With the 2010 Amateur Draft just around the corner (Monday June 7 through Wednesday, June 9), I wanted to spend this week’s column looking back at the previous best and worst picks of the Theo Epstein era, an era in which the strength of the minor league system has been both a top priority for the team and an area of almost unparalleled success.

With seven drafts under their belts, this front office has taken the team from a roster of two homegrown regulars (Nomar Garciaparra and Trot Nixon) in 2003 to eight in 2010. Among them are a perennial Cy Young contender, a powerhouse corner infielder, a league champion base stealer, an elite closer, a man with a 100 mile an hour fastball, and an MVP. In addition, there is a new crop of talent maturing in the minors, with some players nearing the point where they will make a Major League contribution. So, not bad for a few years. After the jump, we’ll take a look at the best and worst draft picks of the past seven years.

10. Luis Exposito, 2005 – 35th round, 948th overall pick
The first of three 2005 draftees on this list, Exposito was picked almost as an afterthought; even people who fall late due to signability don’t fall this far. Still, Exposito — now 23 and the regular catcher for the Portland Sea Dogs — has made a name for himself with both the bat and the glove. Last year, in his first stint in Portland, he posted an .860 OPS as a 22 year old catcher, forcing his way into the ‘catcher of the future’ conversation. His defensive skills are generally well-rated, and despite a 2007 suspension for undisclosed disciplinary reasons, he is well liked by teammates and coaches.

9. Ryan Kalish, 2006 – ninth round, 278th overall pick
Kalish is an anomaly: a lifelong Red Sox fan from New Jersey. Kalish fell to the ninth round due entirely to signability concerns, but decided against college in favor of playing for his preferred club when the Sox drafted him. Kalish is a big, athletic outfielder with speed, and both his offensive and defensive skills are at the top of the Sox system. With Ryan Westmoreland recovering from brain surgery, Kalish is the system’s top outfield prospect, and could be a natural Fenway left fielder.

8. Justin Masterson, 2006 – second round, 71st overall pick
Masterson was a bit of a surprise pick, and many believed he was a reach that high in the draft. Masterson proceeded to prove his critics wrong, and made an instant impression out of the Lowell bullpen, striking out 33 and walking just two in just under 32 innings. He was converted to a starter in 2007, and shot through the system, making his major league debut in 2008 and becoming a staple of the Red Sox bullpen. In 2009, he was the centerpiece, along with Nick Hagadone, in the deal for Victor Martinez.

7. Ryan Westmoreland, 2008 – fifth round, 172nd overall pick
Ryan Westmoreland is one of the more tragic stories in recent Sox memory. A Rhode Island native, Westmoreland was set to attend Vanderbilt on a full baseball scholarship when his hometown team drafted him. A five-tool player, Westmoreland looked like a star in the making, a center fielder who could run, field, and hit for both contact and power with a solid batting eye. He electrified everyone who saw him play, and his 2009 debut with the Lowell Spinners had people counting down the seasons until his Boston arrival. Then, this offseason, came the news that he had been diagnosed with a cavernous malformation in his brain, and would require surgery. A tricky procedure, the removal of the malformation carried no guarantee that Westmoreland would recover to full or near-full strength, and there has been no word on when — or whether — he will return to baseball.

6. Daniel Bard, 2006 – first round, 28th overall pick
Bard was in the middle of a starring turn on a championship College World Series UNC team when the Sox made him their second pick in the 2006 draft, behind high school outfielder Jason Place. He lit up radar guns during that series as a starter, and flashed an occasionally terrifying slider; the combination left most batters he faced helpless (or on first base — he suffered, and continues to suffer, from occasional wildness). The Sox converted him to a reliever early on in his minor league career, and after an abysmal first professional season between Greenville and Lancaster, he settled into his new role in 2008. Between Greenville and Portland that season, Bard struck out an astonishing 107 batters in just 77.2 innings, though walks continued to plague him in Portland. In 2009, after blowing away AAA competition (29 strikeouts and 5 walks in 16 innings), he earned a place in the Red Sox bullpen that he has not yet relinquished. Considered a future closer, he still has to refine his breaking stuff and avoid the occasional outbreak of wildness, but his raw talent is astounding.

5. Casey Kelly, 2008 – first round, 30th overall pick
Kelly was the rare two-way player in the minors; drafted for his pitching, Kelly preferred playing shortstop, and earned rave reviews for his defense, though his hitting left something to be desired. However, it was clear that he was something special on the mound: his first professional stint in Greenville saw him go 6-1 with a 1.12 ERA, 39 strikeouts, and nine walks in just over 48 innings. After the 2009 season, Kelly committed himself to pitching, and although he has struggled so far this season with AA Portland, at 20 years old he is clearly the top prospect in the organization and stands a strong chance of seeing playing time with the Sox in the next two seasons.

4. Jacoby Ellsbury, 2005 – first round, 23rd overall pick
With the first round pick from Anaheim (for Orlando Cabrera), the Sox grabbed center fielder Jacoby Ellsbury out of Oregon. Ellsbury, a lightning-fast baserunner, had drawn more than a few comparisons to then-Sox CF Johnny Damon; with Damon’s contract coming to an end after that season, Ellsbury was seen as a replacement down the line. However, no one could have guessed how quickly Ellsbury would arrive: showing tremendous patience, excellent contact, and blazing speed, he jumped three levels in his first two seasons. He began 2007 with a jaw-dropping 17 game stint in Portland hitting .452 with 10 doubles and an OPS over 1.150 before climbing through Pawtucket and onto the big club, where he hit .353 in 33 games. He earned a regular spot in 2008, and has since locked down the leadoff spot while setting both the single season rookie and regular season stolen base records for the Red Sox (50 and 70, respectively).

3. Clay Buchholz, 2005 – supp. first round, 42nd overall pick
Buchholz was in some ways a risky pick: a recently converted outfielder, there were no doubts about either his athleticism (he can, apparently, beat Ellsbury in a footrace) or his stuff, but there were many questions about his maturity after an incident of theft in college. Still, the Sox believed he’d outgrown any of those issues, and grabbed him with the third pick of their impressive 2005 draft. Buchholz did not disappoint, making his major league debut in 2007 after less than two years in the minors. In his second major league start, Buchholz authored a no-hitter against the Orioles. The following season, however, he struggled tremendously out of the gate, and there were rumors that the fame and attention had gone to his head. He came back at the end of 2009 a more mature and prepared pitcher, and has to this point in 2010 been the second best starter on the staff. Buchholz is a future ace or #2.

2. Jonathan Papelbon, 2003 – fourth round, 114th overall pick
A converted starter, Papelbon was drafted out of Mississippi State University in 2003. A later round pick, Papelbon had a rough first season with Lowell, but his stuff was good enough to earn a promotion to Sarasota in 2004. He spent the full season there, and it was good to him: a 2.64 ERA, with 153 strikeouts in just under 130 innings. 2005 saw him start at Portland, where he blew away AA competition, earning himself a rapid promotion to Pawtucket. After only a handful of games there, he was called up for a spot start in late July, and held his own against a tough Twins club in the middle of a swirling Manny-related media circus. He returned later that year as a reliever, and became an anchor for the bullpen down the stretch. When Keith Foulke faltered out of the gate in 2006, Papelbon was installed as closer, and became an instant sensation. After 2006, he was slated to move into the rotation, but decided during spring training to remain in the pen. He has been among baseball’s top closers — and dancers — since.

1. Dustin Pedroia, 2004 – second round, 65th overall pick
Who else? Pedroia, the little engine that not only could, but would then turn around and shove it in your face, is without question the finest draft pick of the Epstein era (note: Kevin Youkilis was drafted by Dan Duquette, Jon Lester in 2002 by interim GM Mike Port). Based on his height, he drew instant (and completely unfair) comparisons to David Eckstein early in his career. However, he quickly showed his advantages over Eckstein — among them patience, power, and an arm. He was a one-man army, grinding pitchers down at all levels of the minors. Arriving in Boston at the tail-end of the 2006 season, most expected him to continue his dominance; however he struggled badly. He was named the starting second baseman in 2007 as well, but began that season with an abysmal April before undergoing a complete transformation. He ended that season with a .317/.380.442 line and a Rookie of the Year award, and bettered his performance in 2008, walking away with an MVP trophy. At 26, he continues to improve and has become a team leader in addition to an offensive and defensive weapon.

Also of note here are Lars Anderson (the subject of an excellent piece here this Saturday), Michael Murphy, Will Middlebrooks, Anthony Rizzo, Jed Lowrie, and Aaron Bates.

And now for the biggest busts:

3. Jason Place, 2006 – first round, 27th overall pick
There’s still plenty of time for Place; a high school draftee, he has tremendous raw skills but has still not harnessed them, despite moving steadily up the system. His clubhouse reputation has some dark spots as well, and I’m not optimistic about his long-term potential. Neither, for the record, are either Baseball America or SoxProspects.com, both of whom ranked him quite low on the Sox top-prospects list.

2. Caleb Clay, 2006 – supp. first round, 44th overall pick
A high draft pick in a fairly strong 2006 draft, Clay fit the Buchholz mold: a converted OF with good stuff and a fresh arm. However, before he could get into any kind of a groove, he suffered a ligament injury in his pitching elbow and missed most of the 2008 season with Tommy John surgery. His 2009 season at Greenville saw his struggle with both velocity and control, and while his control has improved early this season, his results so far have not, as he has posted a 4.68 ERA with single A Salem.

1. Craig Hansen, 2005 – first round, 26th overall pick
Was there any doubt? Hansen was Daniel Bard before Bard was — a big, hard-throwing college closer, Hansen shot through the Sox system quickly (possibly too quickly), and arrived in Boston the same year he was drafted due to a shoddy bullpen. He had early success, but soon found too many of his pitches sailing over outfield walls. He bounced between Portland, Pawtucket and Boston for the next two seasons before getting shipped to Pittsburgh as part of the Jason Bay deal in 2008. He has been equally terrible for Pittsburgh in his limited time there, but has been sidelined this year due to a nerve problem and has yet to pitch.