The Lehigh University-trained engineer was so determined to be an automotive journalist that in the 1990s he twice worked as a gofer just to be around Ann Arbor-based Car and Driver. He finally landed a writing job there, starting a rapid rise that culminated in 2012 when the Hearst chain moved Road & Track here from California and asked him to run it.

Webster revved up the moribund monthly with talented writers and a sleek new design. Yet in February he walked away. He’s now commuting from Ann Arbor to Traverse City to work for Hagerty, which most people know only as an insurance company.

It’s not the comedown it seems.

One of Webster’s first articles on began, “Thank you, crazy car people!”–Jerry Seinfeld’s greeting to the crowd at a vintage car auction prior to a March show at Amelia Island, South Carolina. The comedian had eighteen cars up for sale, Webster wrote, so he asked Brian Rabold, Hagerty’s VP of Valuation Services, “what’s the ‘Seinfeld Multiple?'”–that is, how much more is a car worth because it was owned by Jerry Seinfeld? “Twenty-five percent,” Rabold grinned.

“The truth is that the multiple is tough to nail,” Webster added. While some of Seinfeld’s cars brought more than the auctioneer’s estimate, others fell short. The most valuable, a Porsche 917/30 racer, sold for a whopping $3 million. But his 2000 Porsche Carrera GT didn’t get a single bid. Still, as Webster wrote, “he pocketed $22.2 million. In two hours.

Prices like that explain how company CEO McKeel Hagerty could afford to hire one of America’s best automotive journalists. Hagerty has built his hometown company into the world’s largest specialty provider of insurance for classic cars–and as vintage car prices have escalated, so has its revenue.

While insurance is still his core business, Hagerty explains by phone, “We really positioned ourselves long ago … to be the source for collector car owners to be able to figure out what their cars are worth.” Now he wants Webster to help build a sense of community among the company’s nearly one million clients in North America.

“I think that as much as the popular media world out there seems to be predicting the death of the car, my view is that there’s still this very faithful tribe of car people who want to still have great resources [to learn about cars], still want to have a lot of fun with cars, still want to own them, still want to drive them.”

He wants Webster “to help create the magic,” Hagerty says. “What are the stories people want to hear? What are the activities that we ought to be championing? What are the driving events we ought to create? … He gets to be the medicine man of the car world.”

“I’ve been a customer of the company for a long time, and I love all they do for car nerds like me,” says Webster, returning a call while driving up to Traverse City, where he stays at his wife’s family cottage. “I got the chance to help enable that passion … it’s kinda simple.”

Webster says that he and Hagerty were often at events together, from car shows to races. They also “share an interest in riding bicycles, so when I’ve been up north, we’ve ridden. He approached me and said, ‘I’d like you to do this for us … what do you think?’ I said, ‘I think this is pretty great.'” As VP of Content, he’ll be in charge of Hagerty Classic Car Magazine, the Hagerty Price Guide, their online presence, and video. The magazine alone reaches 450,000 people per issue–and while Hearst had no interest in growing Road & Track’s circulation, McKeel Hagerty says he’s adding 150,000-200,000 new customers a year to engage in his community of car nuts.

Csaba Csere hired Webster atCar and Driver when he was its editor-in-chief and has known him ever since. He’s got an industry veteran’s perspective on his former protege’s surprising move.

“I think being editor of Road & Track is certainly a dream job but not as dreamy as it was twenty years ago,” Csere says. “The reality is, Hearst is a giant publishing company and R&T was one of its smallest, if not its smallest and least profitable, magazines. So in the Hearst ocean, [Webster] was a minnow.”

While being at Hagerty will be “different from working for a magazine, it’s still kind of working with car nuts,” Csere says. “He’s going to work closely with McKeel, who runs the operation, where at Hearst he was probably four or five rungs down from the top guy–and the top guy was in New York.”

Kim Wolfkill, who succeeded Webster as editor of Road & Track, came from Microsoft, where he worked with car companies whose machines appear in the Xbox game Forza Motorsport. But he’s no stranger to Road & Track–at the turn of the century he ran the editorial side of, and in the mid-2000s he was a senior editor at the magazine.