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October 15, 2011 at 5:31 PM

Theo's best and worst draft 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.

Check out the full column on ESPN Boston