Adam Willis is a freelance writer based in Washington, D.C.

During Mitch McConnell’s fifth reelection campaign, in 2014, he called into Kentucky Sports Radio unannounced. When Matt Jones, the show’s host and founder, welcomed the senator onto the program, it was hard to miss the hint of smug satisfaction in his rough-hewn mountain accent. Jones, who had been taunting McConnell on air for several weeks, went straight for a favorite jab, questioning the senator’s college basketball allegiances. McConnell has degrees from both the University of Kentucky and the University of Louisville and steadfastly refuses to pick a favorite between the two rival NCAA teams.

“Let me just say something,” McConnell interjected as Jones, a University of Kentucky fan, teed up his Kentucky-Louisville question. “It is OK—I know it’s probably not acceptable to you, as an Obama enthusiast—but it’s OK to be for both Louisville and Kentucky.”


“What does me being an Obama supporter have to do with Kentucky versus Louisville?” Jones laughed.

From there, the conversation shifted from basketball to the minimum wage, same-sex marriage and global warming—13 minutes of tense radio that might provide a preview of what the Senate majority leader is in for in his 2020 reelection race. Jones, the unabashedly liberal voice of the most popular radio show in the state, says he plans to oppose McConnell in Kentucky’s next election cycle if the senator chooses to run for another term. And some political observers say he might actually have a shot at ousting one of the most powerful figures in the Republican Party.

Jones has made McConnell a frequent target on his show in recent years, using the senator’s equivocation between the state’s two rival basketball programs as a proxy attack on his character. In Kentucky, where basketball reverence verges on the religious, anyone who claims dual loyalty is seen either as a liar or severely out of touch. To Jones, McConnell is both—in politics as well as sports. He calls out the Senate majority leader’s faux advocacy for Kentucky coal country, his “morally repugnant” tax bill and his allegiance to wealthy elites. Kentucky is a state of outsiders, Jones likes to point out—working-class people who have, for more than 30 years, been represented by Washington’s consummate insider. (McConnell’s office didn’t respond to multiple requests for comment.)

“What has Mitch McConnell done to help Kentucky?” Jones asks me in a phone call. “Mitch McConnell has been a master—a master,” he says, “at helping wealthy business interests get wealthier. If there is a rich guy Hall of Fame, he should be in it.”

Jones’ criticism is the sort of anti-establishment cri de coeur that tends to be more common on the Bannonite right. But Jones is a liberal populist—an outspoken champion of worker’s rights, a pro-choice, pro-gay marriage, pro-wrestling NASCAR enthusiast—looking to recapture the Trump vote from Republicans in a state the president won by nearly 30 points in 2016. Jones does have one big thing going for him—sky-high name recognition, thanks to his radio show, one of the most popular local sports shows in the country. Democratic insiders in Kentucky believe he might be uniquely qualified to take on McConnell.

Jones, who hardly lacks for self-confidence, agrees. “If it’s Mitch McConnell, I can win. And no other Republican will, and I don’t think any other Democrat can. But I can,” says Jones, 39, while slouched in a booth at a wings restaurant in Lexington, wearing a faded Cincinnati Reds sweatshirt and khakis. With a short, uneven haircut and a closet of University of Kentucky technical polos and visors, he looks like he would fit more comfortably into a fraternity house than the Senate chamber.

“I’m not a politician. I’m an ideologue,” says Jones, a smile peaking at the corner of his mouth, “and I think we’re in a time when ideologues win.”



***

The motivating force behind Jones’ political aspirations is an unflagging loyalty to his Eastern Kentucky home. He hails from Middlesboro, a mountain town in the heart of Appalachian coal country whose chief industry is manufacturing sewer covers. Jones grew up with his single mother, a Republican Commonwealth attorney for the surrounding county and one of the first women elected prosecutor in the state.

Jones earned full scholarships to Transylvania University and Duke Law School, where he graduated second in his class. But he forswore a legal career to start a sports blog in 2005. In 2011, he launched his radio show. KSR has since ballooned into the most popular show in nearly every district of the state, including the hostile precincts of Louisville. The accompanying sports blog, which looks like something out of the internet’s Neolithic era, is rumored to draw more daily readers than the Louisville Courier-Journal and the Lexington Herald-Leader.

Listener phone calls drive much of the conversation on KSR, which can veer from deep dives into UK basketball recruiting to debates over inane hypotheticals like, could so-and-so change a tire? (University of Kentucky men’s basketball coach John Calipari, yes; former Louisville head coach Rick Pitino, who was unceremoniously fired in October after a long, scandal-ridden tenure, no; Hillary Clinton, no; Mitch McConnell, a surprising yes). Jones brings a by-the-fans, for-the-fans philosophy to his media empire, aiming to mirror the conversation an average Kentucky fan might have in a bar on game day. Jones often complains that the Kentucky athletic department has forgotten “the common fan.” During a rant on a KSR broadcast in November, he joked about delivering his “State of the Average UK Fan Union.” He criticizes the university for hiking ticket prices, catering stadium renovations toward wealthy ticket holders, sticking with a checkerboard uniform pattern that is widely loathed by the Kentucky fan base, and frequently argues that “the fan experience for the Average Joe fan has gotten worse in the last five years.”

In recent years, that populist undercurrent has taken on an increasingly political tone. KSR has served as a forum for gubernatorial debates and exacting interviews with Kentucky politicians from both parties, and the show has gone on tour to broadcast from the White House and the Republican and Democratic National Conventions. In 2016, after Kentucky Senator Rand Paul wouldn’t come on the show, Jones and his co-hosts badgered the senator’s office with on-air phone calls asking for an interview. To a vocal minority of Matt Jones fans, the politicization of his platform is insufferable. But for much of his almost uniformly conservative fan base, Jones’ commentary offers a chance to hear a different perspective from a voice that they trust.

In 2015, Jones launched a nightly TV show in Lexington, “Hey Kentucky!” that has spread his brand to an even wider audience and allowed him to expand beyond the shackles of “stick to sports” in a way KSR never could. The show features a rotating cast of Kentucky politicos, many of them progressives, and nightly political analysis by Jones, often in the form of a methodical dismantling of the latest policy proposal by Republican Governor Matt Bevin.

“Hey Kentucky!” firmly established Jones as one of Kentucky’s preeminent political voices. Over the past two years, Jones has moderated gubernatorial debates, emceed Fancy Farm, Kentucky’s annual statewide political picnic, and launched the New Kentucky Project, a grass-roots organization aimed at recruiting young, ambitious political outsiders to recast the progressive movement across the state.

Defining Jones’ political identity is a slippery task—even for those in Kentucky who listen to him every day. When pressed, he identifies as a “Southern populist progressive,” wary of using the term “liberal” in his home state. He is a proponent of Obamacare and marijuana legalization, generally an advocate of free trade and lowering the corporate tax, bullish on union rights and a vocal opponent of corporate welfare. These stances almost universally find root not in party allegiance but in the effect on Kentucky’s working class, a mooring so deep that Jones says he would vote against his personal beliefs in the Senate—on coal, for instance—if he felt it was in the best interest of his constituents.

Jones talks about running for office often, both on and off the air. In 2015, he was recruited by national Democrats to oppose Republican Andy Barr in Kentucky’s 6th Congressional District, but after a political boot camp in Washington, he came away disillusioned with the Democratic Party. He recalls one prominent congresswoman advising the room of recruits that their stances on issues were not important, that raising money was all that mattered. “And that was one of the most depressing things I’d ever heard,” says Jones. He opted not to run that year, and when he made his decision the National Republican Congressional Committee released a statement celebrating the loss of the Democrats’ “last, best, and only” hope in the Kentucky 6th.

But now that he has a chance to put McConnell out of a job—the 76-year-old senator is reportedly planning to seek reelection in 2020—Jones is ready to give politics another shot. “I want that battle,” Jones tells me. He gets starry-eyed talking about it: “The idea that a dorky kid from Middlesboro, who lived with his mom, could take down the most powerful politician this state has seen since Henry Clay—how could you not do that?”

Such eagerness to face the Senate majority leader—one of the most powerful figures in U.S. politics—might sound like a death wish. McConnell is known as a ruthless campaigner who, if he does indeed choose to run, will bring enormous sums of money and decades of experience to any race. And there’s no love lost between the McConnell camp and Jones. Scott Jennings, a former adviser to McConnell, warns that Jones should be ready to answer for anything he has ever said on the air. “There’s an old adage in the McConnell world,” says Jennings, “‘if you throw a pebble at me, we’ll throw a boulder back at you.’ And Matt Jones has built up a whole quarry full of boulders.”

Josh Holmes, McConnell’s former chief of staff and campaign manager, says he thinks Jones has “mistaken the cheers for Big Blue Nation as cheers for Matt Jones.” Holmes is convinced the radio host’s campaign talk is strictly a “vanity project,” but says if Jones does want to venture a campaign in 2020 then, “absolutely, it would be my pleasure to help introduce him to the worst mistake he’s ever made.”

But McConnell is also facing some of the lowest in-state approval ratings of his career. One Public Policy Polling survey in August found just 18 percent of Kentucky respondents approved of the job McConnell was doing, while 74 disapproved. A Morning Consult poll in October found 33 percent of those surveyed approved and 55 percent disapproved—making McConnell the least popular senator in the country. As Jonathan Miller, a former Kentucky state treasurer and former chair of Kentucky’s Democratic Party, says, Kentucky has a working class, anti-establishment voter base, “and there’s nobody that symbolizes the insider establishment more than Mitch McConnell.”

And appealing to the working class happens to be where Jones excels. As a radio host, Jones has made a living taking aim at the people that he sees as Kentucky’s bullies, from Pitino to Bevin. “This is a guy who lives to annoy elites, This is a guy who lives to offend the haughty,” says Adam Edelen, Kentucky’s former state auditor and Jones’ New Kentucky Project co-founder. Jones says McConnell is the biggest bully of all, one who he alone has the platform, the policy expertise and the brazen confidence to take down.

For Jones to win a Senate election in Kentucky as a progressive Democrat—let alone to win it against the most consistent force in Kentucky politics over the past 30 years—would be historic. The state has never elected a supporter of abortion rights senator, and Jones would be by far the most left-wing candidate McConnell has faced. All of this as the state turns redder by the year.

Still, there is reason to think a populist Democrat could win in Kentucky. The state has a long tradition of favoring anti-establishment candidates, including Rand Paul, Matt Bevin and Donald Trump, in recent years. And with the rise of Trump, the dissonance between McConnell’s brand of economic conservatism and Kentucky’s blue-collar workforce has never been louder, a tension that could make for particular upheaval in Jones’ Appalachian home, a region that was solid blue not so long ago and the one where Jones finds his most fervent fans.

“In a political world where the candidates seem to be really scripted, really elite and really disconnected from the lives of the people they want to serve, I think Matt is the opposite of all those things,” says Edelen. While Edelen acknowledges the difficulties of winning a statewide election as a Democrat in Kentucky, he says that with Jones, “the calculus changes”—that Jones forces Kentuckians to rethink party allegiances.

Republicans aren’t discounting him either. “I think the question we will all have when [Jones] appears on the ballot is, is he bigger than politics?” says Trey Grayson, Kentucky’s former secretary of state and a longtime McConnell ally. Grayson also calls Jones a friend and considers him a legitimate candidate for the Senate, though he says he doubts Jones’ celebrity will be enough to overcome a Democratic Party affiliation and persuade Kentuckians to vote against ingrained values.

Miller, a self-described establishment Democrat, has been encouraging Jones to run for office for years. The former state Democratic Party chair has a history of backing outsider candidates (in 2014, he nearly succeeded in recruiting Ashley Judd into the Senate race) and believes Jones could be the agitator his party needs. While McConnell has been able to overcome his low approval ratings by attaching his Democratic opponents to the reputation of their party, Miller believes that Jones, as an outsider, would not come with the taint that the Democratic Party holds in Kentucky. “If you’re going to beat McConnell, you’re not going to beat him liberal versus conservative, Democrat versus Republican,” says Miller. “Those races, McConnell wins.” But tilt the race on its axis, make it insider versus outsider, he argues, and Jones could redraw partisan lines across the state.

Other Kentucky Democrats are more skeptical. Phillip Thompson, who served as the deputy campaign manager to McConnell’s challenger Alison Lundergan Grimes in 2014, dismisses Jones as “just noise.” He says that many in the Democratic establishment don’t take Jones seriously: “Until you actually have this experience, and get in there and run for something—city council, dog catcher, or something—I don’t think you really know what you’re talking about.”

Some pushback from Jones’ own side is not surprising. In addition to goading McConnell and Bevin, he has rustled plenty of feathers in his state’s Democratic Party, an institution he is quick to label a “disaster.” In 2016, as the Democratic banquet speaker on the night before Fancy Farm, Jones hammered his audience for abandoning its working-class base, retreating to liberal outposts in Lexington and Louisville, and compromising core principles to win conservative votes.

“We are on the right side of history on all of these issues,” he said, “but it’s not gonna matter in this state if we don’t get our act together.” He rounded out his speech by sounding alarm bells for the party, “In my opinion, we’ve got three to five years to make a move” or “not just the progressive movement, but the moderate movement in this state is done.”

***

Jones savors the outspoken outsider’s narrative. It was after growing frustration with Kentucky Democrats and a disastrous 2015 election cycle for the party that he teamed up with Edelen to found the New Kentucky Project. That year, an insurgent Republican Party pulled off a slew of upsets in statewide races, including a runaway victory in the governor’s race by the outsider businessman Bevin, a result that Jones says should have warned the country about Trump’s impending election. Jones reached out to Edelen after the Democratic state auditor suffered his own surprising defeat, and the pair got to work on a long-term project to replace a broken party in Kentucky.

The New Kentucky Project aims to recruit outsiders to run for local government and, hopefully, continue up the ladder to higher offices across the state. With chapters in all 120 Kentucky counties, Jones and Edelen have been on the speech circuit promoting the project. After one speech at a labor lunch in a Louisville hotel in October, burly union leaders with Civil War era facial hair approached Jones for selfies. “Matt is after the truth,” one of them, a leader in the Eastern Kentucky plumbers union, said, “and that is a rare thing these days.”

Jones hopes the New Kentucky Project can act as a unifier amid Kentucky partisanship. The group is organized around four pillars—education, health care, workers’ rights and equality—issues on which Jones believes most Kentuckians, regardless of party affiliation, can find common ground. It’s an optimism that stems from what he identifies as his core belief, “that 75 percent of Americans agree on 75 percent of the issues, and that politics exists to divide the rest, to use the 25 percent they disagree with to divide the people completely.”

Jones therefore espouses a doctrine of empathy that you won’t hear from many liberals today. “I wish the people that I love didn’t like Donald Trump,” he says, “but I understand why they do.” Jones says he is “not someone who will do the game that people do now, on both sides, of ‘this is a good person and that is a bad person.’” He frequently states that he would prefer to talk about issues rather than people, good and bad characteristics instead of good and bad folks. He points to Kim Davis, the county clerk in Kentucky who drew national headlines in 2015 for her refusal to approve same-sex marriage proposals, as an example. Jones says he understands the hearts of evangelical conservatives like Davis far better than those who condemn them: “I know people like Kim Davis, and you don’t.”

It is this sense of mutual respect that Jones feels he has with Kentuckians, more than anything else, that he believes sets him apart from others who have tried and failed to unseat McConnell. Jones claims to talk to more conservatives on a daily basis than any progressive in the country—he estimates that 80 percent of his listeners are Trump voters.

If he does pull off an upset over McConnell, “it will not be because of basketball, it will be because people think they know me,” Jones says. When asked if he still feels a connection to his hometown of Middlesboro, the seat of a county that voted nearly 80 percent for Trump in 2016, Jones brings up a celebration that the town put on last summer called “Matt Jones Day.” At the event, the radio host’s hometown presented him with what is now his most prized possession. The gift, a massive, cast-iron sewer cover, lies flat and inauspicious on the carpet beneath the television in his apartment.

MATT JONES, it reads, in big, embossed letters, THE PRIDE OF MIDDLESBORO.