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[[File:J. D. Drew.jpg|175px|thumb|Drew celebrating a Red Sox 2008 playoff victory]]
On October 20, 2007, Drew hit a [[Grand slam (baseball)|grand slam]] in Game 6 of the [[2007 American League Championship Series|2007 ALCS]] with the Red Sox facing elimination.<ref name=":1">{{Cite web|date=September 9, 2008|title=Red Sox's Drew
In 2008, Drew hit one of the longest home runs in Fenway Park history. According to the ESPN Home Run Tracker, it was measured at 460 feet. He finished with a .280 average, with an [[On-base percentage|OBP]] of .408 and a [[slugging percentage]] of .519.<ref name=":0" /> At the end of June, Drew was named the AL Player of the Month after hitting .337 and hitting 12 home runs while taking over for [[David Ortiz]]'s three-spot in the lineup while he was on the disabled list.<ref>{{cite news|last1=Silva|first1=Steve|date=July 2, 2008|title=Drew named AL player of month for June|work=[[The Boston Globe]]|url=http://www.boston.com/sports/baseball/redsox/extras/extra_bases/2008/07/drew_named_al_p.html|access-date=July 2, 2008}}</ref> Drew was officially announced as an AL [[MLB All-Star|All-Star]] reserve on July 6. This was Drew's first All-Star game appearance. He hit a two-run homer in his first at-bat as an All-Star en route to winning the [[Major League Baseball All-Star Game MVP Award|game's MVP award]]. In what was to become the longest All-Star Game time-wise in MLB history, the American League (and Drew's Red Sox) manager [[Terry Francona]], having almost run out of pitchers, contemplated putting Drew, a former high school hurler, on the mound to close the game. "I'd have been ready," Drew said. "I've had an opportunity to throw a lot in the outfield. I don't know if I would have gotten anyone out, but I'd have thrown something up there."<ref>{{cite web|last=Edes|first=Gordon|date=July 16, 2008|title=The longest goodbye|url=http://www.boston.com/sports/baseball/redsox/articles/2008/07/16/the_longest_goodbye/|access-date=December 21, 2012|work=[[The Boston Globe]]}}</ref> Drew later visited the 15-day disabled list, spending from August 27 to September 8 on the DL with a strained lower back.<ref>{{Cite web|date=August 26, 2008|title=
On October 3, in Game 2 of the [[2008 American League Division Series]] against the [[Los Angeles Angels of Anaheim]], Drew hit a go-ahead two-run home run.<ref>{{Cite web|last=Browne|first=Ian|date=October 4, 2008|title=Drew delivers back-breaking blow|url=http://mlb.mlb.com/news/gameday_recap.jsp?ymd=20081003&content_id=3586948&vkey=recap&fext=.jsp&c_id=bos|url-status=live|archive-url=https://web.archive.org/web/20081006005437/http://mlb.mlb.com/news/gameday_recap.jsp?ymd=20081003&content_id=3586948&vkey=recap&fext=.jsp&c_id=bos|archive-date=October 6, 2008|access-date=May 30, 2021|website=[[Boston Red Sox]]}}</ref> On October 16, in Game 5 of the [[2008 ALCS|American League Championship Series]] against the [[Tampa Bay Rays]], Drew helped to bring the Red Sox back from a late-inning seven-run deficit with a two-run home run in the eighth inning and then delivered the walk-off hit in the ninth. The Game 5 comeback, sparked by Drew, is the second-biggest in postseason history and is the largest for a team on the brink of elimination.<ref>{{Cite web|date=October 17, 2008|title=Drew's game-winning single keeps Red Sox alive in ALCS|url=https://www.espn.com/mlb/recap/_/gameId/281016102|archive-url=https://web.archive.org/web/20210602213405/https://www.espn.com/mlb/recap/_/gameId/281016102|url-status=dead|archive-date=June 2, 2021|access-date=May 30, 2021|website=[[ESPN]]|language=en
After the 2009 season, Drew's statistics began to decline. That year, he hit .279 with an .392 [[On-base percentage|OBP]] while hitting 24 home runs and 68 RBI. The following year, he hit .255 with 22 home runs with 68 RBI. However, he played in 139 games, his highest total since 2007 when he joined Boston. In 2011, Drew hit .222 with four home runs and 22 RBI. He played in 81 games and had a .315 OBP. Drew retired from professional baseball at the end of the 2011 season.<ref>{{Cite web|last=Leitch|first=Will|date=April 18, 2020|title=Better than you remember: J.D. Drew|url=https://www.mlb.com/news/looking-back-at-career-of-j-d-drew|access-date=May 30, 2021|website=[[MLB.com]]|language=en}}</ref>
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