Rolling in his black Silverado pick-up, we drive around West Tampa for a while. Webb grew up here as Henry Ruiz (he changed his name professionally in 1969 at the request of a station manager), born to Cuban and Spanish parents who were themselves born in Ybor City, where their families worked in the cigar factories. Though noticeably dangerous and abandoned now, West Tampa was more or less safe when he was young. Asked if there was much violent crime back in the day, Webb only points to an outlying incident from when he was five, and was standing just feet away when a schizophrenic neighbor blew his wife's brains out for imagined infidelities. "It sounded like a watermelon exploding," he says. "She dropped like a prom dress."
Finally, we stop at his friend Danny's house. One of Webb's childhood friends, Danny is a classic bleeding-heart eccentric, right down to the long hair and red Hawaiian shirt. Together, as kids, they rooted for the Baltimore Colts — the only team they used to get on television — and then for the Buccaneers after they came to town in 1976. Later on, during the cutthroat radio wars of the 1980s, Danny was a regular guest caller on Webb's long-running sports show. Today they're arguing about ObamaCare — Webb questions its reallocation of funding, while Danny has faith in the program. But they also agree on a few things: Ann Romney's RNC speech sucked, and former Florida governor Charlie Crist, according to Webb, has "more positions than the Kama Sutra." Their only real point of tension comes when Webb predicts that Mitt Romney will win the presidential race. "America has always voted with its pocketbook," he says. "Nothing else matters."
Tedd's unique in his brand of conservativism. He doesn't just support weed — he smokes it. He drives American-made trucks, but Japanese cars, and fears the growing deficit not just because he has three kids and four grandchildren, but because "it will lead us into war." Webb thinks it's wrong to demonize the likes of Bain Capital (Clear Channel Communications, a Bain company, owns his current station); at the same time, however, he admits that the industry was "more fun when it was run by moms and pops."
If one thing especially separates Webb from the right-wing pack, it might be his interest in astrology. He first studied the star map in 1970, when he had a local psychic named Paige Bryant on his show, which was then on the St. Petersburg station WFSO. He was reluctant to listen, but softened up after she asked if he'd injured his ankle. Two years earlier, while serving in the Air Force during Vietnam, Webb had indeed twisted his leg while playing football on a base in Michigan. Months later, he learned how to read charts and sniff destiny. Though he laughs when I ask if the galaxy guides his grand philosophy, his faith in the stars at least reflects his view of independence. "It's not like predicting the future," he says. "You always have free will, but I can tell you when there might be certain times that you shouldn't be doing certain things, like driving too fast, or falling in love."