Mitch McConnell is one of the wiliest, savviest politicians in America, nearly anyone will tell you. Thirty years ago, the Senate Minority Leader helped rejuvenate the Republican Party in Kentucky and though it still has more registered Democrats than Republicans, his dominance as the state's longest serving senator has been complete.
But now, running for his sixth term, McConnell faces war on two fronts at a time when Washington politicians, particularly Republicans, are viewed in a record unfavorable light by the American public.
In one corner, McConnell is competing with a somewhat formidable primary opponent in businessman Matt Bevin, who recently won the nod from national conservative groups like the Madison Project and the Senate Conservatives Fund. The groups are taste-testers for the tea party and can provide much-needed outside funding for Bevin, who has struggled to fundraise against McConnell, while at the same time he has dumped at least $600,000 of his own money into his campaign so far.
"Obviously enough people nationwide on the right are mobilizing against McConnell that it's starting to look as though [Bevin's] going to be able to get his message out there and that's huge," says Stephen Voss, a political science professor at the University of Kentucky. "But insofar as he forces McConnell to shore up his right flank, that certainly hinders the Senate Minority Leader as he goes into the general election against a Democratic candidate who is polling fairly well."
That candidate is Alison Lundergan Grimes, who poses the largest threat to McConnell's re-election, from the opposite corner of Bevin. Grimes' father was a former Kentucky Democratic Party chairman and she recently won a statewide election to become the Kentucky secretary of state.
Grimes has rocketed to the top of the national Democratic stage, as the candidate who could potentially knock off the top Senate Republican. Top Democratic donors nationwide are flocking to give, including some high profile names from Hollywood. According to The Associated Press, DreamWorks Animation CEO Jeffrey Katzenberg hosted a September fundraiser for Grimes, garnering contributions from the likes of Leonardo DiCaprio, Ben Affleck, Nicholas Cage, Ted Danson and Ben Stiller. The Hollywood connection is ironic, considering Grimes jumped into the race only after actress Ashley Judd took a pass on running.
"I know she's going to get a lot of national Democratic money, but that to me is almost as much a liability in Kentucky as an asset because when you get outside the urban areas, they don't take to the Hollywood stuff," says John David Dyche, a GOP analyst and McConnell biographer.
Grimes also has a tough row to hoe in Kentucky when it comes to differentiating herself from President Barack Obama and his policies that she would presumably be pressured to support as a Democratic senator. The president earned just 38 percent of the vote in Kentucky in the 2012 presidential election and it made headlines earlier in the year when 42 percent of voters in the state's Democratic primary said they were "uncommitted" rather than casting a vote for the unopposed Obama.
"The stickiest issue will be with the president and she has distanced herself with him," says Terry McBrayer, a lawyer and former Kentucky Democratic Party chairman.
Grimes has campaigned as a pro-coal Democrat and said the penalty for having health insurance under Obama's Affordable Care Act should be delayed until the online marketplace's website issues have been resolved. But political observers say McConnell will pound her on de facto allegiance to Obama.
"She's going to have two really big problems – the Obama administration policies on coal and Obamacare," says Dyche. "And in Kentucky when you take coal and Obamacare and Obama's unpopularity and then throw in the gun issue, I just don't see it happening."
Grimes has also been hit by Republicans for being anti-coal because Senate Majority Leader Harry Reid, an outspoken opponent of coal, recently hosted a fundraiser for her. And she's received campaign donations from clean energy groups, providing more fodder to conservatives hoping to use it as a wedge issue.