Wearing black cowboy boots with his suits—he's gone for two years without wearing dress shoes—and a serious yet genial demeanor, Cuccinelli calls himself an "endangered species," a conservative Republican who's won elections in Northern Virginia, the bluest part of the state.
"There's always been a fascination with his career because he would hold views and win elections in a way people thought was impossible to do," says Holsworth, who chairs Governor McDonnell's committee on redistricting.
Cuccinelli was a patent lawyer living in Centreville in 2002 when he decided to run in a special election for a state Senate seat in western Fairfax, the most Republican part of the county, where the GOP incumbent was leaving office.
His primary opponent had the backing of the Republican establishment. Cuccinelli went down to Richmond to ask for the endorsement of former Virginia GOP chair Patrick McSweeney, a leader of the party's right wing. "I said, "Who's endorsed you so far?"" McSweeney recalls of his first meeting with Cuccinelli. "He said, 'No one. I'm going to run anyway.'"
Cuccinelli campaigned tirelessly with door-knocking, phone calls, church appearances, a big personality, and a fierce anti-tax, anti-abortion message.
Fewer than 2,000 votes were cast in total at Robinson Secondary School, the single polling place for the primary. At the end of the night, Cuccinelli drove off in his uncle's rusty '84 Isuzu pickup truck with the win.
He went on to beat the better-funded Democratic nominee after leading the charge against a proposed tax increase for transportation that had wide support in the Virginia General Assembly.
"That election shaped my attitude about Ken—how gutsy he was and how highly principled," says McSweeney. "He was willing to lose for the right reason."
In the legislature, the 34-year-old quickly earned a reputation as an energetic, engaging, and whip-smart politician who would often point out procedural missteps to his elders. Yet he was so unbendingly conservative that he annoyed the more moderate leaders of his party, who often dismissed him and thwarted his initiatives.
"I paid little or no attention to partisan efforts by him," says John H. Chichester, the retired GOP chairman of the finance committee.
Cuccinelli admits that his biggest fights were with his own caucus.
"The culture of the senate in the Virginia legislature is to eschew the extremes and cleave toward the middle," says Chap Petersen. "Ken did not buy into that culture."
During his seven years in the Senate, he gnawed at the usual conservative thorns, becoming a reliable opponent of abortion, higher taxes, illegal immigration, and same-sex unions. He wanted Congress to amend the 14th Amendment to the Constitution to deny citizenship to those born in the United States whose parents were illegal, and he supported the creation of choose life license plates to fund anti-abortion efforts.
Though colleagues considered him a fringe player, voters seemed to appreciate his firm convictions and, with the help of a loyal base of social conservatives, reelected him.
"He's not afraid to take a position," says former Democratic governor Douglas Wilder, who considers Cuccinelli a friend. "People like that. They don't want to see a finger in the wind."
Another part of Cuccinelli's success, say observers, is his likability. With a quick wit, even temperament, and quirky sense of humor—he's a big Monty Python fan—he comes across as not unreasonable. It's what makes him especially effective, say admirers. And especially dangerous, say detractors.
Next: Cuccinelli files the first law suit against Obamacare