Alan Grayson, D-Fla.

“Populism is popular,” Grayson told the Washington Post in October. The congressman has, since coming to the House, formed a tight working relationship with Rep. Ron Paul, Republican of Texas. They share an entrepreneurial approach to politics — and the same reputation for quirkiness. Grayson’s mission echoes Paul’s: to peel back the secrecy of how power works in the United States by asking fundamental questions.

Grayson is particularly interested in finding out who, at any moment, is getting screwed. Bronx-raised and Harvard-trained, he litigated the first case in which an American contractor, Custer Battles, was held responsible for bilking taxpayers in Iraq. He made millions. On the Hill, Grayson has set his sights on the immensely powerful and somewhat impenetrable Federal Reserve, the object of Paul’s long scrutiny, too. Grayson worked the House floor to get “Audit the Fed” language considered, pressing members to sign on as co-sponsors. Some 320 eventually did, and a watered-down version of the provision survived last week’s House-Senate financial reform conference committee. One conservative Florida activist, Sarah Rumpf, an active player in Republican politics, generally talks about Grayson as if he were, well, a maniac; his sometimes bumpy interactions with constituents on trips home she likens to “going to someone’s house, insulting their decorating, hitting their kid, and leaving.” And yet she says of Grayson, “You know, he’s right that the Fed is a big, hot mess.”

To stay in Congress, Grayson has to win down in the Florida 8th in November. It’s shaping up to be a fairly insane election. Nonpartisan analyst Charlie Cook rates the district as leaning slightly to the GOP. Grayson’s win last time around came at the expense of a weak opponent, in a year when it was very good to be a Democrat, especially in Obama-crazy Orange County.

Working for Grayson is the fact that the Florida Republican establishment is, itself, a hot mess. Republican activists blanched at having Charlie Crist shoved down their throats as a Senate candidate, and there are similar independent strains at play in Grayson’s district. Conservatives argue this is partly Grayson’s doing. There’s a controversy raging over whether Grayson is behind the establishment of the Tea Party as an official party in the state; it is fielding a candidate not only in Grayson’ race, but in contests across the state. Critics allege that Grayson’s plan is to peel a few votes away from conservatives in tight general elections, including his own, where Peg Dunmire is on the ballot on the Tea Party line. Jurkowski scoffs that it’s “a fabricated controversy,” from Republican establishment figures “who hate anyone not like them” — whether it’s grass-roots conservative activists, or Alan Grayson.

Complicating the Aug. 24 GOP primary (Grayson is unchallenged in the Democratic primary) is that the party establishment’s candidate — a former state legislator named Daniel Webster — originally opted out of the race, only to reconsider and jump in with the support of big-name figures like Jeb Bush and Mike Huckabee. But this didn’t clear the GOP field. Some grass-roots activists prefer Pat Sullivan, a local tea party (rather than “Tea Party”) organizer in North Lake. Über-conservative Dan Fanelli also has an online following; one incredible ad spot shows him gesturing to a white-haired white guy and asking, “Does this look like a terrorist?” before turning to an Arab-looking gent and asking, rhetorically, “Or this?”

Grayson, seeing an opportunity to stick a finger in the eye of squabbling conservatives, recently released a self-commissioned poll that found him to be the most popular candidate were he to run in the Republican primary. Not that he’d accept their nomination, he mischievously noted. “The Republican Party is about as popular as food poisoning.” Asked to assess the state of the race, Jurkowski, his spokesperson, says, “We’re either delusional or things are going well.”

With Grayson such a juicy target, Rep. Pete Sessions, the chairman of the National Republican Congressional Committee, recently made a trip down to Orlando last month for a “Pink Slip Party” on the steps of City Hall. It was aimed at Grayson and a Democratic congresswoman from a nearby district. The turnout was, judging by news footage, meager. But the message was still a challenge to Grayson: Forget the bickering and infighting; Republicans at the national, state and grass-roots levels would unify behind whoever proved to be the strongest challenger to Grayson in the fall. Still, for now, at least, Grayson has far more campaign cash than any Republican running. There’s very little chance that Grayson, especially with his deep personal wealth, will be outspent. But a united Republican attack could even the playing field considerably.

What gets conservatives fuming around Grayson is, in part, how liberals around the country have claimed him as a hero. “Alan caters to them,” Sessions told the Orlando Sentinel. “He’s the darling of the left.” Jurkowski framed his boss’s approach the same way. Grayson does play the traditional political game of bragging about how much money he’s brought back to his district. But when his team talks about their ideal audience, it’s defined more by archetype than geography. “They,” says Jurkowski, “don’t need a 20-second sound bite or cable news or even local news, when they can find it for themselves on the Internet and make sense of it. The congressman,” he says, echoing Sessions, “wants to cater to that.”

The rewards for Grayson have proven great, coming in the form of online donations from across the country — more than $600,000 has been raised on Democratic clearinghouse ActBlue, at an average donation of just $30. Grayson’s staff mines blog comments for ideas, and earlier this week, Daily Kos’ Markos Moulitsas named Grayson to its list of incumbents who would be targeted for community support. (Matt Stoller, one of the first and most influential progressive bloggers, serves as Grayson’s senior policy advisor.)

Part of what Grayson offers perpetually beleaguered Democrats is a take-no-prisoners attitude. When he caught flak for calling a female Federal Reserve advisor a “K Street whore,” he apologized — but only for the implied sexism of the comment. Democratic Hill aides marvel at the lack of deference he shows bankers and tycoons. After close examination of the Republican healthcare proposal last summer, he took to the floor to offer what became a famous assessment: The GOP plan amounts to “don’t get sick,” he said; and if you do, at least have the good sense to “die quickly.” Republicans flipped. Grayson refused to back down. His apology, this time, was delivered to the many Americans without health insurance caught up in the healthcare “holocaust in America.” For good measure, Grayson put up a website called Names of the Dead, and asked the public to send in stories of Americans who had needlessly suffered.

But Grayson’s headline-generating remarks obscure the fact that he does his homework. He actually did read the Republican healthcare plan. Another example: From his seat on the House science committee, Grayson recently grilled NASA’s administrator on the future of manned space flight. He looked, frankly, like a ’50s Miami gangster, black tie on white shirt. But Grayson knew the ins and outs of NASA’s space strategy, equipping him to mount a respectable challenge to the idea that the future of human space flight in the United States runs through private companies. In his attention to detail, love of a good government report, and bulldog tenacity, Grayson brings to mind the so-called mustache of justice, California Democratic Rep. Henry Waxman.

But unlike Waxman, Grayson doesn’t just want to figure out what went wrong, and maybe punish the bad guys. He also wants the public to understand where the country went astray. A backer of the idea that everyone should have an accessible Constitution handy at all times, he’s on a mission to teach you the whys and the hows along the way. When he took to the House floor one day last month, it looked like Grayson’s five children had attempted to replicate Picasso’s “Guernica” on his tie in crayola. He had a lesson to share, boiling down the collapse of Bear Stearns and subsequent central bank takeover of some of the company’s liabilities to a direct message to the American people. “I know what you’re thinking,” he said, clearly enjoying himself. “You’re thinking, ‘That’s funny, I don’t remember buying the Red Roof Inn.’” He went on, addressing the cameras. “The Federal Reserve, in its wisdom, has done it for you. Congratulations.”

The flaw in the conservative plan to caricature Alan Grayson as a crazy extremist — the left’s Michele Bachmann — is evident every time he asks a searing, informed question. If Grayson can survive November in Florida, he just might create a new model of how an aggressive Democrat can succeed in the YouTube age. And that’s when you’ll see Republicans really lose it.