Nicknamed "J-Roll," Rollins comes from an athletic family, as his brother, Antwon, formerly played with minor league affiliates of the Texas Rangers and the Montreal Expos. His sister, Shay Rollins,was a starter on the University of San Francisco's women's basketball team, and Rollins is the cousin of former MLB player Tony Tarasco. Rollins also attended the same high school (Encinal High School) as former MLB pitcher Dontrelle Willis.

Though Rollins has developed into a five-tool player during his career due to significant increases in his power hitting, he is perhaps best known for his baserunning skills. He stole at least 20 bases every season from 2001 to 2009, with a career high of 47 in 2008. In this respect, Rollins emulates his childhood baseball hero, Rickey Henderson. Rollins is one of the most popular Phliadelphia Phillies players of all-time.