One thing. I don’t believe Penske ever drove in NASCAR (at least not that I can recall in my 20 years of watching) but he has been involved as an owner for a long time. In fact he is really the man who made Michigan International Speedway a success.
Penske entered the 1963 NASCAR Grand National Series in 1963, winning five races driving a Corvette Chaparral GS. In 1964, Penske set the motorsports world on fire. Competing at the Bahamas Speed Week, he drove a Corvette Grand Sport to win the Nassau Tourist Trophy. He then drove a Jim Hall Chaparral to defeat contenders Bruce McLaren, Dan Gurney, and A. J. Foyt for the Nassau Trophy. He retired from racing at this point, buying a Chevrolet dealership in Pennsylvania. He returned to racing briefly, entering the 1966 Sebring race in a Corvette Grand Sport.
Penske did, but retired in 1965, which is probably why you don’t remember him.
Penske was a contemporary of Fireball Roberts, and if you know about Roberts, then you also know about Smokey Yunick, his manager.