J.D. Drew celebrates after hitting a grand slam in Game 6 of the 2006 ALCS. (AP)

Red Sox outfielders J.D. Drew and Mike Cameron have struggled mightily to keep their heads (and batting averages) above water this season. Mostly due to that pair’s struggles, the Sox rank near the bottom of the majors in terms of right field production in most major categories.

For all of Drew’s struggles, Cameron fared even worse. Everything changed on Thursday when the Sox decided to release the 17-year veteran in the final season of a two-year, $15.5 million deal.

So, what does this mean for Drew? It’s time to start swimming.

In 64 games this year, Drew is having the worst year of his career. His batting average (.235), OBP (.333), slugging percentage (.327) and OPS (.660) all would be career lows; his four home runs and 18 RBIs likewise suggest his poor output. He has also dealt with a number of injuries that have limited him to 64 of the Sox’ first 81 games. Most recently, Drew suffered a left eye contusion and missed the first two games of last week’s series against the Phillies.

With his diminished output, Drew is, once again, a highly scrutinized player for the Sox, something that has been the case almost from the day that word that the Sox had signed the free agent to a five-year, $70 million contract emerged after the 2006 season.

Yet as much criticism as Drew has faced, his deal was far from the biggest given to an outfielder that offseason. Indeed, his was simply part of a wealth of long-term deals that were given out like candy to outfielders that winter. As the Sox take on the Astros for three days in Houston, it is a reminder that the Sox weren’t alone in taking a plunge into the deep end of the free-agent pool five winters ago.

Let’s fire up the flux capacitor and turn back time to the 2006-07 offseason — Jan. 26, 2007, to be more specific — when the Red Sox inked the then nine-year veteran to a five-year, $70 million deal. Drew was coming off a strong season in 2006 in which he appeared in a career-high 146 games, recorded his first 100 RBI season and batted a more-than-respectable .283 with a .393 OBP. With Trot Nixon‘s contract expiring and no suitable replacement available on roster (unless you count this guy), it’s easy to see why Drew — even with his fragile reputation — was an attractive free agent target, resulting in his deal that made him the highest-paid player on the team.

However, he wasn’t the only high-profile outfielder on the market. Indeed, he didn’t even receive the biggest deal of that winter. After all, in that same offseason of 2006-07, the Astros gave a six-year, $100 million deal to Carlos Lee. Like Drew, Lee — who hit .305 with a .354 OBP, .524 slugging mark and .878 OPS while averaging 29 homers and 107 RBI in the first three years of his deal — began fading in 2010 when, at age 34, he plunged to hitting .246/.291/.417/.708.

Unlike Drew, Lee has bounced back somewhat this year (.270/.321/.427/.748), but his defense — never considered elite — has dipped to the point where he is considered something of a DH with a glove. He splits his time between left field and first base, when interleague play doesn’t permit the Astros the luxury of using him as a designated hitter. So, from that standpoint, his defensive value — already limited — is in a state of decline. That situation could become more pronounced as Lee plays out not just this season but next under the terms of his six-year deal.

Aside from Drew and Lee, Gary Matthews Jr., Juan Pierre and Alfonso Soriano were all there for the taking that winter. The Blue Jays, based on the prevailing trends of that market, also made a bold move to extend Vernon Wells on a long-term deal that winter. Let’s take a few minutes to compare Drew’s production with that of these five players in the last half-decade.

Drew (BOS, 2007-11):

Totals: 589 G, .267 average, .373 OBP, .461 SLG, .834 OPS, 80 HR, 282 RBI

There may never be a consensus about Drew’s time in Boston. On the one hand, he’s been a well above-average on-base guy and, during his middle three years in Boston, he averaged 22 homers a year and had a .495 slugging percentage. Moreover, he’s been one of the best defensive right fielders in the game during his tenure with the Red Sox.

On the other hand, Drew has done most of his best work with the bases empty. Hitting behind such sluggers as David Ortiz, Manny Ramirez, and Kevin Youkilis, he has yet to drive in more than 68 runs in a season for Boston, he’s averaged a relatively modest 131 games per season due either to injuries or days off against lefties and his numbers have been taking a nosedive for about a year.

Drew’s most notable contribution to the franchise came on October 20, 2007 with Boston trying to stave off elimination in Game 6 of the ALCS. His first-inning grand slam off Indians starter Fausto Carmona took the life out of Cleveland, and is remembered by some as the $70-million swing. One or two plays can change a player’s legacy in a heartbeat (Kirk Gibson, Bill Buckner, etc.). And Drew had subsequent huge postseason hits for the Sox, including a game-winning ninth-inning homer in the 2008 ALDS and a walkoff hit against the Rays in the Sox’ memorable Game 5 comeback in the ALCS that year.

Now, his competition …

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Carlos Lee (HOU, 2007-11)

Totals: 673 G, .287 average, .336 OBP, .487 SLG, .823 OPS, 117 HR, 455 RBI

As expensive as Drew was, Lee cost more. “El Caballo”signed a six-year, $100 million deal with the Astros in the 2006 offseason — giving him an annual salary of roughly 19 percent more than Drew. He’s hit for more average and power than Drew while driving in more runs, but Drew has a vastly better OBP and a superior OPS.

However, like Drew, he’s shown decline in his age 34 and 35 seasons; unlike the Sox with Drew, the Astros are also on the hook for Lee’s age 36 season in 2012.

Defensively, he is a definite downgrade from Drew. Lee had the lowest range factor of all starting major league left fielders in 2009 and was moved to first base permanently last season.

Gary Matthews Jr. (LAA, NYM, 2007-10)

Totals: 406 G, .245 average, .322 OBP, .377 SLG, .699 OPS, 30 HR, 169 RBI

Matthews signed a five-year $50 million contract entering the 2007 season based almost solely on his breakout season the year before. In 2006, Matthews tallied 19 home runs, 44 doubles, 79 RBIs and 194 total hits. He was named to the All-Star team and even made his way onto the MVP ballot, finishing 30th.

But even without factoring in his reported use of HGH just months after signing the deal, the switch-hitting son of Phillies broadcaster Gary Matthews would leave the Angels with plenty to regret about his signing.

In the first year of the deal, Matthews hit .252 (61 points lower than the year before) with a .323 OBP (a 48-point drop) and struck out a career-high 102 times. It only got worse from there. That was his highest average during his three-year stint in Anaheim.

Signed to be a center fielder, he was pushed to the corners when the Angels signed Torii Hunter the following winter. Ultimately, his playing time dwindled to that of a backup, and in January of 2010, he was traded to the Mets. As part of the deal, the Angels still had to pay $21.5 million of the $23.5 million remaining in his contract.

Juan Pierre (LAD, CHW, 2007-11)

Totals: 663 G, .285 average, .337 OBP, .339 SLG, .676 OPS, 3 HR, 167 RBI, 213 SB, 67 CS

Excluding an injury-shortened 2008 season, Pierre (5 years, $44 million) has essentially lived up to his reputation. The three-time stolen base champion has made his impact on the basepaths, stealing an average of 43 bags in the first four seasons of the contract. Pierre has posted decent batting averages and middle-of-the-pack OBPs.

However, while he’s continued to be an impact baserunner, the value of his defense has gone down. Signed to be a center fielder, he had made the permanent move to left field by the second year of his contract. There, his utter lack of power (just three homers in five years) meant that his batter’s box production was well below-average for his position.

Traded to the White Sox in December of 2009, L.A. picked up $10.5 of the remaining $18.5 million on his contract. He had a strong 2010 season for the White Sox, but this year, at age 33, he’s swiped just 11 bases and been caught stealing 10 times, by far the worst ratio in his career (excluding his rookie year in Colorado). Also, he is hitting a career-low .262 through 78 games.

Alfonso Soriano (CHC, 2007-11)

Totals: 573G, .271 average, .325 OBP, .505 SLG, .830 OPS, 120 HR, 314 RBI, 53 SB

In his lone season with the Nationals in 2006, Soriano set a new career-high with 46 homers. He also stole 41 bases and drove in 95 runs. He drew a career-high 67 walks and batted a respectable .277. Those numbers drove the Cubs to offer the former Yankee second baseman the largest contract in franchise history: eight years, $136 million.

After a solid 2007 campaign in which Soriano just missed breaking the .300 line and hit 33 homers (albeit with a modest .337 OBP), he began to struggle. Playing just 109 and 117 games respectively in the next two seasons, his production dropped dramatically. In 2009, he finished with 20 home runs, 55 RBIs and a .251 batting average.

He’s bounced back over the last two years (at ages 34 and 35), hitting .260 with an .814 OPS and 38 homers since the start of 2010. Still, he’s been a below-average left-fielder for the life of the deal, and the Cubs remain on the hook for three more years (and $54 million) after this season concludes.

Vernon Wells (TOR, LAA,  2007-11)

Totals: 627 G, .263 average, .314 OBP, .443 SLG, .757 OPS, 92 HR, 338 RBI

Wells was one of the best all-around players in 2006, finishing with 32 home runs, 106 RBIs, and a .303 average. He also took home his third straight Gold Glove award. The Blue Jays rewarded their star with a seven-year, $126 million extension that was to begin in 2008.

Before that contract even began, there were signs that it could be a disaster. He hit half as many bombs in 2007 and batted a miserable .245. Though he showed signs of life the year after hitting .300 again, he was never remotely close to the same player he was before agreeing to the deal.

This past January, Wells was traded to the Angels for catcher Mike Napoli and outfielder Juan Rivera. The fact that the Jays were able to unload his contract was considered an enormous coup. Currently, he has a .216 average, 10 homers and 26 RBIs. He’s moved from center to left field with the Angels. His .617 OPS is among the worst in the game, and after this season, he will still have three more seasons at $21 million each coming his way.

Matt Goisman contributed to this report.