Alison Grimes will challenge Republican Mitch McConnell in the Kentucky Senate race this fall.    (Photo: Ryan Pfluger )

Alison Grimes walks into the room and conversation stops. It’s a friendly crowd—a little more than a dozen regular folks who have been assembled by Grimes’s U.S. Senate campaign staff for a “roundtable” on higher-education costs in the Danville, Kentucky, library. But Grimes is a star and nearly five-foot-ten in the crocodile-print high heels she’s wearing this morning. The group looks a bit intimidated. The candidate hugs her way around the room, lowering the tension before taking a seat at the head of the conference table and asking for introductions.

Clay Williams, 16, still seems a bit shaky when it’s his turn. So Grimes, 35, starts what will become a running joke, coming across as teasing Aunt Alison: “A high-school junior?” she says. “Are you driving yet? Oh, wooo! They took my keys a long time ago!” This opens the door for Williams to volunteer something pretty brave for a teenage boy in a roomful of adults. “My dad lost his job,” he says quietly. “My parents have no idea how they’re going to pay for college now.”

This event was staged to generate publicity for Grimes’s proposal to lower interest rates on student loans, and she fluently discusses the wonky policy details. But then the discussion expands into a sometimes wrenching airing of the stresses of middle-class life. Jennifer Kirchner, 35, is pregnant with her third child; she’s a local tourism official, her husband is a professor at Centre College. “Our student-loan payments are now more than our mortgage,” Kirchner says. “There are days where we’re up at night thinking, Wow, how are we gonna make this work tomorrow?”

Grimes nods empathetically, then throws an elbow at her campaign opponent, Republican Mitch McConnell, who led a filibuster to kill a bill aimed at lowering student-debt payments. “What did you think of Senator McConnell’s actions over the past month regarding refinancing?” she asks.

“I’m angry, I’m really angry,” Kirchner says. “I haven’t messed up. I’m doing what I’m supposed to do, and I just need a little bit of help.”

Grimes seems genuinely moved. Ten minutes after the discussion, when she sits down with me, she’s rapidly shaping these stories into a cudgel. “We had the opportunity today to hear from the people who give me the fight each and every day to stand up to the millions of dollars in negative, nasty attack ads that Mitch ­McConnell has made the central tenet of his campaign,” Grimes says, her words a fusillade, her blue-gray eyes cold. “When Mitch ­McConnell went to the United States Senate—1984—big hair was in, cutoff sweatshirts were all the rage for women, Wham! was the band of the time. Those things aren’t coming back in 2015, and I don’t think Mitch ­McConnell will either.”

The cadences are straight out of the Ann Richards school of sound-bite delivery. But Grimes doesn’t yet have the late former Texas governor’s deft touch. She swings between jackhammer relentless and maddeningly cautious. Which is typical of the many tricky straddles that Democratic Senate candidates are attempting all over the country this election season: distancing themselves from President Barack Obama while spending the millions of campaign dollars he raises; tapping into populist anger over the sluggish economy while avoiding the taint of liberal coastal elitism. In more than an hour of talking about student debt, for instance, Grimes doesn’t speak Obama’s name, let alone mention how the president has lowered college costs. The game is playing out with variations and eccentricities peculiar to each state and campaign—and nowhere with as much bile, and money, as in Kentucky.

The Homegrown Challenger

Alison Lundergan Grimes is in some respects a female JFK figure: young, great-looking, charismatic, and the scion of a large, politically marinated Roman Catholic family. She even has the hard-driving father with invaluable grassroots connections—and baggage that could turn out to be a liability.

Jerry Lundergan, 67, is the first to applaud and the loudest to laugh during his daughter’s events—“an in-your-face good ol’ boy,” in the words of a Democratic colleague. As a boy, Jerry pitched in with his siblings to help their parents sell lemonade and fried ham sandwiches on Kentucky’s carnival-and-fair circuit. The 18-year-old Lundergan took over when his dad died suddenly; today he is a millionaire owner of thriving catering and emergency-services companies. Lundergan’s businesses helped revive his small hometown, Maysville, and the catering company has served a papal visit and Chelsea Clinton’s wedding.

After winning a state House seat in 1979, he rose to become chairman of Kentucky’s Democratic Party. But Lundergan’s career as an elected official was bruising—he clashed repeatedly with Steve Beshear, Kentucky’s current governor—and its end was bitter: In 1989, Lundergan was convicted on ethics charges after a lucrative state contract had been awarded to his catering company. (The conviction was later overturned on appeal.)

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