J.D. Drew came to the Red Sox as part of an ambitious offseason makeover that was expected to help a team that missed the playoffs renew its pursuit of World Series.

The hype of the Red Sox’ offseason of 2006-07 was every bit as intense as that surrounding the club’s moves this winter. Drew was the third part of a bold, wallet-opening winter, an outfielder who received a five-year, $70 million deal – at the time, the most money the Sox had ever committed to a single player under the current ownership group – following similarly aggressive moves to acquire Daisuke Matsuzaka (six-year, $52 million deal and $51.11 million posting fee) and shortstop Julio Lugo (four-year, $36 million contract).

In a way, the trio delivered. The Sox won the World Series in 2007, and all three played significant roles at times in that postseason. Even so, the overall return on the investments proved limited over the lives of their contracts.

Lugo was summarily dumped with a year and a half left on his contract, having become enough of a liability that the Sox were willing to swallow the final third of his contract. Matsuzaka was an important contributor in 2007 and 2008, but in three subsequent years has dealt with injuries and ineffectiveness, culminating in the decision to undergo Tommy John surgery that will render him unable to pitch for most of the remainder of his deal.

And then there is Drew, who delivered a walkoff single on Saturday to give the Sox a 9-8 win in 14 innings. (Recap.)

For all the criticism – some warranted, some not – of his game, he had mostly produced in his first four years with the Red Sox. He has been a superb defensive right fielder, covering tremendous ground in Fenway’s most challenging piece of real estate. His .377 OBP from 2007-10 ranked ninth among big league outfielders (min. 1500 plate appearances), ahead of peers like Josh Hamilton, Ichiro, Ryan Braun and Andre Ethier.

His .853 OPS ranked 12th among outfielders, just behind Ethier (.856), and ahead of others such as Carlos Lee (.833) and Alfonso Soriano (.832) who received far bigger contracts in that 2006-07 offseason.

Though Saturday offered Drew’s first regular season walkoff hit with the Red Sox, he has produced some huge moments in his Boston career: The grand slam in Game 6 of the 2007 ALCS, a go-ahead ninth-inning homer in Game 2 of the 2008 ALDS, a three-run homer and walkoff hit in Game 5 of the 2008 ALCS against the Rays, among others.

Drew’s contract and personality have always been lightning rods, yet for the most part, he has been a valuable contributor to the Sox. As free-agent signings go, Drew has come largely as advertised, the proverbial on-base machine with pop and a solid glove who has impacted the game in many ways for the Sox. Certainly, when evaluated against Matsuzaka and Lugo, the return on investment with Drew has been far greater.

Or, at least that had been the case entering the 2010 season. However, the final stages of Drew’s contract have seen the outfielder take something of a nosedive.

He was hitting relatively well through the first half of last year, carrying a .286 average with a .373 OBP, .504 slugging mark and .877 OPS into the Fourth of July. He was a legitimate middle-of-the-order presence for the Sox.

But things unraveled at that point. He went 0-for-3 with three strikeouts against Orioles lefty Brian Matusz, and from that point forward, he became an offensive liability, a status that continued into this year.

From last July 4 through Friday, among the 169 big leaguers with at least 400 plate appearances, Drew ranked 159th in average (.225), 126th in OBP (.319) and 133rd in slugging (.376).

His lack of productivity had been particularly pronounced of late, at a time when he’s missed some games due to some hamstring issues, while also simply sitting in favor of outfielders Mike Cameron (when the Sox faced left-handers) and Josh Reddick (in games when manager Terry Francona suggested he would like the young outfielder to offer “energy” to the lineup).

In the eight games preceding yesterday’s marathon, Drew was 3-for-25 (.120). He hadn’t walked once; he hadn’t driven in a single run; he hadn’t collected a single extra-base hit.

“J.D. has kind of a track record of grabbing on to that one month and kind of almost putting us on his back. You always wait for that, and he hasn't gotten to that point yet,” manager Terry Francona acknowledged last week. “He's taken good swings for sure at times, but he hasn't strung them together like he's capable of.

“I think we talk about that with everybody, but he seems probably a lot lately to take that cutter, slider away, kind of rolling over to second or first probably more than we're used to,” he added. “And he's trying. He's trying to stay back and drive it. He's just getting out ahead of it. His bat head's coming with it, his hands, and getting that weak ground ball or that popup.”

For most of the year, he’s been a non-presence in the lineup. He entered Saturday with 12 runs and 10 RBI – stats that are dependent on the production of those around him in the lineup, of course, but also symbols of the fact that he simply hadn’t been a part of meaningful offensive productivity.

Even on Saturday, when he delivered his game-winning hit, Drew spent more time as a rally killer than an instigator. He’d collected a run-scoring single in the early going, then struck out in four straight at-bats (the first time he’s ever whiffed four times with the Sox) before delivering his game-winning single. His struggles were sufficiently pronounced that, with Carl Crawford on second and two outs in the 14th, the A’s elected to have right-hander Guillermo Moscoso intentionally walk switch-hitter Jed Lowrie.

Considering that Lowrie had gone 0-for-6 with two punchouts, and that he was hitting .224 with a .597 OPS against right-handed pitchers for the year, the move was a startling commentary on the A’s lack of concern about Drew.

Drew made Oakland pay for delivering that indignity, taking a 90 mph fastball down the middle and lining it to right-center for a game-winning hit. The knock was satisfying both in giving the Sox a win and offering Drew what he hopes will be a building block for his difficult year to date.

“When I hit it, I knew there was no doubt. It’s a great deal, especially after having an afternoon like that. I had a couple of good at-bats early. Struck out four times in between other hit,” said Drew. “It was something to build on.”

“I’ve been searching a little bit out there,” he added after a 2-for-7 day that saw him notch his seventh multi-hit game and fourth multi-RBI game of the year. “That’s one of the key things today, I felt like I had some key swings, a couple of hits, a couple of RBIs. Ultimately winning the game works out good.”

Perhaps the day will represent a starting point for Drew to have a strong finishing leg in his Boston career. Perhaps not, and he will continue to see Cameron and Reddick – and, perhaps down the road, rehabbing outfielder Ryan Kalish – carve into his playing time.

For that matter, Drew’s struggles have led some talent evaluators outside the organization to wonder whether the Sox might make a play for an outfielder prior to the July 31 trade deadline, depending on what other needs the team faces at that stage of the season.

But for now, the Sox will hope that Drew can be what he has always been for them, at least for most of his first four years with them – an oft-scrutinized player who is largely impervious to the criticism of his game, someone who takes his walks, shows some power, plays terrific defense and serves as a quietly steady contributor. If Saturday represented a starting point in Drew being that player once again in 2011, then that would be a far more significant development than even a walkoff victory.