Will This Bourbon-Loving Kentucky Conservative Usher in Prison Reform? - OZY | A Modern Media Company

Will This Bourbon-Loving Kentucky Conservative Usher in Prison Reform?

Will This Bourbon-Loving Kentucky Conservative Usher in Prison Reform?

By Nick Fouriezos


Because advocates like her make the Washington wheels go round.

By Nick Fouriezos

The black-heeled, red-dressed Kentuckian makes the trek from Union Station to Capitol Hill for her most important sit-down in three years of fighting for criminal justice reform. As director of the Justice Action Network, Holly Harris has helped funnel hundreds of thousands of dollars to advocacy groups on both the left and right of this mostly bipartisan issue. Now, the First Step Act — which could ease punishment for well-behaved prisoners, exempt some drug offenders from mandatory minimum sentencing laws and prohibit the shackling of incarcerated pregnant women — is closer than ever to becoming a reality. Harris is quickening her pace. 

While there are many working to help pass criminal justice reform, Harris and the Justice Action Network are seen as key to the First Step Act’s potential passage. “I don’t know if we would be where we are today without them,” says Sen. Mike Lee, a Utah Republican and major proponent of the bill. “For a long time, Democrats really were scared to be seen as soft on crime and weak on this issue,” says Jessica Jackson Sloan, a left-leaning human-rights attorney and co-founder of reform initiative #cut50. But she says the voices of Republicans like Harris have been a “turning point,” making the issue bipartisan rather than politically toxic. 

She has all the attributes of a Southern Belle packing heat.

David Safavian, of the American Conservative Union Foundation

It’s her roots that set Harris apart in this fight: The blonde University of Kentucky law grad is a veteran of Bluegrass State politics. And the bill has come down to a tug-of-war between her home state’s two GOP senators: Rand Paul, a fierce advocate who has barnstormed Kentucky and Washington with his wife, Kelley, on behalf of the bill, and Mitch McConnell, who is hesitant to allow a vote on a bill that could be perceived as soft on crime and reveal cracks in his Republican caucus. 

She knows that McConnell, who is up for re-election in Kentucky in 2020, is torn. “He has a role to play that is difficult. He has to balance the voices of those in his caucus and also the voices back at home. Ultimately, I think the latter will win out.”

This is why the 41-year-old single mother took the 6:18 a.m. flight from her home in Lexington, Kentucky, one morning last week, part of a commute to Washington now happening two to three times a week. From her office in the Hall of the States building, she convenes with some of her bipartisan staffers — one is a former intern for Democratic Sen. Cory Booker, another worked for the Barack Obama campaign in Waco, Texas. The West Wing and Gone With the Wind lover often talks of bourbon and horse racing and is deeply skeptical of the airplane stroopwafels (syrup waffle) her colleagues offer her. And through scrutinizing the word choices in press statements, tracking who is talking on which morning shows and debating the motives of various policymakers, they come up with a strategy to push the First Step Act through before the end of the year.


This may be the battle Harris was born for, having worked her way up from an entry-level attorney in the state law enforcement agency to chief of staff at the Kentucky Department of Agriculture. Her father was an itinerant suit-wearing orthodontist while she was growing up in Elizabethtown, but it was her conservative fundraiser mother who paved the way for her fixer status today. Cursed (or blessed) with “a serious lack of patience and a short temper,” as Harris puts it, she is also charming, joking about marrying her son off to the daughters of fellow criminal justice crusader David Safavian, of the American Conservative Union Foundation.

“She has all the attributes of a Southern Belle packing heat,” Safavian says, complimenting Harris’s communication skills in “a town where perception is often reality.” Those skills have helped her rise from the lowly task of handling prison transfers to working as the Kentucky Republican Party’s general counsel and finance chair — in a building named for McConnell. 

At the Kentucky Department of Agriculture, Harris helped convince McConnell to back legal hemp as a cannabis derivative with few psychoactive components but plenty of opportunities for profit. “Holy hell, Holly Harris knows her state better than anyone I’ve ever met,” says Jason Pye, vice president of legislative affairs for libertarian-leaning advocacy group Freedom Works. As for McConnell? “She knows the things to say to get his attention.”  

With President Donald Trump holding two major press events to support the First Step Act, and with perhaps 65 to 70 senators across both parties willing to back the bill in an increasingly split Washington, Harris can’t believe they have come this far. “It’s really the perfect storm. I keep thinking I’m going to get hit by a bus,” she laughs.

Still, there remain complex forces at play. Arkansas Republican Sen. Tom Cotton has repeatedly bashed the bill, saying it could let sexual deviants and violent criminals off early, despite safeguard provisions. And even in the face of a home-state charm offensive, McConnell remains hesitant. “The reason, if we don’t move forward, will be Mitch McConnell is worried it divides the Republican caucus and it gives the opportunity for a bipartisan win,” says Colorado Sen. Michael Bennet, a Democrat. 

“It will actually be tragic if this opportunity passes us by,” Harris reflects. But win or lose, she’ll be flying home tonight to tuck her 7-year-old into bed, a brief respite before she rejoins the whirl of Washington.

Read more: Meet Trump’s defender from the trenches of the D.C. swamp.

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