With his retinue of notorious celebrity friends, including former pimp Heidi Fleiss and boxer/convicted rapist Mike Tyson, and his previous history running for office as a Republican, billionaire Jeff Greene is not the kind of candidate the Democratic machine would necessarily put up for U.S. Senate.

Many Republican officials see multi-millionaire businessman Rick Scott’s controversial past running a chain of hospitals that ultimately admitted to massive Medicare and Medicaid fraud as insurmountable baggage in the general election for governor.

Yet both candidates have made inroads in their respective primary battles, and their success puts the state parties they hope to represent in a predicament: stay neutral in the intra-party races or actively offer endorsements.

The Democrats are straightforward despite the potential consequences. “The Florida Democratic Party is supporting Kendrick Meek,” the party’s communication director Eric Jotkoff says. “Along with Democrats across Florida, we stand with Kendrick Meek because he is the leader we need to fight for us and bring jobs to Florida.”

Florida Democrats have cover, sort of, in that the Democratic National Committee has officially endorsed Meek — DNC chairman Tim Kaine told the St. Petersburg Times that Meek was the party’s “nominee.” The state party can claim it is just following directives from its national overseers.

But with Greene spending more than $5 million on the race so far, and a June poll showing him pulling even with Meek, it begs the question: what if Greene wins the nomination? Would the party give him money, staff, and infrastructure? Would they put the whole weight of their organization behind Greene? It’s clearly a dilemma the party does not want to find itself in. Jotkoff is unwilling to ponder that possibility publicly. “We’re confident Kendrick Meek will be the next U.S. senator from Florida,” he repeats.

Meanwhile, the Republican Party of Florida is officially not taking sides in the primary race for governor between state Attorney General Bill McCollum and Scott. “The party is neutral,” declares RPOF spokeswoman Katie Gordon Betta.

The RPOF is still smarting from the miscalculation its former chairman Jim Greer made by openly backing Gov. Charlie Crist’s candidacy for U.S. Senate, even as upstart former house speaker Marco Rubio developed a following among grassroots conservatives. Greer’s ham-handed tactics, along with his profligate spending on the party’s dime, turned many against RPOF leadership, forced Greer’s ouster, and helped make Crist’s run as a Republican untenable. Crist has since left the party and is running as an independent. Greer was arrested and faces charges of stealing party funds.

In the wake of the scandal, Republican leadership is striving to be even-handed in the contest. Yet, when the RPOF’s new chairman, state Sen. John Thrasher, publicly reprimanded Scott last week, the claims for neutrality seemed thin.

Thrasher castigated Scott for his campaign ads claiming that McCollum and others in the Republican leadership knew more about Greer’s misdeeds before his arrest than they let on. “Mr. Scott’s repeated attacks on Attorney General McCollum, [state Rep.] Dean Cannon, and [state Sen.] Mike Haridopolos are not based in truth and come straight from Jim Greer’s talking points,” Thrasher wrote on July 6. “I’m hopeful Rick Scott will begin to lay out a positive message for why he is running for the Republican nomination to be our next [g]overnor, instead of continuing to release false statements regarding fellow Republicans.”

Scott’s ads were damaging to the party and its candidates, Gordon Betta says, and Thrasher’s comments were intended to defend all Republicans. People may further be confused about the party’s neutrality, she continues, because the RPOF worked closely with McCollum’s campaign in the months before Scott entered the race in April. The RPOF had donated more than $1 million to McCollum’s war chest by then. Now she says, the party has backed off.

“There are a lot of resources out there that we have given to the Scott campaign,” Gordon-Betta says, including lists of Republican clubs in the state, district maps, voter registration lists. “He’s been offered the same resources Bill McCollum and any other statewide candidate has been offered.”

Still, the party’s website had a banner ad featuring McCollum Wednesday, ostensibly because he is the state’s attorney general. And a list of the party’s major players from Haridopolos to former Gov. Jeb Bush has endorsed McCollum. McCollum’s campaign headquarters and the RPOF even share the same address — 420 E. Jefferson St., Tallahassee.

All of which plays into Scott’s campaign. He actively courts tea party activists and other disaffected conservatives by proclaiming his outsider status, while derisively portraying McCollum as a career politician.

The great paradox of this campaign season is that Greene and Scott, outsiders by definition, are attempting to work within the party system, while one of Florida’s most established politicians, Charlie Crist, is forced to run without the aid of a major party.

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