), Bryce Brentz (supp., 2010), Antony Ranaudo (supp., 2010), Matt Barnes (1st round, 2011)

Best mid-round picks (3rd–10th rounds)

1. Jonathan Papelbon -- The Red Sox selected Papelbon out of Mississippi State in the fourth round of the 2003 draft. He has posted 219 saves in his seven-year major-league career, already placing him at No. 37 on the all-time saves list.

2. Anthony Rizzo -- Boston picked up Rizzo in the sixth round in 2007 out of Stoneman Douglas High School in Florida. He was traded with Kelly and Fuentes to San Diego for Adrian Gonzalez in December 2010. At just 22, Rizzo dominated Triple-A competition in 2011, putting up a .331/.404/.652 line with 26 home runs in 356 at-bats, but he struggled in a short major-league stint with San Diego.

3. Will Middlebrooks -- Middlebrooks was selected in the fifth round of the 2007 draft, coming out of Liberty-Eylau High School in Texas. The power-hitting third baseman is now considered the top prospect in the Red Sox system.

4. Ryan Kalish -- Epstein used his 2006 ninth-round pick to select Kalish out of Red Bank Catholic High School in New Jersey. In his six-year minor league career, Kalish has posted a .280/.367/.429 line, typically playing well above his age level. While his 2011 season was riddled with injuries, he still projects as an everyday outfielder at the major-league level.

5. Ryan Lavarnway -- The Red Sox drafted Lavarnway out of Yale in the sixth round of the 2008 draft. He has been the best hitter in the Sox system for three years running, putting up a minor-league career line of .284/.376/.521, showing remarkable plate discipline and power potential in the process. The 24-year-old backstop is slated for a permanent jump to the majors at some point in 2012.

Other solid mid-round picks: Cla Meredith (6th, 2004), Dustin Richardson (5th, 2006), Kyle Weiland (3rd, 2008), Ryan Westmoreland (5th, 2008), Tim Federowicz (7th, 2008), Christian Vasquez (9th, 2008), Jeremy Hazelbaker (4th, 2009), Brandon Jacobs (10th, 2009), Sean Coyle (3rd, 2010), Garin Cecchini (4th, 2010), Henry Ramos (5th, 2010), Cody Kukuk (7th, 2011)

Top late-round picks (11th–50th rounds)

1. Josh Reddick -- Selected in the 17th round of the 2006 draft, Reddick was the regular right fielder for the 2011 club and has a solid future as a third or fourth outfielder.

2. Drake Britton -- Boston picked up Britton, a lefty with a plus curveball and a mid-90s fastball, in the 23rd round in 2007. The 22-year-old had a poor season with High-A Salem in 2011, but still projects as a major league arm, whether it be a back-of-the-rotation starter or perhaps a high-leverage reliever.

3. Miles Head -- Head was drafted in the 26th round in 2009. He put up mediocre numbers in 2009 and 2010, but in 2011 the powerful first baseman hit .299/.372/.515 with 22 home runs in 495 at-bats between stops in Salem and Low-A Greenville.

4. Alex Hassan -- A Massachusetts native picked up in the 20th round in 2009 out of Duke, Hassan has shown an excellent plate approach at every level. In 2011, he hit .291/.404/.456 with 13 home runs for Double-A Portland. He likely projects as a fourth outfielder at the major league level.

5. Lars Anderson -- Once considered the top prospect in the organization, Anderson was drafted in the 18th round in 2006. While his stock has faded significantly in recent years, he still could have a future as a contributor at first base for a second-division club.

Other solid late-round picks: Luis Exposito (31st, 2005), Bubba Bell (39th, 2005), Kyle Stroup (50th, 2007), Dan Butler (undrafted free agent, 2008), Keith Couch (13th, 2010)

Worst draft picks

1. Jason Place -- Boston selected Place in the first round (27th overall) of the 2006 draft, and gave the prep outfielder a $1.3 million bonus, passing on players such as Joba Chamberlain, Chris Perez, Trevor Cahill and Zach Britton. Place went on to hit .230 over his minor-league career, never made it past Double-A and was released by the Red Sox in March 2011.

2. Mike Rozier -- After drafting Rozier in the 12th round in 2004, Boston gave him a $1.575 million bonus, one of the largest bonuses ever given out by the club to that point. The right-hander struggled with confidence and weight issues during his minor-league career, ultimately posting a 16-24 career record with a 5.23 ERA. He played in only one game above A-Ball during his career, and was released by the Red Sox in March 2009.

3. Jonathan Egan -- The Red Sox took Egan in the second round (57th overall) in 2005, and gave him a $625,000 bonus. He ran into some legal trouble early in his career, and after posting a .235 career batting average, the catcher was released in March 2008. He never played beyond Low-A Greenville.

4. Kris Johnson -- A left-hander out of Wichita State, Johnson was selected in the supplemental first round (39th overall) of the 2006 draft and given an $850,000 bonus. While he showed a few flashes of brilliance during his minor-league career, he was mostly mediocre and was released after putting up a 12.63 ERA in eight appearances with Pawtucket in 2011. Over his minor league career, Johnson was 28-49 with a 5.10 ERA.

5. Mickey Hall -- Boston selected Hall in the second round (54th overall) of the 2003 draft, passing on the likes of Andre Ethier, Scott Baker, Shawn Marcum and Drew Stubbs. The Sox traded Hall to Cleveland for Paul Byrd in 2008. He hit .234 over his minor league career, which ended following the 2009 season.

Other high-round picks that didn’t pan out: Abe Alvarez (2003, 2nd), Andrew Dobies (2004, 3rd), Craig Hansen (2005, 1st), Scott Blue (2005, 4th).

Other high-round picks that haven’t panned out (yet): Caleb Clay (2006, Suppl.), Ryan Dent (2007, Suppl.), Derrik Gibson (2008, 2nd), Peter Hissey (2008, 4th)

Draft picks who the Red Sox didn’t sign

1. Brandon Belt -- Boston drafted Belt as a prep pitcher in the 11th round in 2006, but failed to sign him. San Francisco then took him in the 5th round in 2009, and he has since gone on to become the top prospect in the Giants’ system as a first baseman. The 23-year-old made his major league debut in 2011.

2. Pedro Alvarez -- Alvarez headed to Vanderbilt after Boston was unable to sign him after selecting him in the 14th round in 2005. After three outstanding years with the Commodores, Pittsburgh took the third baseman with the second overall pick in 2008. While he hasn’t lived up to the expectations of a second overall pick to this point, he’s still only 24 and projects as an everyday third baseman over the long haul.

3. Yasmani Grandal -- Boston took Grandal, a Cuban catcher, in the 27th round in 2007, but was unable to sign him away from his commitment to the University of Miami. Cincinnati took him in the first round (12th overall) three seasons later. In two professional seasons, the backstop has hit .303/.401/.488 in the Reds’ system.

4. Matt LaPorta -- After the Red Sox failed to sign LaPorta after drafting him in the 14th round in 2006, the Brewers turned around and selected him in the first round (7th overall) the following season. While he’s had a mediocre major-league career to this point, he still has promise as an impact first baseman.

5. Hunter Morris -- Boston opted not to sign Morris because he changed his bonus demands after the Sox drafted him in the second round in 2007. He spent three years at Auburn, after which time Milwaukee picked him up in the fourth round of the 2010 draft. The first baseman has put up a .266/.303/.457 line in two seasons in the Brewers’ system.

Other draftees who didn’t sign with the Red Sox: Steve Pearce (10th, 2004), Jason Castro (43rd, 2005), Alex Meyer (20th, 2008), Sam Stafford (40th, 2008), Branden Kline (6th, 2009), Tyler Barnette (9th, 2010), Eric Jaffe (19th, 2010), Senquez Golson (8th, 2011)