It was Dec. 16, 2009, and though Fenway Park was in the process of being converted to an icebox to host the Bruins, baseball had reasserted itself in Boston for a day. The Red Sox were unveiling a pair of shiny new baubles in their new home park.

True, the Red Sox acknowledged, they enter the deep end of the free-agent pool only reluctantly. But there are exceptions who justify faith in the open market, and, the Sox said, Mike Cameron (introduced at a morning press conference) and John Lackey (who commanded the floor in the afternoon) were two such exceptions.

Cameron, though 36 going on 37, represented an athletic freak who had defied the effects of age. The Sox signed him to a two-year, $15.5 million deal with the expectation that they were getting a terrific defensive outfielder who also clubbed about two dozen homers ever year.

And then there was Lackey, whom the Sox had signed to a five-year, $82.5 million deal – the most expensive free agent whom the Sox had landed during GM Theo Epstein’s years at the helm of Boston’s baseball operations.

Epstein was candid. The Sox always prefer to minimize the risk of free agent pitching, he said, by limiting the number of years of a deal, but the market reality dictated that it would take a five-year offer to land a player whom the Sox viewed as one of the best and most consistent right-handers in the game. And so it was that the team decided that Lackey was worth the plunge, the difference-maker who would justify the Sox’ investment.

One day, two exceptions, $98 million.

Last week, when the Sox designated Cameron for assignment, Epstein suggested that he’d made a mistake in signing the outfielder. Cameron was never the same player that the club had scouted once he suffered major abdominal injuries in spring training in 2010, resulting in the decision to cut bait at a time when the Sox were still on the hook for approximately $3.75 million.

The team isn’t in such a position with Lackey, but certainly it is in an anxious spot with the 32-year-old. Lackey was shelled on Monday, allowing seven runs on nine hits in 2 1/3 innings, as the Sox suffered a 9-7 defeat. (Recap.)

Often somewhat defiant after his losses, Lackey instead appeared at a loss after a game when he got hit around even though he felt like his arm strength and velocity should have allowed him to proceed. He said that it was “pretty obvious” that this has been the most puzzling stretch of his career, and was left to express hope rather than certainty that his lot – a 5-8 record and 7.47 ERA – will improve.

“Just continue to work hard. I’ve made a lot of adjustments kind of on the fly,” said Lackey. “Hopefully some of those will start to turn into results here soon.”

With roughly 3½ seasons and about $53 million remaining on his deal, it is premature to declare the right-hander a bust. The possibility certainly exists that he could regain the form that made him an All-Star with the Angels and convinced the Sox to sign him in the first place.

Still, it would be naïve to assume that such an outcome will occur. First, at 32, Lackey is at an age where pitchers are typically in a state of decline, the accumulated wear and tear of years on the mound becoming increasingly apparent.

Indeed, the Sox expected that they were signing the pitcher through seasons of decline (especially at the back end of the five-year deal); they simply expected and hoped that the process would be gradual. With his record now 19-19, and his ERA an unsightly 5.17 with the Sox, the alarm bells are ringing.

Then again, as much pomp and circumstance as there is to greet any big money free agent signing, it can no longer be viewed as a surprise when such deals end with a splat. Certainly, the Sox’ free-agent history under Epstein would suggest as much.

The Sox have had instances of remarkable free-agent successes. The $1.25 million that the team dropped to add David Ortiz in 2003 might be the most significant investment in franchise history. Hideki Okajima became an All-Star after signing a two-year, $2.5 million deal. Adrian Beltre likewise offered the Sox an incredible return on the one-year, $9 million deal he signed for the 2010 year.

But the pricier investments have offered suspect returns. Under Epstein, the team has given 12 players free agent deals that included guarantees of at least $10 million. The returns have been suspect at best. A brief synopsis:

2003-04: Closer Keith Foulke (3 years, $21 million)
He was likely the second most important contributor (behind Ortiz) to the Sox’ championship run in the 2004 playoffs, so it would be difficult to quibble. Still, injuries and diminished effectiveness made him a virtual non-factor for the last two years of the deal – though he did net the Sox a draft pick on his way out the door.

2004-05: Shortstop Edgar Renteria (4 years, $40 million)
Renteria came with a reputation as a Gold Glove defender, but instead made more errors than anyone in baseball in 2005, and his offensive production was menial. After one year, the Sox paid the Braves $8 million to take him off their hands in a deal that netted the team Andy Marte, a player who was subsequently moved as the key prospect in a deal for Coco Crisp.

2004-05: Starter Matt Clement (3 years, $25.5 million)
He pitched well for a half a season, earning a place on the AL All-Star team, and then saw his career spiral quickly downwards. He performed poorly in the second half of 2005 and first half of 2006. Near the end of the year, surgery revealed significant labrum and rotator cuff damage, and Clement never again pitched in the majors.

2004-05: Catcher Jason Varitek (4 years, $40 million)
The Sox re-signed Varitek after the World Series run, and for the first three years of his deal, he remained a well above-average offensive and defensive catcher. Though he remained the backbone of the Sox clubhouse, his production took a hit in the last year of the four-year deal. Still, in retrospect, the Sox have no reason to regret this deal.

2006-07: Shortstop Julio Lugo (4 years, $36 million)
Lugo played well down the stretch and at times in the 2007 postseason, so he wasn’t a total and complete washout. But he was close. He hit .251 with a .664 OPS (more than 100 points below the .770 OPS he had in Tampa Bay) in two and a half years with the Sox, and his defense was atrocious. The Sox dumped him at the All-Star break in 2009, at a time when he was still owed more than $13 million.

2006-07: Right fielder J.D. Drew (5 years, $70 million)
Drew may be nearing the end (the jury remains out on that one), but he has delivered far more return on the investment than most would believe. Entering Monday, he had a .266 average, .373 OBP, .461 slugging mark and .833 OPS for the Sox, with his right field defense, on-base skills and power numbers all qualifying as above average. He may not have been the player whom people expected to see for $14 million a year, but he was also far from a bust.

2007-08: Third baseman Mike Lowell (3 years, $37.5 million)
The Sox reluctantly extended their offer to the reigning World Series MVP to three years, and Lowell was so enamored of his time in Boston that he walked away from a four-year offer from the Phillies at a similar salary. However, a degenerative hip condition left him immobile by the end of the 2008 campaign, and his production over his final two years in Boston was limited by the injury.

2009-10: Shortstop Marco Scutaro (2 years, $12.5 million)
Scutaro has been, essentially, the same offensive player with the Sox that he had been throughout his career prior to signing his free agent deal. Entering Monday, he’d hit .274 with a .332 OBP, .384 slugging mark and .716 OPS in Boston. His pre-Sox career numbers were .265/.337/.384/.721.

2009-10: Starter John Lackey (5 years, $82.5 million)
Lackey has just four quality starts in 13 outings in 2011, and it would be impossible for the Sox not to be concerned about what he will be able to deliver both over the duration of this season and between now and the end of his deal in 2014.

2009-10: Outfielder Mike Cameron (2 years, $15.5 million)
In two years, health and production limited Cameron to just 81 games. He hit .219 with a .285 OBP, .352 slugging mark and .637 OPS, and his defense was he was never the impact defender whom the Sox believed they were signing.

2010-11: Outfielder Carl Crawford (7 years, $142 million)
Crawford has had an inglorious start to his Sox career, hitting .243 with a .275 OBP, .384 slugging mark and .659 OPS before landing on the DL with a hamstring injury suffered in mid-June. Still, after what he acknowledged to be a period of adjustment, he was showing signs of being able to impact the game with his bat, legs and glove. It will be some time before the measure of this deal can be taken.

2010-11: Reliever Bobby Jenks (2 years, $12 million)
Jenks is about a quarter of the way through his deal. Because of a pair of DL stints, he has appeared in just 18 games, so it remains to be seen just what the Sox have in the right-hander. Still, he shows impressive raw stuff, even if his results to date have been poor. He has a 6.75 ERA, putting him in position to suffer a rise in ERA for the third straight year.

In sum, the Sox have walked away from three of their 12 eight-figure free agent contracts (Renteria, Lugo, Cameron) at considerable expense. They have seen injuries devastate the performance of three of the players whom they signed (Foulke, Clement, Lowell). The jury remains out on three players (Crawford, Jenks, Lackey), even though the initial returns on all three have been below career norms. And three players have delivered at least reasonable approximations of what they were signed to do (Varitek, Drew, Scutaro).

This pattern comes as little surprise to the Sox. The team has long stated explicitly its reservations about free agency. This season, Epstein took stock of the high cost -- and high risk -- involved in bidding for a player on an open market when the team signed Clay Buchholz to a four-year extension for just under $30 million that could keep the right-hander away from free agency through his age 32 season.

"Free-agent pitching is a tough way to go. We’ve dipped into those waters. If you can build an organization and not have to go into the free-agent pitching market, that’s a good thing," said Epstein. "It’s inevitable. You’ll have to go into it from time to time. But if you can develop homegrown pitching, control it, maybe control a couple years of free agency a little bit, that’s a very valuable thing.

"We all know the cost of free agent pitching," he added. "The longer we can put off that decision, from the club’s perspective, the better. While [Buchholz's deal is] a lot of money, compared to what it costs to bring in a free-agent contract on a long-term contract, it’s actually not that much money."

Lackey, of course, was part of the subtext. In Buchholz, the Sox signed a pitcher whom they know, who has proven his ability to succeed in Boston, who is young and should be entering his prime, at a fraction of the cost of a pitcher like Lackey. In an ideal world, the team would be thrilled to have a rotation filled with entirely homegrown pitchers who are young, talented and affordable. But that is not realistic, resulting in occasional -- and risky -- forays into free agency.

The Sox are not alone in finding those waters to be perilous. Many teams have received first-hand evidence to suggest that the open market often rewards past performance at a time when a player’s age results in the erosion of his skills.

More often than not, the question with free agent contracts is not whether there will be wasted money, but how much. Certainly, that has been largely true of the Sox’ dip into such waters.