A Trip Through Drafts Past

On Saturday, Cubs pitcher Kerry Wood decided to hang up his spikes and retire from baseball. It had been a bumpy road for Wood over the last decade, given the way he first appeared on the major league stage. Wood came up in 1998, and proceeded to strike out absolutely everyone. In his fifth game, the 21-year-old struck out 20 Astros, only the second pitcher to accomplish the feat. He finished the year with 233 strikeouts in 166.2 innings, winning Rookie of the Year. However, he missed all of September (yes, he struck out 233 batters despite missing a month) with an elbow problem that wound up needing Tommy John surgery.

Injuries would continue to be the story of Wood's career. He had several more dominant seasons with Chicago, but the innings racked up in those years finally took their toll. Wood spent most of the decade in a desperate battle to stay on the mound, mainly out of the bullpen. Even so, he's still one of only three men to average more than 10 K/9 for his career, along with Randy Johnson and Pedro Martinez. Looking back at Wood, you see a guy who should have been one of the all-timers, had his body (with a likely assist from Dusty Baker) not decided otherwise.

Why bring this up on a Red Sox blog? As usual, because nerdery took me down an odd path. While combing through Wood's stats over at Baseball-Reference (still the best website anywhere), I wound up looking at his draft class from 1995. Wood went fourth overall in the draft, in a first round that also featured Todd Helton and Roy Halladay. Boston had two picks, and used them on RHP Andrew Yount and OF Corey Jenkins. Neither of them ever saw major-league action. In fact, neither got above Single-A for Boston. Drafting, it turns out, is something of a crapshoot.

As these things do, one click led to another, and all of a sudden I was nine drafts in, and a column beckoned. So, for Monday morning, here's a journey through a decade of Boston's drafts from 1995-2005; who they drafted, who they could have drafted, and which player wound up producing most in a Boston uniform. It's a strange menagerie out there.

1995
Boston First-Rounders: Andrew Yount (RHP), Corey Jenkins (OF)
Notable First-Rounders: Kerry Wood, Todd Helton, Roy Halladay
Most Productive Boston Player: Paxton Crawford (1.0 WAR)

Yikes. For those of you who remember Paxton Crawford, the idea that he wound up being the most successful player Boston snagged is terrifying. Fun note: in the 43rd round, Boston snagged a HS third baseman named Pat Burrell. He didn't sign.

1996
Boston First-Rounders: Josh Garrett (RHP), Chris Reitsma (RHP)
Notable First-Rounders: Mark Kotsay, Eric Chavez, R.A. Dickey
Most Productive Boston Player: Shea Hillenbrand (4.7 WAR)

Yep, Shea Hillenbrand. Remember him? Even funnier, remember when we seriously thought there was a "who's the best rookie in the East" debate between him and Alfonso Soriano? Simpler times. Also in this draft, the Sox grabbed Justin Duchscherer, who never played for Boston, but did fetch us Doug Mirabelli in a trade with Texas.

1997
Boston First-Rounders: John Curtice (LHP), Mark Fischer (OF)
Notable First-Rounders: Troy Glaus, Vernon Wells, Lance Berkman
Most Productive Boston Player: Angel Santos (-0.3 WAR)

Yes, a draft even worse than 1995. No player drafted by Boston gave them any major-league value. Not a one. The Sox, did, however, draft a University of Florida second baseman who went on (after the Sox waived him) to produce 18.7 of the scrappiest, big-hearted-est WAR you ever did see: David Eckstein.

1998
Boston First-Rounders: Adam Everett (SS)
Notable First-Rounders: JD Drew, Carlos Pena, CC Sabathia
Most Productive Boston Player: Josh Hancock (0.2 WAR)

Adam Everett, of course, never played for Boston either, he wound up in Houston, traded for a different, more dinosaur-questioning Everett. In the ninth round, Boston picked a Baltimore HS third baseman who didn't sign. Apparently even at an early age, Mark Teixeira just really didn't want to play here.

1999
Boston First-Rounders: Rick Asadoorian (OF), Brad Baker (RHP), Casey Fossum (LHP)
Notable First-Rounders: Josh Hamilton, Josh Beckett, Barry Zito
Most Productive Boston Player: Casey Fossum (1.0 WAR)

It should be becoming clear at this point that Baltimore fans should not be expecting great things from Dan Duquette in terms of stocking their farm system. We're five drafts in, and still the most production Boston's seen out of a pick is from Fightin' Shea Hillenbrand. But Fossum did snag us Curt Schilling, which was good.

2000
Boston First-Rounders: Phil Dumatrait (LHP)
Notable First-Rounders: Adrian Gonzalez, Chase Utley, Adam Wainwright
Most Productive Boston Player: Manny Delcarmen (3.6 WAR)

Manny Delcarmen! Yeah, I got nothing. Although the Sox did get Freddy Sanchez, who played a little with Boston and wound up traded for Jeff Suppan. And eventually Boston did acquire Adrian Gonzalez. So there's that.

2001
Boston First-Rounders: None
Notable First-Rounders: Joe Mauer, Mark Teixeira, David Wright.
Most Productive Boston Player: Kevin Youkilis (28.9 WAR)

The Sox lost their first-rounder to Cleveland after signing Manny Ramirez. I'd say that turned out to be worth it. The Sox snagged Kelly Shoppach in the second round, but otherwise this draft was all Youk. The Sox also drafted Moneyball star Jeremy Brown, but he didn't sign.

2002
Boston First-Rounders: None
Notable First-Rounders: Zach Greinke, Cole Hamels, Matt Cain
Most Productive Boston Player: Jon Lester (22.7 WAR)

It was Johnny Damon who cost the Sox a pick here, with Boston's first-rounder going to Oakland and turning into Nick Swisher. Boston drafted Ricky Romero late, but again failed to sign. Lots and lots of nothing in this draft, but any draft that nabs you Jon Lester winds up in the win column.

2003
Boston First-Rounders: David Murphy (OF), Matt Murton (OF)
Notable First-Rounders: Nick Markakis, John Danks, Chad Billingsley
Most Productive Boston Player: Jonathan Papelbon (15.6 WAR)

Murphy went to Texas for Eric Gagne. *punches things* Murton was Chicago's free gift with purchase in the Nomar Garciaparra trade later that year. Boston took Pap in the fourth round. After that, they drafted no one who ever saw major-league playing time. Seriously, look. It's kind of eerie.

2004
Boston First-Rounders: None
Notable First-Rounders: Justin Verlander, Jered Weaver, Stephen Drew
Most Productive Boston Player: Dustin Pedroia (27.2 WAR)

Keith Foulke was the cause of Boston's lack of first-rounder here. Given that he traded his career for a Series win later that fall, I think we can accept the lack of draft pick. Besides, in the second round Boston selected a shortstop out of Arizona State, and he's turned out all right.

2005
Boston First-Rounders: Jacoby Ellsbury, Craig Hansen, Clay Buchholz, Jed Lowrie, Michael Bowden
Notable First-Rounders: Ryan Zimmerman, Ryan Braun, Troy Tulowitzki
Most Productive Boston Player: Jacoby Ellsbury (13.7 WAR)

It took ten years, but we finally found a productive first-rounder for Boston. Actually, a few of them. This was the draft that followed the post-2004 exodus of free agents, with Derek Lowe, Orlando Cabrera, and Pedro Martinez leaving and granting Boston their new team's draft picks. Incidentally, the entire 2005 draft was ridiculous. The aforementioned Zimmerman/Braun/Tulowitzki trio, along with Justin Upton, Alex Gordon, Andrew McCutchen, Jay Bruce, Ellsbury... Just a stacked first round.

So there it is, a decade of Boston drafts. A few gems late, a lot of lousy players early. There's a reason that Theo Epstein (and Ben Cherington after him) have always talked about creating a "player-development machine." When you draft well, it makes everything else easier and cheaper. Boston's latest crop of draft picks, especially Matt Barnes and Jackie Bradley, are looking good so far. The future may well be bright, and that's a nice change from the mid-nineties.