RICH TARRANT Photograph by David Seaver.

At 63, Tarrant remains a towering figure; standing 6 feet, 6 inches, he is easy to spot in the crowds as he shakes hands at barbecues and spaghetti dinners across his state. His campaign promises feature plans to improve national health care through a free market-based Medicare system, curbs on federal spending and ideas to boost economic growth in rural areas. "I need a podium or platform to do that," he says. The chance to mount such a platform appeared when Jeffords, a former Republican who became an independent in 2001, announced last year that he would retire from the seat after three terms.

Although Vermont has a historical tradition of sending Republicans to Washington, Tarrant’s campaign is seen as a long shot. His rivals and the press have excoriated him for his affluent lifestyle, which goes over poorly before an electorate made up of thrifty Yankees, despite his attempts to downplay it. At public events, he usually dresses casually and was rarely spotted in a tie this summer, as he crisscrossed the state, hosting a spaghetti dinner in Hardwick, a pizza lunch in Rutland and stopping by for a photo op at BJ’s gun shop in Williston.

ILLUSTRATION BY Tim Bower.

But voters found out Tarrant leads a more lavish lifestyle at his second home in Florida than he does in Vermont. Peter Freyne, a columnist for Seven Days, an alternative newspaper in Burlington, made an issue of Tarrant’s Bentley, which he houses in Florida. "His style is such that when 90 percent of Vermonters see the size of his houses, the amount of money he made—they just don’t identify with him," maintains Eric Davis, a professor of political science at Middlebury College. Tarrant, for his part, seems annoyed that he must answer for the way he lives. "I am what I am," he declares. "I don’t apologize for being successful."

Despite this, Tarrant’s biggest challenge is not establishing his Vermonter credentials in the minds of voters, but gaining the political credibility needed to beat his Democratic opponent. If he captures the Republican primary (Boston College’s Steen found that self-financing is more successful in primaries than general elections), he will face an opponent in Sanders who, although he was born in Brooklyn and still displays hints of an accent, is so familiar that Vermonters refer to him simply as Bernie. Tarrant’s local roots, wealth, entrepreneurial credentials and folksy manner may not be enough to offset the popularity Sanders has built during his 16 years in Congress. Indeed, Davis believes Tarrant has little chance against Sanders; many Vermonters see him as something of a reverse carpetbagger. Some speculate that, if Tarrant loses, he will retreat south to Florida. The candidate himself remains inscrutable on this point, responding tersely, "I don’t think about losing."

Strife of Interests
Those who run successful self-funded campaigns face an array of additional challenges, as Mark Dayton can attest. Dayton, a Democratic senator from Minnesota, was so motivated to advance his liberal political agenda that he self-funded two campaigns before finally winning his seat in the Senate in 2000.

Dayton’s family fortune is rooted in the Dayton’s department store chain (now part of Federated Department Stores), which gave him the advantage of name recognition. He also had public-sector experience, having served as popularly elected state auditor and as legislative aide to Minnesota favorite son Walter Mondale.