He is known primarily for leading the Villanova Wildcats (near Philadelphia, Pa.) to a NCAA championship in 1985, despite entering the tournament as an 8th seed. Massimino's club pulled off one the great upsets in college basketball history by knocking off top-seeded Georgetown University (D.C.), 66-64, in the 1985 final. The road to the finals was even harder, starting with a win on the home court of #9 seed Dayton, then wins over #1-seeded Michigan, #4-seed Maryland with Player of the Year Len Bias, #2 North Carolina and Dean Smith, and then a Final Four victory over #2-seeded Memphis State, with the terrific Andre Turner at point and two NBA lottery picks in Keith Lee and William Bedford. He rejected a subsequent offer to coach the New Jersey Nets, claiming that he wanted more time for his personal life.

Massimino began his coaching career in 1962 at Hillside High School in New Jersey where he laid the foundation for his future college coaching successes. With the support of high school All-American, Bill Shutsky (who later captained the West Point basketball team) and others such as Paul Freider and John Maddalena, he led the Comets to the state Group IV finals in 1963 and 1964 against Central High of Newark in both seasons. Unfortunately, the Comets lost in both years to a team comprised of taller players.

Massimino began his coaching career in 1956 after graduating from the University of Vermont where he played varsity basketball for three years. His first three seasons he served as an assistant coach at Cranford (NJ) High school before securing his first head coaching job at Hillside (NJ) High School, his prep alma mater, in 1959.

From there he moved to Lexington High School, MA, in 1963 where he led one squad to a state championship and another to a 20-1 record, along the way laying the foundation for an elite scholastic program which has dominated the Middlesex League, winning state titles in 1971, 1972, and 1978 along with league championships in sixteen of the past thirty years. In 10 seasons as a high school coach, Massimino compiled a 160-61 record.

He debuted at the collegiate coaching level in 1969 as the head coach at the State University of New York (SUNY)-Stony Brook. His first team went 19-6, won the conference championship and earned a berth in the NCAA small college tournament. Massimino's next step was an assistant's position at the University of Pennsylvania under Chuck Daly, most recently of the NBA's Orlando Magic. In March 1973, Massimino left Penn to succeed Jack Kraft as the head coach at Villanova. Massimino has a master's degree equivalent in health and physical education from Rutgers University (1959) and a bachelor's degree from Vermont (1956) in education. Massimino and his wife Mary Jane have five children - Tom, Lee Ann, Michele, Roland (R.C.) and Andrew - as well as 16 grandchildren.

Eventually he coached at UNLV and Cleveland State University, never again matching the success he had at 'Nova. Noted for his "Family Style" coaching, Massimino is considered to be one of the greatest college coaches of all time. He is also a member of the Italian American Hall of Fame.

He repaired his relationship with Villanova, and is embraced by the school once again. He is currently traveling with the Villanova basketball team during the 2005-2006 season as part of Villanova's official traveling party.

He is currently the Director of Basketball Operations for the men's and women's team at Northwood University -Florida campus, a private school in West Palm Beach, Florida. He is coaching the Northwood University Seahawks. The 2006-2007 year will be the first basketball team the Northwood Florida campus (part of the NAIA conference, soon to be D.II) has ever had. Coach Massimino hopes to lead the team to their first ever NAIA basketball championship. One of the Seahawks first exhibition games will be against one of Coach Massimino's old teams, which he won a championship with in 1985, the Villanova Wildcats. A win against the Wildcats will boost the Seahawks' confidence for the years to come.