Rolando attended Fort Hamilton high school where his team won the New York City PSAL City championship in 1989. After high school, Rolando continued to pursue his dreams of playing baseball by attending tryouts for the New York Mets, Cincinnati Reds, and Montreal Expos. At the age of 21, Rolando became a New York City Police officer where he continued to play baseball at the semi-pro level with the police department baseball team. The New York Police department team traveled throughout the United States, Dominican Republic and Puerto Rico playing high-level baseball against Single-A and Double-A professional teams for charity as well as other big city police departments.
After World Trade Center attacks, Rolando transitioned from playing baseball to coaching baseball and basketball in the Police Athletic league, AAU, and Federation baseball. Rolando has coached several players who have gone on to play Division 1 basketball, One baseball player who played 12 seasons in the Major leagues, and One player who converted to football in college and now plays with the Seattle Seahawks.
Since relocating to Texas in 2013 Rolando has been involved coaching baseball and softball in the Plano Baseball Association, Denton Boys Baseball, and Little Elm Little recreational leagues. Rolando has also coached Select AAA-Majors teams with DFW Express. Rolando coaches all aspects of baseball and softball and team practices.