Rollins was named the National League (NL) Most Valuable Player (MVP) in 2007, as the Phillies won their division in the first of five consecutive seasons.

[4] His mother played competitive fastpitch softball, and he credits the experience with helping him develop a cerebral approach to the game, as well as a passion for the middle infield.

[7] His sister, Shay Rollins, was a starter on the University of San Francisco's women's basketball team,[8] and he is the cousin of former MLB player Tony Tarasco.

Rollins played the trumpet while growing up, and participated in various MC Hammer and Mavis Staples music videos during his adolescent years.

While playing alongside future Phillies teammates Pat Burrell, Johnny Estrada, Adam Eaton, and Brandon Duckworth, Rollins batted .244/.306/.354 with 18 doubles and 23 stolen bases; once again, he was the youngest player on the team.

Rollins spent the entire 2001 season with the major league Phillies and hit his first MLB home run on May 2 off of Brian Bohanon of the Colorado Rockies.

[9][30] Among his season highlights were a game-winning RBI against John Smoltz in June, and stealing his 100th career base in September, both of which occurred in games against the Atlanta Braves.

The workouts with Gwynn had helped, but it was joining morning sessions with (Bobby) Abreu that enabled him to sting the ball with authority and consistency.

[9] Under new manager Charlie Manuel, whose offensive strategy predominantly revolved around hitting many home runs, Rollins struggled to post a strong batting average early in the Phillies' 2005 season.

[35] Overall, Rollins compiled his fourth career quadruple-double, tying Johnny Damon for most among active players, and batted .290/.338/.431 with 12 home runs, 54 RBIs, and 41 stolen bases.

[1][9] The 2006 Phillies season began with much hype surrounding Rollins, and whether he could extend his hitting streak to pass Joe DiMaggio's record 56 games.

[40] Before spring training, Rollins announced that the Phillies were the "Team to Beat" in the National League East: The Mets had a chance to win the World Series last year.

[9] In August, the Mets' lead began to dissipate, as the Phillies combined several solid series; Rollins was a key component of their success.

[48] On the last day of the 2007 season, Rollins became the seventh player to collect at least 20 doubles, 20 triples, and 20 home runs in one season when he hit his 20th triple of the year in a 6–1 win over the Washington Nationals that clinched the National League East division championship for the Phillies, which confirmed Rollins' preseason assertion of the Phillies preeminence.

[30] After beginning the season by hitting a home run on opening day, Rollins landed on the disabled list (DL) for the first time in his career in early April, suffering an ankle sprain.

[9][30] At the conclusion of the season, Rollins was honored with a Fielding Bible Award for defensive excellence as the top MLB shortstop during the year.

During the season, he joined Craig Biggio, Barry Larkin, and Paul Molitor as the only players in MLB history to record 2000 hits, 350 stolen bases, and 150 home runs as a member of one team.

[9] Despite the achievements, overall, the season was a decline from previous years; his isolated power (ISO) was among the worst in the major leagues, he attempted to steal the fewest bases in his career, and his defense "tanked" according to fielding metrics.

[9] Rollins attracted media attention in the offseason prior to 2014 when he supposedly expressed disinclination or lack of motivation after commenting "who cares" in regards to spring training; Buster Olney penned a column suggesting that there was a sentiment within the Phillies' organization that he should be traded (the rumors were dispelled by Rollins and Phillies general manager Rubén Amaro, Jr. as ridiculous).

[76][77] Following the season, Rollins and recently retired Chicago White Sox captain Paul Konerko became the first ever co-winners of the Roberto Clemente Award.

[78] On December 19, 2014, Rollins was traded to the Los Angeles Dodgers in exchange for minor league pitchers Tom Windle and Zach Eflin.

[81] He struggled offensively with the Dodgers, hitting a career low .224 (the lowest batting average among all qualified major league batters)/.285/.358 with 13 homers and 41 RBI.

[88] On December 19, 2016, Rollins signed a minor league contract with the San Francisco Giants that included an invitation to spring training.

[90] In 2019, Rollins returned to the Phillies in two separate capacities: in January, as a special advisor for the team;[91] and in March, as an on-air commentator for their television broadcasts.

[24] This contributed to his propensity to swing early in the count, and chase high pitches, seeking to hit home runs rather than get on base, the stereotypical role of a leadoff hitter.

[22][24] To help alleviate those predominantly negative tendencies, he worked with Tony Gwynn prior to the 2003 season on using the whole field, and hitting more ground balls than pop-ups.

[25] Overall, he "always had a hard time accepting that he is vertically challenged at 5-foot-8", which contributed to his inclination to strive to hit for power rather than contact, and to seek to pull the ball rather than use the whole field.

[99] Rollins attributes some of his defensive prowess to experience, noting that he played in MLB for a long enough time to know most hitters' tendencies and to learn how to read swings, both of which helped him appropriately position himself to get to as many balls as possible.

[99] In their 2011 season preview, Lindy's Sports commented that Rollins was an upper-echelon shortstop "with soft hands, excellent agility and plus range left and right" and praised his strong throwing arm, especially from the hole.

[107] An active philanthropist, Rollins and his wife Johari have participated in several charitable endeavors including the creation of The Johari & Jimmy Rollins Center for Animal Rehabilitation, which is located in Woolwich Township, New Jersey, and provides several medical rehabilitation services for animals[108] and an annual BaseBOWL charity bowling tournament to benefit the Arthritis Foundation.