Chuck Daly, who went on to become the head coach for two NBA championship teams and the head coach of the 1992 Dream Team, coached the Quakers from 1971-1975. What many people don’t realize, though, is that his right hand man for a few of those years was Rollie Massimino, who would go on to become a legendary head coach in his own right.
From 1971-1973, Massimino was an assistant coach for Penn men’s basketball. In 1973, Massimino leveraged his time under Daly to become the head coach at Villanova, where he went on to win a national championship in 1985 after leading the eighth-seeded Wildcats to a number of upsets. In 2013, Massimino was inducted into the College Basketball Hall of Fame to honor his success and contributions to the sport.
Prior to his time at Penn, the New Jersey native coached high school basketball. Over 11 years coaching at that level, he amassed a total record of 160-61, which led him becoming the head coach at Stony Brook University.
In his first season there, he led the team to a conference championship after going 19-6, which earned the school a berth in the NCAA Small College Tournament.
From there, Massimino transitioned to Penn in 1971. He entered along with Chuck Daly, replacing Dick Harter and Ray Edelman, who had a successful run during the the previous five years. Their last year at the helm spurred an Elite Eight visit for Penn in the NCAA Tournament.
Massimino was Daly’s assistant and right-hand man, as he took charge in many key aspects of the team.
"My assistant, Rollie Massimino, comes up with some of these defenses — he’s very inventive," Daly said in March of 1972.
On top of being what many referred to as a “master defensive strategist,” Massimino utilized his outgoing, boisterous personality to the team’s advantage.
“At this time, the last two years, I was pretty much tired of basketball,” Penn men’s basketball player Alan Cotier said at the time. “It’s different this year. Coach Massimino's the type of guy who’ll play pinochle in our rooms [on the road] at two in the morning. He’s a super guy.”
This “pinochle at two in the morning” style was something that perfectly complemented Chuck Daly’s more regimented personality. Daly was known for his stylish yet subtle leadership as head coach, while Massimino was known to yell, jump around, and bark orders during games.
“One thing that’s been so good is that Chuck and I have had a tremendous relationship together,” Massimino said at the time. “I relieve some of the burden he has. We really complement each other.”
This complementary style proved useful as a yin and yang dynamic, which spurred positive team relationships during their time together.
“[Daly and Massimino] were coming into a situation where they didn’t know anybody,” player Ron Billingslea said, “and they created an atmosphere of friendship which has carried through the whole year.”
The atmosphere translated into results, as Penn men’s basketball reached the third round of the NCAA Tournament in each of the years Daly and Massimino were together.
Then, in March of 1973, Massimino received an offer to coach at nearby Villanova. He accepted the job after putting it through the lens of his time at Penn.
“I was looking for a school comparable to Penn both educationally and athletically,” Massimino said upon accepting the gig.
After transitioning from head coach at the high school level to head coach at the collegiate level and then down to assistant coach in college, Massimino seemed to have no regrets.
“It was a very big decision for me to make, but if I had to do it over I would have done the same thing,” Massimino said at the time. “I’ve learned a great deal in the organization and structure of a major college. The people in the department have been really great to me.”
He would go on to coach Villanova for 18 years, securing 11 NCAA Tournament berths, six Elite Eight appearances, and one miraculous NCAA Tournament championship in the process. The NCAA Tournament championship came in the 1984-85 season when, as an No. 8 seed, Massimino led his squad to upset after upset to win one of the most shocking NCAA tournaments ever.
After his time at Villanova, Massimino made a few stops at different colleges with varying degrees of success. He passed away in 2017 at the age of 82 in West Palm Beach, Fla.
Daly and Massimino are both legends in the basketball coaching world. Each went on to great degrees of success, with Daly becoming one of the most illustrious NBA head coaches of all time and with Massimino securing his legacy with a historic NCAA Tournament championship. Both, though, had to make a pit stop at Penn before any of that could happen.
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