The evolution of Red Sox drafts under Theo Epstein

"Baseball is a game of failure. Failure is inherent in everything in the game -- and the draft, probably more so than any aspect of our operation, is that way. You're going to miss on 38 out of 40 picks most years."
-- Theo Epstein

It's amazing the way the Red Sox seem to have figured out the draft.

Dustin Pedroia is the reigning American League MVP. Jacoby Ellsbury, Jed Lowrie and Justin Masterson are contributing at the big-league level. Clay Buchholz is the best pitcher in Triple-A. Lars Anderson, Ryan Kalish and Josh Reddick aren't far behind.

All of that's from one three-year span -- from 2004-06.

Yes, a good portion of the Anderson-Kalish-Reddick group of prospects will wash out before ever becoming impact major leaguers. And, yes, some of the Red Sox successes have come thanks to bonus demands they were willing to meet that small-market clubs were not. Still, though, it's far cheaper to make a mistake in the draft than to make a mistake in the free-agent market -- just ask the Royals, who passed on Evan Longoria in 2006 and Matt Wieters in 2007 but are paying Jose Guillen $12 million a season this year as well as next year. (The signing bonuses of Longoria and Wieters combined? $9 million.)

It hasn't always been that way, though. Here's a look back at the first six drafts of the Theo Epstein era in Boston:

2003
First round
17. David Murphy, OF
32. Matt Murton, OF
Murphy was dealt to Texas in the Eric Gagne deal; Murton was dealt to Chicago in the Nomar Garciaparra deal. Both have grown into serviceable but not exceptional big-league outfielders.
Still on the board: Chad Billingsley (24), Carlos Quentin (29), Adam Jones (37).

Later rounds
114. Jonathan Papelbon, RHP
"We had an area scout at the time, Joe Mason, who had done a good job identifying him, but he wasn't high on our radar screen," Epstein said. (Mason is now with the Brewers.) "A bunch of us went down to the SEC Tournament and saw him throw. It was a good combination of all the elements of choosing a player. Joe had done a good job on his makeup, we saw the velocity and the explosion on his fastball in person -- it was hard to miss -- and then putting the performance elements in play, too, with a guy with a really dominant strikeout-to-walk ratio in college.

"We took him, and I remember seeing him a couple of months later before a game in Lowell, and he was out there milking a cow. He had like a five and a half ERA, and he's out there before the game doing a ceremonial cow-milking, getting way too into it. It's like, 'What the heck did we draft here?' Sure enough, the next year, development got ahold of him and he went to a starting role in the Florida State League and was just beating hitters consistently with that explosive fastball in the zone and took off from there."

There's a secret to winning cow-milking contests, Papelbon said when asked about it this weekend.

"You've got to caress the nipple, man," he said.

2004
First round
No selection.

Later rounds
65. Dustin Pedroia, 2B
(Click here for the full story on that Pedroia pick.)

2005
First round
23. Jacoby Ellsbury
26. Craig Hansen
42. Clay Buchholz
45. Jed Lowrie
47. Michael Bowden

This one was epic. It's even tough to criticize the selection of Hansen despite the fact that Hansen, traded to Pittsburgh in the Jason Bay deal, seems close to washing out as a big-league pitcher. Most of the best players in that draft already were gone by that point -- Matt Garza went to Minnesota at No. 25, for example -- and the Red Sox still emerged with three more big-league players.

Later rounds
Catchers Mark Wagner (No. 288 overall, now in Double-A) and Luis Exposito (No. 948 overall, now in Single-A) also were plucked out of the later rounds. Both might have something to say about George Kottaras' job security in the next year or so.

But even when you have a draft that successful, there's always one that got away. The Red Sox chose high school catcher Jonathan Egan with their second-round pick, No. 57 overall, and missed out on future big-leaguers like Kevin Slowey, Yunel Escobar and Chase Headley. (Egan now is retired.)

"One guy Theo was really high on -- and I liked him, but not as much as him -- and where he was, looking back on the draft, ... one guy is Chase Headley," scouting director Jason McLeod said. "We were at that point in the draft where it was, 'I'm going to go for the upside!' and 'This guy can be a star!' Looking back, Headley is in the major leagues and has done everything that we, as a staff, probably thought he would do -- and (Epstein) really thought he was going to do. That's just one small example -- but you can do that in every draft and every round."

Said Epstein, "To be fair to Jason, the guy he really had to have in that draft was Buchholz. He was out on a limb on him."

2006
First round
27. Jason Place, OF
28. Daniel Bard, RHP
40. Kris Johnson, LHP
44. Caleb Clay, RHP

Place and Clay both were drafted out of high school and are working their way slowly through the system -- it's way too early to pass judgment on those picks. Johnson had a 3.63 ERA last season at Double-A Portland and pitched with the big-league club in spring training, but he's had a rough go of things so far this year at Triple-A Pawtucket. (The Yankees selected Joba Chamberlain with the No. 41 pick -- right after Johnson. There's one that got away.)

Bard, on the other hand, made his major-league debut last month and, while he's still living out of a hotel in Boston, he doesn't look like he's going to be sleeping in his own bed in Pawtucket again anytime soon. He has nine strikeouts and has allowed just one earned run in 10 big-league innings so far this season.

Later rounds
Second-round pick Justin Masterson already looks like the second coming of Derek Lowe. (As a side note, mark your calendars: Lowe is lined up to pitch at Fenway Park on June 20.) Third-round pick Aaron Bates (No. 83 overall) is mashing the ball at Double-A this season. Kalish (No. 283), Reddick (No. 523) and Anderson (No. 553) all are players the Red Sox expect eventually to contribute at the big-league level. If even one of those four pans out, it's an outstanding draft year.

2007
First round
55. Nick Hagadone
62. Ryan Dent

The Red Sox didn't have a first-round selection thanks to -- what else? -- the signing of Julio Lugo as a free agent. (Among the players still on the board when the Red Sox would have picked? Rick Porcello, the fast-moving righty who pitched against the Red Sox in Detroit this week.)

But they were pleasantly surprised -- as with Pedroia in 2004 -- to discover that Hagadone, who had a 72-to-17 strikeout-to-walk ratio as a junior at Washington, still was on the board in the supplemental first round.

"We didn't think Nick Hadagone would be at that pick just because of what he brought to the table -- lefthanded power arm and so forth," McLeod said. "We know every year is going to be different. Every team sees players different, so you have to be prepared as well as you can to make a decision."

Later rounds
First baseman Anthony Rizzo (No. 204) hit .373 with 11 home runs in 83 at-bats at Single-A Greenville before being diagnosed with lymphoma in 2008. He was declared cancer-free in November and is hitting .270 with six home runs and a .346 on-base percentage with Greenville so far this season.

2008
First round
30. Casey Kelly

Kelly is going to make the Masterson and Chamberlain starter-reliever debates look like child's play. Kelly came out of high school as a shortstop and a pitcher -- he prefers shortstop, but so far this season, he has a 1.35 ERA and 49 strikeouts in 60 innings on the mound. (He had a 1.12 ERA for Single-A Greenville and has allowed three earned runs in 11 2/3 innings since his promotion to Single-A Salem.)

Once he hits 100 innings on the mound -- which, counting spring training, will happen three or four starts down the road -- he'll switch to shortstop and play there for the rest of the season. Either way, he looks like a tremendous prospect.

Later rounds
Most of these players are just starting their first full season of pro baseball, but one early highlight has been catcher Tim Federowicz (No. 232), who's hitting .318 so far this season at Single-A Greenville.