The teams were to meet in a first-round game in the 1987 NCAA tournament. Lefkowitz, now an executive vice president heading sales at FX and the National Geographic Channel, took the mike and offered an impassioned pre-game breakdown of Penn's chances.
"Everyone talks about this being a David-and-Goliath match-up," he said. "You know what, I checked their lineup and they don't have someone named Goliath and we don't have someone named David."
Once the nationally televised game tipped off, Lefkowitz's confidence had some credence. Penn somehow battled a loaded Carolina team to within two points at the half.
In the locker room, the 6-foot-8 senior exhorted his teammates, knocking things over and offering some version of "they're not that good."
Meanwhile, the Tar Heels' legendary coach Dean Smith may have some motivational tactics of his own in the other locker room. Within minutes after half, Penn's fortunes dampened swiftly and Carolina coasted to a 113-82 win. Lefkowitz (a.k.a. "Lefko") acquitted himself well, however, with 20 points and 8 rebounds in his last college game.
Lefkowitz had made another NCAA appearance as a sophomore that also had Penn facing an uphill battle. Yet, the Ivy League Quakers held a second-half lead before losing to Memphis State, which eventually made the Final Four.
Each year as March Madness begins, it doesn't take much for Lefkowitz to marvel at his good fortune to have played in an event that now has networks paying $10.8 billion to carry it and clueless IT geeks scrambling to get into the office pool.
"When you're watching, it brings you back and you realize what a unique experience it is and not a lot people get it," he said. "And so it puts you in a special class, a special fraternity."
On Madison Avenue, the fortunate may be limited to a trio. There's News Corp.'s Lefkowitz; Turner Broadcasting's Dan Merrifield, who played on the 1984 Final Four team at Virginia; and MTV Networks' Sean Moran, whose Ivy League champion Brown team qualified in 1986, but got crushed by Syracuse.
Understandably, CBS has tended to focus on the stars and teams that advance (as Merrifield's did) in its coverage of the tournament. But there are hundreds of players each year who get a taste and stories to tell for a lifetime, some on the business trail. In sales, how many CMOs would rather talk bracketology than budgets this afternoon?
Lefkowitz had people coming up to him for years wondering if he was the same guy who did some damage in the Carolina game, notably top media buyer Ray Dundas the first time they met. His Penn days led to a web of connections that helped land a job at Turner, which propelled him to a senior vice president's role at Discovery and now his top post at Fox Cable.
So as he has for years, over the next two days -- the glorious ones packed with afternoon games - Lefko will move his sales operations from the home office to a Manhattan watering hole. He'll join clients, friends and competitors for a viewing party and some occasional reflection. (Ya know, I'm telling you, if the ref hadn't blown that call, we would have pulled the upset and been Cinderella? A penultimate becoming a Penn ultimate.)
For the 46-year-old Lefkowitz, these two days follow Sunday's thrill of watching the annual "Selection Show" with his family - which brings the announcement of which teams will be in the tournament, and where they'll be playing.
He remembers that as a highlight of his NCAA experience. If the tournament means 60-plus teams will tip it up, the moment that your team is announced provides some exclusive bliss.
"You know every team in the country is watching," he said.
Lefkowitz's two NCAA tourney appearances earned him a pair of commemorative silver watches he doesn't wear much, but cherishes the chance to pass them on to two sons.
"I look forward to them having them and sort of carrying on those bonds with the tournament," he said.