Originally a standout Hampton Bays, NY surfer, Penny moved to Miami for his freshman year of college before transferring to San Diego State the following year. A naturally gifted surfer and standout in the water, Penny won the 1977 East Coast Championship. Determined to make big wave surfing his priority, in the mid-1970s Penny became one of the pioneers at Petacalco, Mexico and at Puerto Escondido, known as the Mexican Pipeline, and was featured in numerous Surfer magazine photos charging big surf.
Many years later, after being diagnosed with a deadly cancer and with only six months to live, Penny dedicated himself to riding the biggest waves possible. People still talk about him paddling out alone numerous times to Oahu’s North Shore outer reefs for XXL sessions that went without direct witness. In the pre-jet ski tow-in era, it was unheard of to do what Penny did. Surfing with abandon the last months of his life cemented his reputation amongst the North Shore big wave surfing community, earning Penny legendary status.