The Red Sox turned an uncomfortable ballpark relic into a tourist attraction cash cow, stamped their brand across New England through their regional sports network ("the Nation Station") and in less than a decade transformed their national identity from century-long sad sacks into corporate profiteers. They have money -- lots of it -- but haven't always spent wisely. Investments in scouting and development enabled Boston to trade three of its top prospects to San Diego for Adrian Gonzalez, who looks like the AL MVP this season. The Red Sox then spent another $154 million to keep Gonzalez in Boston through 2018. Gonzalez, however, appears to be the exception and not the rule when looking at the current regime's history of personnel investments. A spotty record of free-agent signings has come back to bite Boston before and may again in 2011.
JOHN LACKEY -- 5 YEARS, $82.5 MILLION. To say he's been a disappointment would be an understatement. After a 14-11, 4.40 debut with Boston in 2010, Lackey has regressed. He's 9-8 with a 6.23 ERA and 1.55 WHIP. Opponents are hitting .303 against him. He's given up at least seven hits in 12 of his 18 starts, including seven of his past nine. Lackey's stuff is getting pounded. He's allowed 37 hits in 25 innings over his past four starts, but thanks to Boston's powerhouse offense Lackey is remarkably 3-0 in those four starts. His body language and mound hysterics when things go badly has been troubling and his near-total lack of effectiveness creates genuine concern about Boston's postseason rotation with Clay Buchholz possibly out for the season with a stress fracture in his back. Boston owes Lackey $15.25 million for each of the next three seasons after 2011.
J.D. DREW -- 5 YEARS, $70 MILLION. As a disappointing free-agent signing, Drew was Lackey's mirror image, but in terms of body language, his polar opposite; nothing fazed Drew. Red Sox fans were used to Kevin Youkilis slamming batting helmets or Trot Nixon toppling over right field walls. But there was Drew, seemingly unconcerned as he hit a parade of routine groundballs to second base, content to take ball four rather than swing away with a key run standing on second base, or out of the lineup again with another hamstring twinge. Red Sox fans accustomed to Sam Kinison's act at the Fenway Comedy Club instead got Steven Wright. Despite this, Drew has contributed. He's been an underrated defensive right fielder. His Boston résumé includes several clutch postseason hits, and his Wins Above Replacement with the Red Sox is 13.6. In 602 games in Boston, Drew has averaged .264 with 16 homers and 57 RBIs. His Red Sox OPS is .826. However, it's the $70 million figure and the placid exterior that will always define Drew's stay in Boston. He's batted just .219/.317/.305 in 77 games this season, creating a season-long search for another outfielder. In total, Drew's Red Sox contract may be a wash in terms of market value, but that doesn't change the fact that Boston has gotten almost nothing for its $14 million in this final year of the deal.
MIKE CAMERON -- 2 YEARS, $15.5 MILLION. When the Red Sox DFA'd Cameron on June 30, GM Theo Epstein could only tell The Boston Globe, "I'll take the hit on this one. When it doesn't work out you have to stand up and say that it didn't work out. We're not going to sugarcoat it." Cameron was signed prior to the 2010 season and given Jacoby Ellsbury's center-field spot, with Ellsbury shifting to left. The new outfield plan had to be scrapped almost as soon as it began. Ellsbury got injured and played only 18 games. Cameron would play in just 48. This season, Cameron looked every bit his 38 years of age, hitting .149 and finishing 3 for his last 38. Cameron and Drew were supposed to be a right-field platoon. Now Cameron is with the Marlins and Drew is injured, which has given Josh Reddick the chance for a breakthrough season. In this case, Boston's investment in player development filled a hole left by a failed decision to commit to Cameron.
BOBBY JENKS -- 2 YEARS, $12 MILLION. Jenks was supposed to be a key bullpen piece; the seventh-inning bridge to Daniel Bard in the eighth and then Jonathan Papelbon in the ninth. Jenks' experience as the White Sox's closer was also considered insurance should Papelbon struggle. Instead, Jenks has blown his two save opportunities and has a 6.32 ERA and 2.23 WHIP in just 19 appearances. He's currently on the DL with a mid-back injury, for which he had a cortisone shot on July 28. Jenks' washout has left a hole in the Boston bullpen that still hasn't been filled. The Red Sox had other middle-relief options this winter. Jesse Crain got three years, $13 million from the White Sox; Matt Guerrier, three years, $12 million from the Dodgers; Scott Downs, three years, $15 million from the Angels. Boston chose a two-year deal for an overweight Jenks who had lost his closer's job in Chicago and it's been a disaster.
DAISUKE MATSUZAKA -- 6 YEARS, $52 MILLION. Add the $51,111,111 posting fee to the contract and it adds up to a mistake that cost Boston more than $100 million. Constant battles over Dice-K's preparation and routine were either clashes of culture and tradition or simple belligerence. He was the antithesis of everything American fans are told is smart pitching: content to work slowly, nibble and hand out bases on balls rather than pitch to contact. He drove people nuts. His career in Boston is already over. Out for this season due to Tommy John surgery, his recovery course won't have him back until next September, when his contract ends. For their $100 million-plus investment, the Red Sox got a return of 49 wins, a 4.25 ERA and 1.40 WHIP and another free-agent mistake that's created a rotation hole this year.
CARL CRAWFORD -- 7 YEARS, $142 MILLION. We don't know if Jose Reyes will get "Carl Crawford money" this winter but we do know that last winter, Carl Crawford did. We certainly don't yet know if he'll be worth it. Crawford hit .155 in April. What's followed has been a mixed bag: .304 in May, .278 in June, .250 in July. After five seasons of at least 50 stolen bases in Tampa Bay, Crawford's speed game has yet to arrive in Boston. You get the feeling that when Crawford's confidence in his batting stroke settles in, the chaos he created on the bases will return. His key for this season is likely health; Crawford recently missed 24 games with a hamstring strain and then last week reportedly needed an injection for a left elbow strain.
The free-agent decisions creating questions about this season in Boston are hardly without precedent. Edgar Renteria was signed to a four-year, $40 million dollar contract prior to 2005 and spent one disastrous season on Fenway Park's infield committing 30 errors, more than his previous two seasons in St. Louis combined, and had to be dealt the following winter. Eventually, the Red Sox paid Julio Lugo $36 million to play the position. Lugo batted just .247 over his first two seasons in Boston while his defense was an erratic adventure. He was essentially given away to the Cardinals while Boston spent a season-and-a-half paying Lugo's contract. The Red Sox made the emotional decision to bring Mike Lowell back after their 2007 World Series win, with a three-year, $37.5 million contract that yielded an average of .274, 13 HR and 58 RBIs as Lowell gamely limped through his final three seasons, the last of which saw Lowell able to make only four starts at third base because of injuries.
Deep pockets and a well-stocked farm system make all of these free-agent mistakes affordable. This Boston front office has done a great deal right. As with Gonzalez, it traded promising prospects for Josh Beckett and then paid big money to keep him. It picked up David Ortiz after he'd been released by the Twins and again, paid to keep him. The Red Sox have developed their own franchise cornerstones like Dustin Pedroia, Youkilis, Ellsbury and Jon Lester, plus Buchholz, Bard and Papelbon. Defensive whiz Jose Iglesias could take over at shortstop next year. First, the Red Sox need to overcome the stream of free-agent mistakes still in play this season.
(Justin Havens of the Baseball Tonight research force contributed to this post. Follow Justin on Twitter @jayhaykid.)
Follow Steve Berthiaume at Twitter @SBerthiaumeESPN.