Overall regular season record since 2004: 910-710 (.562)
Playoff Appearances: 6 (2004, 2005, 2007, 2008, 2009, 2013) 3 World Series Championships
Overall Free Agency Rating: 12 out of 20
Notable Long-term Contracts (3 years or more; doesn't include players who were re-signed)
Marco Scutaro, SS: Three years, $17M (2010-12)
Shane Victorino, OF: Three years, $39M (2013-15)
Julio Lugo, SS: Four years, $36M (2007-10)
Edgar Renteria, SS: Four years, $40M (2005-08)
Carl Crawford, OF: Seven years, $142M (2011-17)
Matt Clement, SP: Three years, $25M (2005-07)
Keith Foulke, RP: Three years, $18.75M (2004-06)
Not a ton of success in this area, although a handful of players, including Clement, J.D. Drew and Foulke, had some nice moments during their Red Sox stints. And Scutaro is on the list only because he lived up to expectations as a solid, yet unspectacular, option at shortstop.
Victorino is only one year into what many believed to be an overpay, but he was a Gold Glove winner in right field who had one of his best seasons at the plate. And he helped the team win a World Series. Barring a significant decline in production, his signing should go down as a good one.
Crawford was traded to the Dodgers less than two years into his deal, while Renteria was traded after one so-so season. The Sox would've loved to trade Lugo, but his lack of production made this a difficult task. They eventually traded him to St. Louis in the middle of his final year of the deal.
Notable Short-term Contracts (1-2 years; doesn't include players who were re-signed)
Mike Napoli (pictured), 1B: One year, $13M (2013)
Adrian Beltre, 3B: One year, $9M (2010)
Cody Ross, OF: One year, $3M (2012)
Koji Uehara, RP/SP: Two years, $8.5M (2013-14)
Bobby Jenks, RP: Two years, $12M (2011-12)
Joel Pineiro, RP: One year, $4M (2007)
Had the Red Sox kept Napoli's three-year, $39 million offer on the table last offseason, it would go down as a long-term contract success. Since he had to settle on a one-year deal after a degenerative hip condition was discovered, it will go down as one of the best short-term contracts in team history.
Beltre signed a one-year deal in order to boost his value after a poor 2009 season. It worked out great for both sides as Beltre had a .919 OPS, leading to a huge multi-year contract with Texas following the season. Ross did the same in 2012, posting an .807 OPS before landing a three-year deal with the Diamondbacks.
Uehara would've still be a good signing had he been a setup man the entire season. His rise to the closer's role after season-ending injuries to Joel Hanrahan and Andrew Bailey makes it one of the best values in recent history.
Aside from Uehara, the Sox haven't had great luck with free agent relievers. Ramiro Mendoza, J.C. Romero and Julian Taveras were all busts. But Pineiro is in a different class while Jenks, who had a 6.32 ERA in 15.2 innings for the Sox before a string of injuries ended his career, goes down as the worst.
Pineiro was brought in to be the team's closer so Jonathan Papelbon could move into the rotation, but those plans were scrapped before the season started. After struggling in a middle relief role during his short stint in Boston, Pineiro was traded, along with cash, in July.
Notable Re-signings/Contract Extensions
Jason Varitek, C: Four years, $40M (2005-08)
David Ortiz, DH: Two years, $12.5M (2005-06); Five years, $64.5M (2007-11); One year, $14.575M (2012); Two years, $26M (2013-14);
Adrian Gonzalez, 1B: Seven years, $154M (2012-18)
Dustin Pedroia, 2B: Seven years, $55M (2009-15); Six years, $85M (2016-21)
Jon Lester, SP: Six years, $42.75M (2009-14)
Josh Beckett, SP: Four years, $68M (2011-14)
Curt Schilling, SP: One year, $8M (2008)
The Sox have had their share of long-term contract flops, but they've done a terrific job keeping their stars in town. And players like Lester, Pedroia, Ortiz and Varitek have been a huge part of the team's success over the past decade.
Gonzalez may not have been living up to lofty expectation after signing his contract extension, but his value was still strong enough that the Dodgers took on two very bad contracts (Beckett, Crawford) and sent over two good prospects (Rubby De La Rosa, Allen Webster) to acquire him.
Notable Free Agent Departures
Victor Martinez, DH: Signed with Tigers for four years, $50M (2011-14)
Jason Bay, OF: Signed with Mets for four years, $66M (2010-13)
Cody Ross, OF: Signed with Diamondbacks for three years, $26M (2013-15)
Pedro Martinez, SP: Signed with Mets for four years, $53M (2005-08)
Jonathan Papelbon, RP: Signed with Phillies for four years, $50M (2012-15)
Adrian Beltre, 3B: Signed with Rangers for five years, $80M (2011-15)
Johnny Damon, OF: Signed with Yankees for four years, $52M (2006-09)
One of the keys to sustaining long-term success is to replace star players who have reached free agency and in line for risky, long-term deals for big money.
While re-signing Beltre and/or Damon would've been excellent moves, most players leaving Boston for big contracts haven't panned out for their new teams. And those that have, the Sox don't miss because they've gotten terrific production in their place.