As a batter, Cabrera is a good fastball line-drive hitter that uses all fields with occasional power. He is a consistent basestealing threat, and he also has the aggressiveness to hustle out numerous doubles and triples.
Cabrera is regarded as a one of the best shortstops in the game. He has an excellent range to both sides, soft hands and a strong arm. He won the Gold Glove Award in 2001. In 2003, he finished second among the league shortstops in batting average (.297), slugging percentage (.415), RBI's (80), and in stolen base percentage (24-to-26). Beside this, he is one of four Montreal players to have ever played all 162 games in a season, and the first to do it twice. Also, his 17 home runs in that season were the most ever by a shortstop in the Expos history.
Cabrera was traded by Montreal to the Boston Red Sox in the summer of 2004, on the last day of the July trading deadline. Cabrera made Boston fans forget their anger over the Garciaparra four-team deal, batting .294 with six home runs and 31 RBI in 58 games. He also brought stability to the shortstop position, which delighted the Red Sox pitchers. The trade, which also netted first baseman Doug Mientkiewicz from the Twins, shored up Boston's infield defense and energized the team, which went 42-19 after the deal to win the American League's wild card (56-45 before the trade). "He is a game-changer in the field for me," Curt Schilling said.
Following his 2004 World Series victory with the Red Sox, Cabrera signed as a free agent with the Los Angeles Angels organization. Orlando replaced fan favorite David Eckstein at the shortstop position. While it took Angels fans a while to warm up to Cabrera, he eventually became a fan favorite himself after an excellent defensive season in 2005.
Cabrera is a career .267 hitter with 84 home runs and 500 RBI in 1151 games. As a shortstop, he has compiled 1769 putouts, 3204 assists, and 113 errors in 5086 total chances, for a .978 fielding percentage.
In his first game back to Fenway Park as an Anaheim Angel in June 2005, Cabrera was greeted with a standing ovation which lasted 30 seconds before he walked to the plate. Red Sox fans still give him standing ovations upon each plate appearance at Fenway Park.
Orlando Cabrera was traded to the Chicago White Sox prior to the 2008 MLB season.
Cabrera has been given several nicknames by teammates, fans and media.
- O-Dawg (commonly used by Rex Hudler)
- The Wizard of O.C. (bestowed on him by Angel broadcaster Steve Physioc)
- Signed as a non-drafted free agent by the Montreal Expos (June 1, 1993).
- Traded by the Montreal Expos to the Boston Red Sox as part of 4-team trade in which the Boston Red Sox sent Nomar Garciaparra and Matt Murton to the Chicago Cubs; the Chicago Cubs sent Brendan Harris, Alex Gonzalez, and Francis Beltran to the Montreal Expos; the Minnesota Twins sent Doug Mientkiewicz to the Boston Red Sox; and the Chicago Cubs sent Justin Jones to the Minnesota Twins (July 31, 2004).
- Granted free agency (November 1, 2004).
- Signed by Los Angeles Angels (January 12, 2005).
- Traded by the Los Angeles Angels to the Chicago White Sox in exchange for pitcher Jon Garland (November 21, 2007).
- Gold Glove (2001)
- Twice led league in games played (2001, 2003)
- Hit a home run on his first at-bat as a Red Sox, becoming the eighth Boston player to accomplish this feat (August 1, 2004)
- Won the World Series with the Boston Red Sox in 2004. It was the franchise's first World Series since 1918.
- Had a straight steal of home plate on July 2, 2006, the first such time it had happened by an Angels player since 1997.
- Had a 63-game on-base streak in early-through-mid 2006, which was among the top five streaks of all time. Ted Williams holds the major league record with 84 straight games reaching base by a hit, walk, or hit-by-pitch.