Sheppard’s greatest athletic accomplishment occurred before his senior campaign. In 1976, he was one of four Terps invited to the U.S. Olympic Trials. The other three were John Lucas, Brad Davis and Maurice Howard.
Sheppard trained harder than he ever had for a chance to compete on the world’s biggest stage. He used to complete a daily run from his home in New Carrollton to Cole Field House, spanning roughly 3.5 miles. He then would work on his basketball fundamentals and run back.
When the opportunity came, The Bear was ready. He made the final roster, coached by Dean Smith, which featured the best collegiate basketball players in the world. The U.S. went 7-0 and defeated Yugoslavia to win the gold medal. Sheppard became the first Olympic gold medalist in Maryland basketball history.
“I always used to love it when I watched the Wild World of Sports, and Howard Cosell and Frank Gifford would be on TV talking about world-class athletes,” Sheppard said. “When I was a kid, I wanted to be one of those. And then when you're down there in the Olympic Stadium, you think, oh my god, a kid from the Bronx is down here in the Olympic stadium. I’m a world-class athlete. … That was a heck of a feeling.”