Washington (CNN) -- In late 2012, when Neel Kashkari first pondered the idea of running for governor of California, one of the first people he sought out for advice was another Republican who once faced long odds in a big state gubernatorial bid: George W. Bush.
Bush was an underdog when he tried to unseat Texas Gov. Ann Richards in 1994, and he ended up winning in that year's GOP landslide.
He went on to the White House, of course, and was in the waning days of his presidency in 2008 when the world's financial markets were teetering on the brink of collapse. It was then that Bush looked to the Treasury Department — and Kashkari — for help.
Kashkari was the 30-something whiz kid engineer-turned-banker-turned-bureaucrat working under Treasury Secretary Henry Paulson to shape the Troubled Asset Relief Program, better known as TARP, the $700 billion Wall Street bailout that helped avert a global financial calamity. Kashkari then left Washington with his wife, engaged in some emotional detox in a rural northern California cabin, and later joined the investment firm Pimco.
Four years on, the markets humming, Kashkari traveled to Dallas and sat down with the ex-president. He asked Bush why he had the confidence to run against the tough-to-beat Richards.
"He said, 'The facts were on our side.' He thought that she was light on the subject of issues. He was going to focus on the real issues facing Texas as the time," Kashkari recalled.
Bush had some other convenient facts on his side, mainly a famous last name and a state that was trending politically in his direction. Kashkari can't say the same.
A smurf against Gargamel
As he mounts a long-shot bid against California Gov. Jerry Brown, barely anyone believes he can win in the deep blue state, even in a midterm year that looks more and more hostile toward Democrats. Kashkari himself expresses some honest skepticism about the enterprise. He recently compared himself to a smurf, and Brown to the evil wizard Gargamel.
After announcing his campaign in January, Kashkari is polling at a paltry 2%. Not only is he trailing Brown by 45 points, but he's also trailing Tim Donnelly, a tea party Republican who was once a member of the Minuteman movement, by 7 points. Second place matters in California's nonpartisan primary system, in which the top two finishers square off in the general election.
Plenty of candidates embark on long-shot campaigns against powerful incumbents, but many of them are small-timers, amateurs, ideologues or hucksters. Kashkari is none of those things, which makes his upstart candidacy all the more perplexing.
Today, Kashkari is 40, still youthful and brimming with restless energy. As a candidate, his profile is appealing: A Midwest native and the son of Indian immigrants, he has a degree from Wharton and worked for Goldman Sachs before joining Paulson at Treasury. In 2008, People magazine named him one of the sexiest men alive.
"I play to win at everything I do," he says. "I always talk about having two goals. Goal number one is to win. Goal number two is help rebuild the Republican Party in a positive, inclusive direction."
The simple theme of Kashkari's campaign is typed out on his Twitter bio. "Jobs and Education. That's it! I'm Neel Kashkari and I'm running for Governor of California."
If Kashkari somehow pulls off a miracle and topples Brown in November, it would bring an end to one of the most storied, unlikely careers in American politics.
An ambitious legal and policy wonk, Brown was just 32 years old when he was elected California secretary of state in 1970. He went on to serve as governor (1975-1983), mayor of Oakland (1999-2007), attorney general (2007-2011) and now governor once again — with one losing Senate campaign, a stint in Japan studying Buddhism, and three ill-fated presidential bids sprinkled throughout his lengthy career in public life.
Using Brown's record against him, kind of
Kashkari is trying to use this long record against Brown, employing a questionable rhetorical trick in the process.
"This guy has had his hands on California for the most part of 40 years," he says. "In 1980, California had the 11th most educated population in America. We're 48th today. You couldn't engineer that decline if you tried. In 1980, we were about 25th for jobs. As I said earlier, we're 47th today. In 1980, we were around 25th for poverty, today we're No. 1 in poverty. Literally, the last 35 years have seen the destruction of the middle class in California."
Left unsaid: Since Brown ended his first tenure as the state's chief executive in 1983, Republicans have governed California for 23 of the last 30 years. Brown's GOP predecessor, the cigar-chomping Arnold Schwarzenegger, left him with a $25.4 billion deficit when he returned to office in 2011.
With the help of a 2012 ballot measure that increased taxes on the rich, Brown transformed the budget hole into a more than $4 billion surplus. It's a centerpiece of his "California Comeback" story.
Brown's record is not spotless. Unemployment has dropped, but at 8%, it's still the fourth worst in the country. A Census Bureau report last year showed that nearly a quarter of California's 38 million residents live in poverty: the highest rate in the country.
With pension obligations and a huge public employee sector, California still faces enormous debts. And the governor has been relentless in pushing for the construction of an increasingly expensive bullet train from Los Angeles to San Francisco. Kashkari has dubbed the high-speed rail project, which is opposed by a majority of Californians, "the crazy train."
Canceling the train is one plank of Kashkari's economic plan. He also wants to give tax breaks to companies moving to California, implement a suite of regulatory reforms, and open the state's untapped oil and gas reserves to hydraulic fracturing, which he says is a surefire way to create jobs.
Education is the other policy issue that motivates him. He has solicited input on the matter from Jeb Bush, the Republican Party's reigning wise man on education policy.
"A growing economy combined with a failed education system means people who get that lousy education are falling behind and those of us who are getting that good education ride that growing economy to the top and income inequality expands," he says.
Yet to air a television ad
Before Kashkari can have an honest hearing on the issues, voters have to know he actually exists. That's a daunting task for an underfunded candidate in a state so vast and expensive as California.
Running a respectable statewide television ad campaign for one week, spanning media markets from Sacramento to San Diego, can cost as much as $2.5 million at a minimum. With two months to go before the June 3 primary, in which the top two finishers advance to the general election, he has yet to air a television ad.
With his ties to Wall Street and Washington, Kashkari has something of a built-in fundraising network. He has collected campaign checks from Hank Paulson and top tier GOP donors like former Univision chairman Jerry Perenchio and cell phone pioneer Craig McCaw.
Kashkari has raised $1.3 million since joining the race in January, a respectable sum. But this is California, and his opponent is an incumbent governor. Brown is sitting on $20 million.
"We've got to do this on the cheap, so we're looking at a lot of different ways of reaching our audience," Kashkari says, plugging his digital operation.
Brown's advisers, more than comfortable with their position in the race, chuckle when asked about Kashkari. Brown is not only an incumbent, after all, he's a Democrat in a state President Obama won by more than 20 points in the 2012 election.
After reminding a reporter that Kashkari still trails tea party candidate Donnelly in primary polls, it doesn't take long for Brown's aides to bring up the disastrous 2010 candidacies of Meg Whitman and Carly Fiorina, a pair of credible, business-minded Republicans who got thumped in their respective gubernatorial and Senate campaigns after they underestimated the state's Democratic bent.
"We've seen this movie before," said Brown adviser Dan Newman. "There's a sad history we have in California with these wealthy first-time candidates who run self-indulgent, ego-fueled, vanity campaigns."
Running on TARP?
Then there's the whole TARP thing.
"Bailout Architect Runs For California Governor; World Laughs," read one Rolling Stone headline after Kashkari launched his campaign.
"His whole reputation is based on the one policy act of handing out hundreds of millions, sorry billions, of dollars to Wall Street banks," Newman says, his glee barely concealed.
Kashkari has gamely tried to transform his experience during the financial crisis, memorably captured in the book and HBO film "Too Big To Fail," into an asset.
"Not only did we protect the taxpayers and make a $13 billion profit, which has never been done in American history, we did it in a completely bipartisan manner," he explains. "So we got all the leaders of the Republicans and Democrats to work together, put their country before their political careers. Honestly, that's the foundation for why I'm doing this. I feel like if we can get them to work together in Washington, though they're not right now, but they did at that moment, then we can get them to work together in Sacramento."
Michele Davis, a senior Treasury Department official who worked alongside Kashkari during the drama, said the experience showcased his type-A determination.
"Neel was the one who was willing to go up to Congress and take all the slings and arrows," she said. "Nobody wanted to do that. That took a lot of backbone, to be the face of it."
Davis, though, said she and her colleagues from the Bush administration were more than a little surprised by Kashkari's decision to leave Pimco and run for an almost unwinnable office.
"After the first initial 'What in the heck?' reaction, it's like, good for him that he's found something he's passionate about it and he's going after it," she says. "Not everyone is willing to drop everything on a long shot, and that's really admirable."
Kashkari is unusually candid about his chances.
With Democrats outnumbering Republicans in California by a wide margin, Kashkari admits he has to count on winning pretty much every Republican vote as well as a big majority of independents while peeling off a healthy chunk of Democrats. In short, Brown will have to flame out in spectacular fashion.
"I will sleep well at night if I run the campaign that we are running, which is a campaign that I'm proud of, because we are focusing on issues that matter and we run an honest, authentic campaign," he says when asked if he's comfortable with the long odds he faces.
A thought experiment
This is where the thought experiment aspect of Kashkari's campaign comes in.
Last year, before he formally declared his candidacy, he spent the year visiting low-income neighborhoods, churches, homeless shelters and Latino communities.
"I'd go by myself," he says. "There were no cameras, no staff. I'd say, 'I want to learn what your life is like. I want to learn what the challenges are.' Two things amazed me. Number one, people couldn't care less that I was a Republican. It never came up. Utterly irrelevant. Number two, people didn't want welfare, they just wanted a job. What's exciting to me is that I think that I can reach a very diverse group of voters in a way that few Republicans have done in recent years."
Kashkari and his advisers have been upfront about the fact that win or lose, he is running, in part, to help repair the party's tarnished image among young people and minorities. He boasts that the first television interview he did was with Univision.
"Neel turns the perception of Republicans on its head," says his consultant Aaron McLear. "Now we're the inclusive party running a young minority candidate fighting for the middle class."
Even though it might alienate some of the state's conservative voters — and there are still plenty in California, where the state Republican Party has become dominated by tea party hardliners in recent years — he's wiped social issues from the agenda, a political necessity on the culturally liberal Pacific Coast.
"'Im socially libertarian," he says. "I'm pro-choice, no problem with same-sex marriage. ... A 35-year-old Google engineer looks at you like you're from another planet if you don't share their views socially."
Kashkari has sought counsel from a variety of prominent Republican leaders who don't share those views, including the Bush brothers. He has huddled with Tennessee Sen. Bob Corker, talked budgets with Mitch Daniels, and named Chris Christie and Scott Walker as two GOP governors he admires. After an interview with CNN in Washington, he made his way across town to meet with House Budget Chairman Paul Ryan.
"I think my candidacy is viable in California, but I recognize this is not a model that, today, would play nationally," he says. "We're trying something in California, and I'm hoping that we can show that California can lead the country in a positive way by showing there's an interesting new profile of a young Republican leader."