1997: Drafted by the Philadelphia Phillies The
Philadelphia Phillies made Drew the second overall pick, after pitcher
Matt Anderson, in the
1997 MLB draft. Drew and his agent
Scott Boras chose not to sign with the Phillies, insisting Drew would not sign for less than $10 million. The Phillies had no plan to pay an unproven player this amount of money, and despite Boras' warnings, drafted Drew nonetheless. They offered him $2.6 million. Consequently, Drew ended up playing for the
St. Paul Saints of the independent
Northern League. Boras had Drew sign with an
independent baseball league because of a
loophole in the rules of the
MLB draft.
1998–2003: St. Louis Cardinals After playing for St. Paul in the 1997 season, Drew was selected in the first round of the
1998 MLB draft, fifth overall, by the
St. Louis Cardinals. In June he signed a $7 million contract, On August 10, 1999, in Drew's first game at
Veterans Stadium in Philadelphia, he was booed loudly, and even had batteries thrown at him by two fans. The
Phillie Phanatic got into the act, dropping two large trash bags marked with dollar signs in the outfield between innings. Drew struggled to stay healthy, landing on the
disabled list every season he played in St. Louis. In his book
Three Nights in August,
Buzz Bissinger mentions former manager
Tony La Russa's frustration with Drew's lack of passion. La Russa tells Bissinger that it seemed Drew had decided to "settle for 75%" of his talent, in large part because of his enormous contract.
2004: Atlanta Braves On December 13, 2003, Drew was traded to the
Atlanta Braves along with
catcher Eli Marrero for starting pitcher
Jason Marquis,
relief pitcher Ray King, and rookie prospect
Adam Wainwright. There, he had the best season of his career while finally managing to stay healthy. In , he displayed excellent power, patience, and defense, hitting .305 with 31 home runs, 118
walks, and 93 RBI, finishing sixth in the MVP voting.
2005–2006: Los Angeles Dodgers In December 2004, Drew signed a five-year, $55 million contract with the
Los Angeles Dodgers, which included an escape clause after the second year. Roughly halfway through the 2005 season, Drew's season was again cut short after being hit on the wrist by a pitch from
Arizona Diamondbacks' pitcher
Brad Halsey. On September 18, 2006, Drew was part of only the (then) fourth-ever set of back-to-back-to-back-to-back home runs with fellow Dodgers
Jeff Kent,
Russell Martin, and
Marlon Anderson. In 2006, Drew exercised his contract opt-out clause, forgoing $33 million over the next three years to become a
free agent. Dodgers general manager
Ned Colletti said in a teleconference that he was "surprised how it came down. Everything we had heard, everything that had been written led us to believe the player loved being here." This was especially a surprise because a few days before, Drew had told an
LA Times columnist on how happy he was in LA and that he was looking forward to the upcoming 2007 season. Drew had a very good season, batting .284 with 20 home runs and 100 RBI.
2007–2011: Boston Red Sox On January 26, , Drew officially signed a five-year contract with the Red Sox worth $70 million. Drew's revised contract had a clause that allowed the Red Sox to opt out of Drew's five-year contract after three or four years if Drew has extensive injuries due to a previously existing problem in his right shoulder. Drew was again part of a set of four consecutive home runs on April 22, 2007, in a game against the
New York Yankees, this time joining with
Manny Ramírez,
Mike Lowell, and
Jason Varitek. He is the only player to participate twice in a string of four straight home runs, and he was the second player to go deep in each instance. Drew finished the 2007 season with a .270 batting average, 11 home runs, and 64 RBI. On October 20, 2007, Drew hit a
grand slam in Game 6 of the
2007 ALCS with the Red Sox facing elimination. The home run, along with brother
Stephen Drew's for the
Arizona Diamondbacks, marks the third time that two brothers have both hit home runs in the same postseason. 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
OBP of .408 and a
slugging percentage of .519. Drew was officially announced as an AL
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
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." Drew later visited the 15-day disabled list, spending from August 27 to September 8 on the DL with a strained lower back. On October 16, in Game 5 of the
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. However, the Red Sox lost to the Rays in the seventh game. After the 2009 season, Drew's statistics began to decline. That year, he hit .279 with an .392
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. ==Personal life==