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The Theo Epstein years: The good, the bad and the ugly transactions

Posted by Peter Abraham, Globe Staff  October 12, 2011 03:21 PM

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Theo Epsteinís first transaction as general manager of the Red Sox was signing lefthanded reliever Steve Woodard on Nov. 25, 2002. His last was acquiring 1B/OF Conor Jackson from Oakland for righthanded reliever Jason Rice and cash on Aug. 31, 2011.

During his nearly nine years on the job Epstein made hundreds of deals. Some worked out and others didnít. Hereís a breakdown of the more memorable ones.

FREE AGENTS
Finds
DH David Ortiz (2003, 1 year, $1.2 million)
INF Bill Mueller (2002, 2 years, $4.5 million)
RHP Keith Foulke (2004, 3 years, $20.2 million)
LHP Hideki Okajima (2006, 2 years, $2.5 million)
RHP Takashi Saito (2009, 1 year, $1.5 million)
3B Adrian Beltre (2010, 1 year, $9 million)
RHP Alfredo Aceves (2011, 1 year, $650,000)

Busts
SS Edgar Renteria (2004, 4 years, $40 million)
RHP Matt Clement (2004, 3 years, $25.8 million)
SS Julio Lugo (2006, 4 years, $36 million)
RHP Daisuke Matsuzaka (2006, 6 years, $52 million plus $51 million posting fee)
RHP Brad Penny (2008, 1 year, $5 million)
RHP John Smoltz (2009, 1 year, $5.5 million)
RHP John Lackey (2009, 5 years, $82.5 million)
OF Mike Cameron (2009, 2 years, $15.5 million)
RHP Bobby Jenks (2010, 2 years, $12 million)

Mixed reviews
LHP David Wells (2004, 2 years, $8.1 million)
OF J.D. Drew (2007, 5 years, $70 million)
SS Marco Scutaro (2009, 2 years, $12.5 million)

Too soon to tell
OF Carl Crawford (2010, 7 years, $142 million)

TRADES
Good swaps
1B Kevin Millar for cash (2003, from Marlins)
RHP Scott Williamson for two prospects (2003, from Reds)
RHP Curt Schilling for four prospects (2003, from Diamondbacks)
INF Mark Bellhorn for one prospect (2003 from Dodgers)
1B Doug Mientkiewicz and SS Orlando Cabrera for SS Nomar Garciaparra and OF Matt Murton (2004 with Twins and Expos)
OF Dave Roberts for OF Henri Stanley (2004 from Dodgers)
OF Jason Bay for OF Manny Ramirez, RHP Craig Hansen and OF Brandon Moss (2008 with Pirates and Dodgers)
SS Alex Gonzales for a prospect (2009 from Reds)
C Jarrod Saltalamacchia for three prospects (2010 from Rangers)
1B Adrian Gonzalez for three prospects (2010 from Padres)

Bad swaps
OF Wily Mo Pena for RHP Bronson Arroyo (2006 from Reds)
C Doug Mirabelli for RHP Cla Meredith and C Josh Bard (2006 from Padres)
RHP Eric Gagne for OF David Murphy and two prospects (2007 from Rangers)

Mixed reviews
RHP Byung-Hyun Kim for INF Shea Hillenbrand (2003 from Diamondbacks)
C-1B Victor Martinez for RHP Justin Masterson and two prospects (2009 from Indians)

CONTRACT EXTENSIONS
Good deals
RHP Tim Wakefield (2006, 1 year, $4 million with recurring options)
DH David Ortiz (2004, 2 years, $12.5 million)
RHP Josh Beckett (2006, 3 years, $30 million)
2B Dustin Pedroia (2008, 6 years, $40.5 million)
3B Kevin Youkilis (2009, 4 years, $41.13 million)
LHP Jon Lester (2009, 5 years, $30 million)

Bad deals
OF Coco Crisp (2006, 3 years, $15.5 million)
RHP Joel Piniero (2007, 1 year, $4 million)
RHP Curt Schilling (2007, 1 year, $8 million)
3B Mike Lowell (2007, 3 years, $37.5 million)

Too soon to tell
Josh Beckett (2010, 4 years, $68 million)
Clay Buchholz (2011, 4 years, $29.95 million)
Adrian Gonzalez (2011, 7 years, $154 million)

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