Cabrera is the younger brother of Jolbert, a former major league outfielder who currently plays with the Fukuoka SoftBank Hawks of Japan's Pacific League.

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), runs batted in (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 Angel fans a while to warm up to Cabrera, he eventually became a fan favorite himself after an excellent defensive season in 2005.