But when Wehner arrived on the Vineyard, his life was far from luxurious.
It was 1994, five years after he had been released from the Baltimore County jail on drug conspiracy charges. He camped in a tent on the island for five weeks before finding an apartment.
Wehner fixed mopeds by day and worked as a sous chef at night. But soon he spotted a new market to tap: summer residents who were sending their foreign cars to the mainland for repairs.
Wehner, who had learned to work on cars in Baltimore, opened a business that he said grew into "the second-busiest shop on Martha's Vineyard for eight years."
He also developed contacts who would become some of the founding partners of Baltimore's Grand Prix.
His Vineyard friends rallied around Wehner when he tried to expand his repair shop into a gas station. A lawyer, a traffic engineer, and several financial backers helped him fight the island's government for permission to open the station.
The costly — and ultimately unsuccessful — legal battle eventually led to him to close the shop.
But the relationships that were strengthened during the failed court case would prove key to the birth of Baltimore's Grand Prix. When the defeated Wehner came home to Rodgers Forge and hatched his plan, he would call on his island friends for help.
A 'wild idea'
On a brisk morning in February 2008, Bill Cole sat in Mt. Vernon's City Cafe listening to Wehner pour out his grand idea in a torrent of words.
Wehner was so anxious he didn't touch his cream of crab soup.
"He was a nervous wreck," recalled Cole, who had joined the City Council two months before.
As the representative of the downtown area, Cole often meets with dreamers with lofty visions for the city. He wasn't a fan of auto racing; he wondered at first if Wehner were pitching a foot race.
It "seemed like the kind of wild idea you get all the time," Cole said. "I said, 'I don't know what to tell you, but I really don't see how this will work.'"
Cole had agreed to meet with Wehner at the request of a friend and fellow politician.
Keiffer J. Mitchell had lost the Democratic mayoral primary months earlier to Sheila Dixon. A friend had connected him with Wehner, who, like Mitchell, was a "B.L. guy" — a graduate of the private Boys' Latin School.
Mitchell soon became one of the Grand Prix's great champions, and, within a year, a partner in the company that Wehner founded to organize the race. Although Mitchell stepped away from the group after winning a seat last year in the House of Delegates, he retains a 1 percent share in the company.
The meetings with Mitchell and Cole were the culmination of more than two years of research and preparation by Wehner.
He says he became convinced that the Inner Harbor was the perfect setting for an Indy-style race, which he believed would reap big profits while presenting a new image of the city to the world.
All I heard about is 'Homicide' and '[The] Wire,'" he said. "You go to Green Spring Valley, Valley Road. That's Baltimore. You go down to the Chesapeake Bay, that's Baltimore. … That's what the nation needs to know.