Herman Cain likes to brand himself as a political newbie.

“Hello, I’m Herman Cain. I am not a politician. I am a problem-solver with over 40 years of business and executive experience” were his first words at the June GOP debate. In an interview with CNN last week, Cain said, “I am not a Washington insider, and I’m not a politician, even though I have helped other politicians relative to their campaigns. . . . So I consider myself not only a Washington outsider, but also a non-politician, because even though I have helped people, I have not held high elected office.” And during the CNN debate last week, Cain touted his non-Washington brand again, describing one of his views as “another one of these bold ideas by the non-politician up here.”

Cain’s marketing smarts are no secret. And it’s clear that he sees his non-politician status as a crucial asset enabling him to woo voters. In a cycle when voters view “Washington” warily, Cain’s outsider image has a unique appeal.

Left unsaid: Although Cain may be no fan of the ways of Washington, he’s been considering for a long time how to get there. Cain’s failed 2004 Senate bid is well known, but his other political forays have remained outside the spotlight.

For at least 15 years, Cain has been considering a presidential bid. “I might even run for president,” a grinning Cain told the Omaha World-Herald in 1996 when discussing his political aspirations. He began considering a Senate bid even earlier: A 1995 article in Restaurant Business magazine reported that Cain had ultimately decided not to run for Senate in 1994, but “the registered Independent from Nebraska hinted, ‘You should not be shocked if I were running for some kind of public office.’”

Cain served as a senior adviser to the Bob Dole–Jack Kemp campaign in 1996. An incident during that campaign led to his pivotal decision to switch his registration from independent to Republican: When in Harlem with Kemp (en route to a campaign stop), Cain was called an Uncle Tom by an African-American man. “I felt anger,” Cain told the Omaha World-Herald. “That’s one of the biggest insults one black can give another, to accuse him of being an Uncle Tom.” The man’s assumption that Cain was a Republican — and that to be a Republican was to betray his racial heritage — rankled Cain, and was the tipping point in his decision to register as a Republican. “I believe in the platform of Dole and Kemp. That’s why I registered as a Republican after that guy ticked me off,” Cain told the World-Herald.

Interestingly, before Cain became a senior adviser to Dole, he was viewed as a possible vice-presidential candidate. “Mr. Dole’s advisers have taken to throwing out some essentially unknown (and arguably less-than-qualified) candidates, if only to stir the pot a little,” the New York Times reported. “What about Herman Cain, the charismatic president of Godfather’s Pizza in Omaha, who caught Mr. Dole’s advisers’ eyes by challenging President Clinton on his health care plan at a televised town meeting?”

Cain’s decision to become president and CEO of the National Restaurant Association that same year allowed him to start developing relationships with Washington insiders. It also resulted in his having a presence in Washington: The World-Herald described his office there as “a room decorated with a framed newspaper picture of himself and Newt Gingrich and a sign inscribed: No Whining.”

In 1997, the Lincoln Journal-Star reported that Cain was considering running either for governor or for Congress. “I am giving some careful consideration to it,” Cain said, “not because it’s been a long-term aspiration, but because I feel so passionate about the problems that we face in our community, state and country.”

But Cain then shifted to considering a presidential run, according to a December 1998 Associated Press article. “Nobody expected Jesse Ventura to win the governor’s race of Minnesota,” Cain said, making the case for his electability. “What I want to accomplish doesn’t require me to go out and raise a kajillion dollars.” In February of 1999, Cain was talking to friends and family about whether he should run for president, according to the Omaha World-Herald. National Journal ran an article in March headlined “From Pizza to K Street to President?” that looked at a possible Cain presidential candidacy.

By May, the speculation had reached a point where Restaurant Business felt obliged to weigh in with an editorial that urged Cain not to let his presidential aspirations distract him from his job at the National Restaurant Association. “Please, Herman, don’t compromise all the good you’ve done for the association and the industry by taking your eye off the ball,” Restaurant Business wrote. “Either make a decision soon, and settle the matter once and for all, or wait until November [when his term at the NRA would be up].”

So serious was Cain about a possible bid that, as the Des Moines Register reported, he visited Iowa in April of 1999 “to tell top state Republicans he is considering a bid for president in 2000.” He said he was thinking about running because “there isn’t the leadership to solve the [nation’s] problems” and he was concerned that “the message of the Republican Party is not focused enough.” He also traveled to New Hampshire and even formed an exploratory committee, according to the Omaha World-Herald.

In mid-May, Cain decided he would not run, for reasons that may surprise those skeptical about the amount of organization behind his current campaign. “The two biggest things I had not anticipated was how long it takes to build an organization and how long it takes to raise the money,” Cain told the Omaha World-Herald. Running for president is “not practical.” Instead, Cain served as the national co-chairman for Steve Forbes’s 2000 presidential run.

But even in 1999 Cain was confident he could run a successful campaign. Asked by the Des Moines Register during his Iowa visit how his campaign would be different from the prior failed campaigns of businessmen such as Ross Perot and Morry Taylor, Cain — who’s become famous for his simple 9-9-9 tax plan — knew what would make him different.

“Maybe they didn’t do a good job of articulating their message,” he said.

— Katrina Trinko is an NRO reporter.