“I was like, ‘Hi, nice shoes,’” says Webb. That “corny” line didn’t earn him a date, and may even have put him in the self-described “friend zone” for a couple years. But it started the conversation. (These days Webb is back at U.Va. as director of health policy and equity at the medical school, and his wife, Leigh-Ann Webb, is a doctor too.)
The sneakers are more than just fancy footwear or an obsession. When Webb’s apartment burned down in medical school, he realized how much his collection meant. “I lost every pair of shoes I’d ever had,” he says. “It was heartbreaking.” When he eventually started buying again, he made sure to get another pair of Nike Air Max 97s, which hold a special meaning because of his fraternity. Decked out in gold and black, they bear the colors of Alpha Phi Alpha, the oldest Black fraternity in America.
Now that Webb is campaigning for Congress, he finds inspiration in his wide range of Jordans. His Airness was known for his clutch play in the fourth quarter. That’s a mentality Webb wants to emulate as he enters the October home stretch of his own race, trying to pull off a win for Democrats in a sprawling district that supported President Donald Trump by double digits in 2016.
“I don’t just buy any shoe or any colorway,” says Webb. “All the Jordans that I buy are because of something about an iconic Jordan moment.”
Take his “Georgetown” edition Jordan 11s, which represent the final minute of the 1982 NCAA championship. Or the Jordan Bred 4, which MJ wore in the 1989 NBA playoffs when he hit a game-winner simply known as “the shot.”