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American Derby

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Grimes (with ponytail) at Bill Clinton’s 1993 inauguration.   

But he’s also made some missteps. In 2009, McConnell forced fellow Republican senator Jim Bunning into retirement, in favor of a McConnell protégé named Trey Grayson. The timing was terrible: McConnell missed the stirrings of Kentucky’s tea-party movement, which got behind Rand Paul, who easily dispatched Grayson. This spring, in the Republican primary, McConnell faced his own tea-party challenger, businessman Matt Bevin. McConnell, nimbly learning from his mistake, hired Paul’s campaign manager, Jesse Benton, and managed to make Bevin look foolish for appearing at a pro-cockfighting rally. McConnell beat him by 25 points.

McConnell’s appearance at the Right to Life convention was as much tactical as philosophical. McConnell has been consistently anti-abortion for years, but not stridently so. Now, in his race against Grimes, he’ll need to turn out the state’s socially conservative Christian voters. (Grimes is pro-choice.)

Yet in July McConnell seemed to acknowledge just how tight this race is, by proclaiming his support for a Republican bill affirming that “employers cannot prohibit a woman from accessing contraception.” Legally, the idea is meaningless: It wouldn’t alter the Supreme Court’s Hobby Lobby decision granting private companies a religious exception to insurance coverage of birth control. But politically it was a small sign that moderate women are a key swing vote in Kentucky—and that McConnell realizes he’s vulnerable in November.

Still, Kentucky’s professional Democratic class remains pessimistic. Mostly because it has learned to fear McConnell. “That comes from him having had a hand in naming pretty much every state judge and prosecutor in the past 30 years,” a Kentucky political operative says. In campaigns, McConnell is ruthless. “Mitch doesn’t just run against you,” says one Democrat. “He’s a genius at finding ways to make you unacceptable.”

Last week McConnell was handed a new opening. Politico reported that Jerry Lundergan’s companies have provided his daughter’s campaign with a bus and party facilities at discount prices. The campaign says it is paying market rates, but ­McConnell wasted no time in using the story to flay Grimes as an untrustworthy rule breaker. “Alison’s doing fine,” a former Kentucky elected official says, “but nobody really knows who she is yet. And Mitch is just getting warmed up hammering her as a tool of Obama.”

The Master of Attack

Scott Jennings is charming, he’s fun, he’s dressed prosperous-dad-casual in an Owensboro Country Club polo shirt and khakis. He’s also lethal.

Big campaigns these days are fought as much by proxies as by the candidates, especially after the Supreme Court decisions in the Citizens United and McCutcheon cases tore down limits on corporate spending and campaign finance. Kentucky is this year’s shining beneficiary, or victim, of that flood of money, with tens of millions flowing into the race on both sides. The actual spending of the money, though, is the province of super-PACs with delightfully Orwellian names like Kentuckians for Strong Leadership.

Jennings is KSL’s media consultant. Many of the ads bombarding Grimes are dreamed up here, in his nondescript Louis­ville office upstairs from a chiropractor and behind a Panera Bread. (The super-PAC is carefully legally separate from the ­McConnell campaign.) Jennings honed his craft working for Karl Rove at the Bush White House. Ask him about Grimes and he is exuberantly, precisely pugnacious.

“This is a candidate who, once asked about Obamacare, said that it was a job creator,” Jennings says. “I mean, I don’t think most Kentuckians see it that way. Especially when hospitals in Ashland, Glasgow, and Louisville and Lexington are laying people off. She endorsed Obama in ’12 when everyone else in the state was running in the other direction. I love that setup. I love the equation in a state where Mitt Romney won 116 counties.”

Kentucky’s northern suburbs, outside Cincinnati, are one key to the tight contest. The area is culturally conservative, thoroughly Republican, and traditionally a McConnell bastion. Will they stay home on Election Day, or can they be motivated to come out and vote against Grimes? Jennings jumps from his chair and walks over to a wall map, pointing confidently. “If Alison Grimes is pinning her hopes on the Republicans of Boone County bolstering Barack Obama, great,” he says. “I’m super-glad that’s her strategy. Super-glad.”

“If she wants to fund-raise with Michelle Obama in New York City, great,” he says. “It further confirms the very simple box in which I think this campaign is gonna be fought. You have another vote for the Obama-Reid national Democrat agenda. Or you have Mitch McConnell. A proven conservative, a consistent fighter for Kentucky, versus somebody who’s gonna fall in line with the Obama-Reid plan. We’ve got plenty of money, time, and ability to tell that story.”


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