He played for the Atlanta Braves (1998–2004), Texas Rangers (2005–2006), Chicago Cubs (2007–2008), Cleveland Indians (2009), St. Louis Cardinals (2009), San Francisco Giants (2010–2011), Washington Nationals (2012), and Toronto Blue Jays (2013).

A Carlstadt, New Jersey, native, DeRosa attended the University of Pennsylvania, where he led the football team to consecutive Ivy League championships as their quarterback in 1994 and 1995.

[7] He attended Bergen Catholic High School in Oradell, New Jersey, where he earned all-state honors in baseball and in football.

[13][14] He made his MLB debut on September 2, pinch-hitting for Greg Maddux and striking out against Randy Johnson in a 4–1 loss to the Houston Astros.

[13] From June 9 through July 1, he served as a pinch hitter for Atlanta, going hitless in eight at bats while Walt Weiss was on the disabled list (DL).

[28] On July 21, he hit his first major league home run, a 10th-inning walkoff one against Graeme Lloyd that gave the Braves a 2–1 victory over the Montreal Expos.

Wanting a better defender with more experience, the Braves acquired Rey Sánchez to be their starting shortstop at the July 31 trade deadline.

[1] DeRosa was part of a playoff roster for the first time as the Braves won the National League (NL) East division.

[36] His pinch-hit RBI single against Aaron Fultz in Game 5 provided the only Atlanta run in a 3–1 defeat that eliminated the Braves from the playoffs.

[37] Healthy all year in 2003, DeRosa again played a number of positions: every infield spot, as well as left field and designated hitter.

[41] Starting at second base in Game 2 of the NLDS in place of Marcus Giles, who was recovering from a left leg bruise, DeRosa had an eighth-inning, two-RBI double against Dave Veres, driving in the go-ahead runs in a 5–3 victory over the Chicago Cubs.

[32] When Vinny Castilla signed with the Colorado Rockies after the 2003 season, the Braves decided to make DeRosa the starting third baseman in 2004, despite him batting just .231 with no extra-base hits in spring training.

[43] On June 15, DeRosa lost his starting job, as Chipper Jones moved from left field to third base, his position from 1995 through 2001.

Making it through the spring, he had his contract purchased before the start of the season, as the Rangers wanted an experienced utility infielder on their roster.

[59] Once Kinsler became healthy, DeRosa returned to being a utility player, but he remained a regular in Texas's lineup, even though his position changed frequently.

[1][63] Though the Rangers had been interested in retaining him, Chicago offered DeRosa the chance to start regularly at second base, an option that he preferred.

[67] On February 28, he had a successful catheter ablation at Northwestern Memorial Hospital to correct an irregular heartbeat, a problem which had plagued him since high school.

[68][69] On June 30, he hit a two-run home run against Barry Zito and a grand slam against Billy Sadler as the Cubs defeated the Giants 9–2.

[32][69] On December 31, 2008, DeRosa was traded to the Cleveland Indians for minor league pitchers Jeff Stevens, Chris Archer, and John Gaub.

[51] On August 4, he was hit by a pitch with the bases loaded in the 10th inning of a game against the Mets, forcing in the winning run in a 12–7 victory over New York.

[82] He had two hits in Game 2 and scored a run that put the Cardinals ahead in seventh, but they ultimately lost 3–2 following an error by Matt Holliday.

[81] DeRosa, who became a free agent at the end of the year, used the offseason to undergo surgery that sought to repair a torn tendon sheath in his left wrist.

Experiencing numbness in the fingers of his left hand, he underwent a medical examination on May 11 and found that the wrist surgery in 2009 had been a "failure".

[51][86][87] On July 1, he underwent season-ending surgery, a procedure that again sought to repair his tendon sheath, as well as releasing pressure on his carpal tunnel.

[88] Though DeRosa suffered from mild tendinitis in his left wrist during spring training, he began the 2011 season on the Giants' roster, though just as a reserve player.

[51] Despite DeRosa's limited playing time, he became an important mentor for his Nationals teammates, many of whom were much younger, including former first overall draft picks Bryce Harper and Stephen Strasburg.

[97][98] However, he travelled with the team during the postseason, even reading his teammates the "Man in the Arena" portion of a Theodore Roosevelt speech to inspire them before Game 4 of the NLDS.

[1] On January 22, 2013, DeRosa signed a one-year deal worth $775,000 with the Toronto Blue Jays, with a $750,000 club option for the 2014 season.

[99] Against the Astros on July 27, DeRosa hit his 100th career home run, a solo shot to lead off the second inning against Dallas Keuchel in an 8–6 loss.

Their daughter, Gabriella Faith, was born prematurely by two and a half months on July 28, 2003, after Heidi had spent 10 weeks in the hospital.