Born: JNovember 13, 1934
Died: August 30, 2017
Town: Hillsborough Township
Roland Vincent Massimino was born November 13, 1934 in Hillside. Rollie fell in love with basketball as a boy and was a guard on the Hillside High basketball team. Though not particularly tall or fast, he had a deep understanding of the game as a teenager. He continued playing while attending the University of Vermont in the mid-1950s, earning three varsity letters under coach Fuzzy Evans. The Catamounts went 25–44 while Rollie was on the squad. He went on to earn a masters at Rutgers in Health and Physical Education, and also snared his first coaching job, at Cranford High School. In 1959, Rollie returned to Hillside High as coach of the varsity basketball team and led them to a state finals in 1960–61 and again in 1962–63. In his four seasons coaching the Comets, he squeezed the absolute best out of his undersized squad. Rollie concluded his high-school coaching career at Lexington High in Massachusetts, taking the 1964–65 team to a state championship. In 10 years at the prep level, Rollie compiled a 160–61 record.
Rollie coached two years at Stony Brook University on Long Island before joining Chuck Daly’s staff at Penn in 1972. In 1973, he was hired by Villanova University—a job he held for 19 seasons. In 1980, the Wildcats were inaugural members of the Big East Conference, which quickly became a hoops powerhouse. Though often outgunned, Villanova held its own against primetime conference rivals Georgetown and St. John’s during the 1980s. In 1984–85, Rollie had his greatest season, taking a third-place team into the NCAA Tournament and upending Dayton, Michigan, Maryland and UNC to reach the Final Four. The Wildcats featured a solid cast that included Ed Pinckney, Harold Pressley, Gary McLain and Harold Jensen. They defeated Memphis State in the national semifinal to set up a showdown with Patrick Ewing and the Hoyas. Rollie knew his team would have to play a perfect game to win, and it did, controlling the tempo and hitting 22 of 28 shots from the field—many on low-percentage shots and lucky bounces. The final score of 66–64 marked the greatest upset in the history of the tournament finals.
Rollie recruited successfully in the Philadelphia-to-Boston corridor. Among his best players was Rory Sparrow, who starred for Eastside High in Paterson. Rollie coached Villanova through the 1991–92 season and left with a 357–241 record. He moved to UNLV where he took over a program decimated by probation and the resignation of Jerry Tarkanian. Before he could turn it around, he was entangled in a salary controversy which resulted in his being forced out. Rollie spent the next seven seasons at Cleveland State, where his team was plagued by the off-field problems of his players and accusations of academic fraud. Rollie’s final college coaching job was at Keiser University, an NAIA school in Florida that later merged with Norwood University. Rollie led the varsity to four straight Sun Conference regular-season titles. The Seahawks snared NAIA Tournament bids in each of Rollie’s eight seasons at the helm, and made it to the national finals in 2012During his stint at Keiser, he was inducted into the Basketball Hall of Fame.
In 2016, Rollie was diagnosed with terminal lung and brain cancer. He not only lived long enough to watch Villanova win the 2016 NCAA Tournament, he continued coaching at Keiser against doctors’ orders and won his 800th game that December. NJ hoops legend Bill Raftery wrote and directed a documentary entitled The Maestro: The Rollie Massimino Story, which chronicled his final season. It aired in 2018, a year after his death at age 82.