Considering that my former post on this topic is getting some attention, I’ll post a followup:
Drafting
This has been consistently Theo’s strongest area. No one can argue with the depth that Epstein has built in our farm system, especially compared with the Dan Duquette era. He’s been incredible at using free agent compensation to our advantage, and his scouting team always hits at least once a year. We have a lot of good, up-and-coming pitchers, and some good depth overall. We do lack power bats in the system, especially in the outfield.
2003
Jonathan Papelbon (++) Taken with the 114th pick. Amazing.
Matt Murton (+) Now a solid outfielder for the Cubs.
David Murphy (-) Not a great return for a first-rounder.
Abe Alvarez (-) Second-round pick hasn’t really panned out.
2004
Dustin Pedroia (++) Was their first pick at 65. And what a pick.
Andrew Dobies (-) Who?
2005
Jacoby Ellsbury (++) From what we’ve seen so far, he’s awesome.
Clay Buchholz (++) More than enough compensation for Pedro.
Michael Bowden (+) A very good pitching prospect in our system.
Jed Lowrie (+) A pretty good midle infield candidate.
Craig Hansen (0) Could still pan out, but we’re still waiting.
2006
Lars Anderson (++) A steal for where he was drafted.
Jason Place (+) A little early to say, but he’s one of the few power-hitting outfielders in our system.
Daniel Bard (+) A fireballer in our farm system.
Justin Masterson (+) Shown signs of being a good one.
Aaron Bates (+) Gives us good depth at 1B.
Bryce Cox (+) Another power arm for the pen.
Caleb Clay (0) Played well in his first short year.
Kris Johnson (0) A great first year followed by a bad one in Lancaster.
2007
Nick Hagadone (+) Has looked good thus far.
Free agents
Free agent signings are notoriously difficult, and probably the part where Epstein has faltered most often. What enrages many fans is that many players sign for big bucks, then come here and struggle (at least initially).
2002-2003
David Ortiz (++) No one could have guessed what he’d become, not even Theo.
Mike Timlin (++) Has been a mainstay in our bullpen ever since.
Bill Mueller (+) He won a batting title and was very solid when healthy.
Kevin Millar (+) Claimed off of waivers, the original cowboy contributed pretty well.
Bronson Arroyo (+) Claimed off of waivers and was a great teammate.
Chad Fox (0) Not expensive, and he pitched like it. Released in July.
Ramiro Mendoza (-) Terrible first year, released in his second year.
2003-2004
Keith Foulke (+) Only the way things ended keep this from being two pluses.
Pokey Reese (0) Personally don’t think his defense was so great, but he didn’t hurt.
Ellis Burks (-) Earned $750k for 33 major league ABs.
Curtis Leskanic (-) Blech.
2004-2005
John Olerud (+) I’m a fan, what can I say?
David Wells (0) Love him or hate him, he was okay.
Edgar Renteria (-) One of the most controversial signings, we was traded in one year.
Wade Miller (-) Low risk contract, but didn’t work out.
John Halama (-) Didn’t provide much.
Matt Mantei (-) Never worked out.
Matt Clement (- -) Probably the worst of the signings.
2005-2006
J.T. Snow (+) I thought he was a great signing.
Julian Tavarez (+) As much as I disliked him, he deserves a lot of credit for this year.
Alex Gonzalez (0) His defense dazzled, and he (sometimes) wasn’t abysmal at the plate.
Tony Graffanino (0) Even.
2006-2007
Hideki Okajima (++) This “hero in the dark” surprised everyone.
Daisuke Matsuzaka (+) Was in line for RoY until fall collapse; will bounce back.
Bobby Kielty (+) This pissed off Brady Clark, but Kielty’s been a great role player for us.
Julio Lugo (-) Another year, another struggling shortstop. He could still make it up.
J.D. Drew (- -) 5 years, $70 million. Probably the biggest disappointment on this year’s team.
J.C. Romero (- -) Maybe we should just avoid guys with double initials from now on.
Joel Pineiro (- -) The most expensive mopup guy of 2007.
Extensions
Kind of similar to free agent signings, only you know more what you’re getting. So you’d better be on the ball with these. And Theo has been, for the most part. He also has never gone to arbitration with ANYONE in his time with the Red Sox, which shows some of his diplomacy with the young players.
2004-2005
Jason Varitek (+) 4 years, $40M and worth every penny.
2005-2006
David Ortiz (++) 4 year extension WAY below market value.
Josh Beckett (++) 3 year extension below his worth as well.
Tim Wakefield (++) His perpetual $4M team option is a thing of beauty for the team.
Coco Crisp (+) 3 years at $15.5M makes him very tradeable, just watch this offseason.
2006-2007
Alex Cora (+) Is a very good utility infielder and mentor for other players.
Mike Timlin (+) Having him here another year, even hurt, was satisfying to a lot of fans and players.
Doug Mirabelli (0) He needs to go next season, sorry.
Trades
Trades take years to figure out if they were good or not, but here’s what we can say.
2002-2003
Josh Thigpen and Tony Blanco for Todd Walker (+) Produced well in his one season for the Sox.
Rene Miniel for Lou Merloni (+) At least Lou was a fan favorite.
Javier Lopez for Ryan Cameron (0) Not an impact trade.
Tyler Pelland for Scott Williamson (0) Even Steven.
Shea Hillenbrand for Byung-Hyun Kim (0) I’ll call it even, since Kim contributed a little, and so did Shea.
Josh Hancock for Jeremy Giambi (-) Hardly played and wasn’t good when he did.
Luis Cruz for Cesar Crespo (-) Yuck. Good thing he wasn’t expensive.
Freddy Sanchez, Mike Gonzalez for Jeff Suppan, Brandon Lyon, Anastacio Martinez (- -) Lost two very good youngsters and didn’t gain much back.
2003-2004
Casey Fossum, Brandon Lyon, Jorge de la Rosa and Michael Goss for Curt Schilling (++) A bloody good steal for the Sox.
Nomar Garciaparra and Matt Murton for Orlando Cabrera and Doug Mientkiewicz (++) Took a lot of guts, but it paid off big time.
Henri Stanley for Dave Roberts (+) You don’t do this deal, you don’t beat the Yankees in the ALCS.
for Mark Bellhorn (+) A key cog for that magical postseason.
for Mike Myers (+) Without him, the bullpen is lefty-less.
John Hatti for Terry Adams (0) You gotta give something to get something.
2004-2005
Ramon Vazquez for Alex Cora (++) Never was there a more unbalanced swap of utility players.
Dave Roberts for Jay Payton, Ramon Vazquez and David Pauley (+) A very good deal for the Sox.
Doug Mientkiewicz for Ian Bladergroen (+) Flipping a defenseman for a pretty decent prospect is a nice move.
Carlos de la Cruz and Kevin Ool for Mike Myers (0) We keep wanting you back.
Byung-Hyun Kim for Chris Narveson and Charles Johnson (0) One of those 0 + 0 = 0 deals.
Chip Ambres and Juan Cedeno for Tony Graffanino (0) Graf was okay for a while.
Jay Payton for Chad Bradford (-) Never was there a more unbalanced one of these.
Olivo Astacio for Mike Remlinger (-) Shudder.
2005-2006
Hanley Ramirez, Anibal Sanchez, Jesus Delgado and Harvey Garcia for Josh Beckett, Mike Lowell and Guillermo Mota (++) Would’ve been nice to keep Hanley, but this was still worth it.*
Doug Mirabelli for Mark Loretta (++) A steal and a half.
Guillermo Mota, Andy Marte and Kelly Shoppach for Coco Crisp, David Riske and Josh Bard (+) This deal is still evolving, but seems to swing in our favor now.
Luis Mendoza for Bryan Corey (+) He’s been a good soldier and September callup for us.
David Wells for George Kottaras (0) Still waiting on this prospect to show up (figuratively, not literally).
PTBNL for Eric Hinske (0) Hinske’s been a solid veteran to have on the bench, but hasn’t contributed much.
David Riske for Javier Lopez (0) Which would I rather have? Neither, really.
Adam Stern for Javy Lopez (-) A desperate move which didn’t pay off.
Edgar Renteria for Andy Marte (- -) We’re still paying for this one, literally.
Bronson Arroyo for Wily Mo Pena (- -) It was the best of times, it was the worst of times.
Cla Meredith, Josh Bard and a PTBNL for Doug Mirabelli (- -) The Padres get even.
PTBNL for Jason Johnson (- -) The Indians should have been paying us to take him off their hands.
PTBNL for Jermaine Van Buren (- -) Seems to be a lot of these junk signings this year.
* not Theo’s call
2006-2007
Wily Mo Pena for Chris Carter (+) Not a terrible return for a player we didn’t need.
Phil Siebel for Brendan Donnelly (+) Provided necessary bullpen depth early on.
Joel Pineiro for a PTBNL (0) We’ll leave this one neutral until we see who we get in return.
Kason Gabbard, David Murphy and Engel Beltre for Eric Gagne (- -) There was no way to predict this trainwreck, really, but somehow Scott Boras always benefits.
Players Kept/Lost
One important aspect of a big market GM is knowing when to walk away from the negotiating table. You don’t sign a player because of his name, but based on what he can offer you for the length of the contract to come. Free agents who leave also have a nice side effect- compensatory draft picks.
2002-2003
Cliff Floyd (+) He went on to have an injury plagued 4 years with the Mets, but he was good when he played. Sox drafted Matt Murton and Abe Alvarez with the compensation picks.
Ugueth Urbina (+) No more All-Star years for Ugie, but he did sign for less money in Texas.
2003-2004
Todd Walker (+) An average hitter and pretty bad with the leather.
Brian Daubach (+) Essentially a replacement level player.
2004-2005
Pedro Martinez (++) People thought Theo was crazy. They thought wrong. This decision turned into Clay Buchholz and Jonathan Egan, so it’s real hard to argue against this.
Derek Lowe (+) Lowe has been pretty successful in the NL, where he belongs. Plus we got Craig Hansen and Michael Bowden out of it.
Kevin Millar (+) Can still get on base, but after some stopgap players, Youkilis has been an excellent replacement.
Orlando Cabrera (o) People still can’t figure out why we let him walk. At least we got Jacoby Ellsbury and Jed Lowrie with the comp picks.
2005-2006
Johnny Damon (++) It hurt for a year, but in retrospect a good call. We also drafted Daniel Bard and Kris Johnson with the comp picks.
Bill Mueller (++) He’s retired now, and we got Caleb Clay and Aaron Bates using the compensatory draft picks.
2006-2007
Keith Foulke (++) Good thing we let him go when we did, though he is planning a comeback. Netted us shortstop Ryan Dent.
Mark Loretta (+) No one remembers the stir it caused when we let him go because of Pedroia.
Trot Nixon (+) Not healthy enough to be a regular, and we have enough lefty outfield bats.
Lenny DiNardo (0) A fan fav, DiNardo was not going to do much here. He did have a good start against Boston this year.
Carlos Pena (-) Pena hit a lot of home runs this year for the Devil Rays. Who’d a thunk it? Not me.
Alex Gonzalez (-) Lugo did provide a little more offense, but not much. And he costs a lot more. We did get Nick Hagadone as compensation.
You can get a pretty comprehensive list of moves from Theo’s early years here.
Summary
I’d definitely say that Epstein struggled some early on, as he was learning the rules of the game. His free agent signings didn’t account for player makeup, or he projected players incorrectly, and that has cost the organization a lot of cash. But his team handles the business aspects very well, and drafts as well as anyone. Theo does have problems engineering trades sometimes, but who wants to trade with the big powerhouse team? It’s a tough task. Epstein has also made the right calls about when to let players go, except when it comes to acquiring one of his “dream” players (Renteria, Drew, Lugo, etc). Those have usually turned out to be nightmarish.
I think Epstein and Co. are getting smarter about the way they do business, and they are only getting better with experience. They’ll need everything they can muster, with the rest of the AL gunning for us from now on. That’s what happens when you win the AL championship.