Illustration by Ryan Inzana.

The week after July 4, rare sightings of a strange creature from the East began to be reported across Kentucky. When he visits the state he’s represented in the Senate since 1985, Mitch McConnell, the jowly old swamp monster from Washington, D.C., doesn’t typically roam far from the tony Louisville neighborhood where he maintains a residence. As an elder Democrat told me last summer at Fancy Farm, the state’s annual political picnic, “If you see that buzzard popping up all around Kentucky all of a sudden, you can damn well be sure of one thing: He must be up for reelection.”

Sure enough, as he pursues his seventh term in the Senate, McConnell was popping up in all kinds of unlikely places during Congress’s traditional two-week July 4 recess. The Senate majority leader had left Washington amid howls of protest over his refusal to cancel the break; Democrats, as well, seemed to believe that passing another coronavirus relief package to deal with the pandemic and the economic meltdown ought to take precedence over vacationing or campaigning.

McConnell didn’t bat an eye. For him, there has never been any business more urgent than his next campaign. “He really exemplifies more than anyone else in Washington the permanent campaign mindset, where everything is about winning the next election and nothing else matters,” explains Alec MacGillis, the author of a biography of McConnell aptly titled The Cynic. “For McConnell, it’s not really about what he does while he’s in power to address problems or [pursue] his party’s policy goals, whatever they might be. It’s really only about setting himself up to win the next race.”

And so the millions of Americans desperately worried about evictions, school reopening plans, stimulus checks, unemployment benefits—not to mention life and death amid surging cases of Covid-19—would just have to cool their jets until McConnell returned on July 20. He had far more pressing matters to attend to in Morehead and Willisburg, Bardstown and Glasgow, Bowling Green and Henderson, Leitchfield and Covington, to name just a few of his stops. He wasn’t holding rallies in these places; he doesn’t do rallies, any more than he mixes and mingles with voters. This was a carefully scripted photo-op tour designed to highlight the senator’s caring, compassion, generosity, and statesmanlike leadership during the pandemic.

On Monday, July 6, for instance, you could find the Senate majority leader standing at a microphone at Bardstown’s Flaget Memorial Hospital, which received funding from the Cares Act passed in March. Virtually every stop on his recess itinerary was a hospital or health clinic that got funding—meaning that, everywhere he goes, he is sure to be praised and thanked before his carefully calibrated remarks, which urge Kentuckians to practice personal responsibility during the pandemic. “Everybody’s got a role to play to get through this,” McConnell solemnly intoned in the distinctive, deep-down drawl he acquired as a child in Alabama and Georgia. “Clearly, a lot of people thought when we started opening up the economy again, ‘Let the good times roll.’ And a lot of people went out, and we’ve seen the spiking of cases.” His face was a perfect rictus of disapproval. “Since we’re not gonna shut down the economy again, we’ve gotta figure out how to work through this, and the single best thing we can do is wear a mask.” He waved a light blue disposable model in the air for effect.

It’s much the same in town after town. The senator knows that his sermonettes on mask wearing will make perfect bits for the local 6 o’clock news or the next morning’s local paper, which will also surely mention how much money McConnell directed to the clinic or hospital to help it weather the crisis. While he’s traipsing around the state displaying his benevolence and his sober leadership, his campaign is reinforcing the message by airing a new ad called “Saved,” featuring a series of small-business owners thanking him for rescuing their livelihoods with the Paycheck Protection Program. This is vintage McConnell—every six years, anyway.

He knows that he needs to gin up all the positive spin he can between now and November. He has never been popular—and certainly not beloved—in Kentucky, even among Republicans. But ever since he became majority leader after his reelection in 2014, he’s consistently ranked as one of the most loathed members of Congress back home; in August 2017, McConnell’s approval rating in Kentucky was at an almost unthinkable 18 percent. His survival instinct told him in 2017 that his best bet for the next election was to hitch his wagon to Donald Trump, who carried Kentucky by 30 points in 2016, even though McConnell reportedly detests the president. So he became Trump’s unlikely but faithful lieutenant, delivering the few major policy triumphs the president can claim—all those conservative judges and all those tax cuts for the rich, most notably.

Clinging to Trump looked like a better strategy one year ago than it does today, of course. But despite Trump’s terrible and awful 2020, he’s still far more popular than the senator. And so, no matter what depths of insanity and depravity Trump may plumb between now and November, McConnell is stuck; he can’t afford to poke the bear, risk becoming a target of Trump’s wrath, and alienate the president’s fans in Kentucky. The careful and calculating McConnell has no choice but to clutch the coattails of the most undisciplined politician in American history.

Meanwhile, for the first time ever, the senator is experiencing another reality: He’s being beaten in fundraising and hit early on the airwaves by his Democratic opponent, Amy McGrath, while being attacked by a host of well-funded PACs and groups hell-bent on taking him down. McConnell had always wanted to be majority leader, but it sure is complicating things when it comes to winning again. “He’s never undergone this level of early and sustained attacks,” says Al Cross, the dean of Kentucky political journalists, who has covered McConnell for nearly three decades. “He’s never been under this level of intense scrutiny at the national level…. And because he has no reservoir of popularity or loyalty to draw on, he has to stick with Trump, come hell or high water.”

Even with so much stacked against him, however, you’d be hard-pressed to find a political observer who believes McConnell can lose. (Pollsters mostly rate the race as likely Republican.) That’s partly because the GOP wins almost everything in Kentucky these days and because Trump will almost surely carry the state again. It’s also because no one can really conceive of McConnell losing; deservedly or not, he’s widely considered the canniest, most ruthless, most strategically brilliant politician around—while this year’s opponent, despite her fundraising prowess, emerged from June’s Democratic primary looking fatally flawed and hopelessly overmatched.

Amy McGrath addresses supporters during a campaign stop at Woodland Park in Lexington in August.(Ryan C. Hermens / Lexington Herald-Leader via AP)

McGrath was supposed to sail smoothly to the Democratic nomination this June. She became a rising star in a flash in 2017, when her long-shot campaign for the House kicked off with one of the buzziest videos of the midterm elections, a slick biographical spot about how she became the first woman Marine to fly an F/A-18 in combat and how she’d returned to her native state with a “new mission” to “take on a Congress full of career politicians who treat the people of Kentucky like they’re disposable.” She fell just short of unseating Republican Andy Barr, a McConnell acolyte, after committing some rookie blunders that Republicans used to redefine the centrist Marine on a mission as a secret left-wing radical.

At a fundraiser in Massachusetts in 2018, McGrath was a little too eager to please her audience, claiming, “I am further left, I am more progressive, than anyone in the state of Kentucky.” And on a talk-radio show back home, she answered questions about abortion by robotically repeating her prepared talking point—“I don’t think the government should be involved in a woman’s right to choose what is happening to her body”—even after the host asked, “So you think a woman on the way to the hospital to give birth could decide to abort it instead?” By November, these audio clips had been aired so often on radio and TV in McGrath’s district that most voters probably could have repeated them verbatim. But she raised a ton of money from admirers around the country and shaved around 19 points off Barr’s previous margin of victory, and that was enough for Chuck Schumer, the Democratic Senate leader, to recruit her to try again in 2020, this time against McConnell.

By June 1, three weeks before this summer’s primary, McGrath had hauled in nearly $41 million, more than any other Senate candidate in the country. Which made it all the more shocking when she came within a whisker of losing the nomination to Charles Booker, a first-term state representative who entered the race late, in January, and started the final stretch with less than $300,000 to spend. If McGrath would have lost with all that money and all her other advantages, “it would have been one of the biggest pratfalls in American political history,” Cross says.

McGrath had nearly sunk her chances long before—as soon as she announced her candidacy in July 2019, in fact. After promoting her bid on Morning Joe, she “promptly fired a Sidewinder missile into her own foot,” as Courier-Journal columnist Joseph Gerth put it, by criticizing McConnell for not being helpful enough in turning Trump’s “good ideas” into policy. “The things that Kentuckians voted for Trump for are not being done,” she said. “He’s not able to get it done because of Senator McConnell.” In a later interview, she was asked whether she considered herself a “pro-Trump Democrat” and demurred rather than denying it. “This isn’t about being pro-Trump or anti-Trump,” she said. “You can’t put me in some partisan box. And this is the major difference between me and someone like Senator McConnell. If it’s a good idea, I’m for it. It doesn’t matter if you wear a red jersey or a blue jersey.”

If that wasn’t enough to make progressives cringe, there was worse to come when the interviewers turned to the controversial Supreme Court confirmation of Brett Kavanaugh. How would she have voted? McGrath, who had tweeted her opposition to Kavanaugh in July, hemmed, hawed, then finally answered, “Yeah, I probably would have voted for him.”

Cue Twitter eruption. By 7:30 pm, McGrath had hastily reversed course, tweeting that “upon further reflection and further understanding of his record, I would have voted no.” For some on the left, she was now permanently branded as a pro-Trump Democrat so eager to pander to the right that she had become pro-Kavanaugh. To conservatives, she looked like a flip-flopper who’d caved easily to pressure from the 
social-justice warriors. (“Take your third position on this later,” one Republican Senate aide chirped. “The night is still young.”) To others, she looked just plain inept, especially for a candidate who wanted to knock off McConnell.

Forgotten amid the chorus of hoots and jeers was the news that should have emerged from McGrath’s moment in the spotlight as McConnell’s new challenger: In spite of everything, she’d raised a record $2.5 million in the first 24 hours after her launch video dropped. National donors never stopped ponying up for McGrath, especially as no viable Democratic challengers emerged until Booker stepped forward. Her campaign’s anti-McConnell messaging was often sharp and timely on social media and in her daily e-mail blasts. She ran a general-election campaign from the beginning, which seemed like a safe thing to do. By April, Booker had climbed into second place, but with only 11 percent.

Booker, who likes to note that he lives in one of the poorest zip codes in Kentucky, the predominantly African American West End of Louisville, ran on a bold and clear set of progressive ideas (universal basic income, a Green New Deal, and systemic criminal justice reform). He wowed Democrats from the start with his “hood to the holler” message of bringing together working Kentuckians across racial and geographic divides—or at least he wowed the Democrats he could reach, without much money to advertise and with the pandemic preventing him from whipping up support in person across the state. Liberal donors nationally had long assumed that McGrath was the anti-McConnell candidate for 2020, just as Schumer intended, and Booker garnered little attention outside Kentucky. Until everything changed.

On May 28—three days after the killing of George Floyd by Minneapolis police ignited protests across the country and 26 days before the primary—audio of the fatal police shooting in Louisville of medical worker Breonna Taylor two months earlier became public. The West End rose up immediately, followed by protests across the state, and Booker quickly emerged as a leading and powerfully resonant voice of both calm and defiance. On June 1 he showed up for the only Democratic debate of the primary, fresh from the streets. His campaign-long message was made for the moment; McGrath was not ready for it. When a moderator asked whether she’d been “on the ground with the protesters,” she admitted she hadn’t. Why? “I’ve been with my family,” she said, “and I’ve had some family, um, things going on.”

Booker, with donations finally pouring in, turned McGrath’s deer-in-the-headlights moment into a devastating ad, juxtaposing it with footage of him speaking into a bullhorn as a “good troublemaker.” He soon picked up endorsements from the state’s major newspapers and from national politicians, including Senators Elizabeth Warren and Bernie Sanders and Representative Alexandria Ocasio-Cortez; he also led rallies around the state and soared in the polls. In all his time covering Kentucky politics, Cross had never seen the likes of it. “He just caught fire—caught a wave like no candidate I’ve ever seen,” Cross says.

Turnout in the Democratic primary was far higher than anticipated, no doubt because of the first-time voters Booker had inspired. On election night he was in the lead, but since most ballots were mailed in, it was a week before the final tally. McGrath was probably saved, barely, by the ballots that were sent in before Booker’s surge. “If the primary had been postponed or all the ballots cast in the last week,” Cross says, “he would have won.”

Mitch McConnell in 1997. He has served in the Senate for the Republican Party since 1985. (Maureen Keating / CQ Roll Call via AP)

McConnell has richly earned his reputation as a master of the art of political destruction, ever since his first local race in 1977. He learned it in part out of necessity. Blessed with almost none of the assets that typically make for a winning politician—charisma, eloquence, ideological passion, wealth—he decided early on that his surest path to victory was to make his opponents even more disliked than he is. For Team Mitch, nothing is off-limits. McConnell has used marital strife, allegedly corrupt family members, inherited wealth, prescription drug habits, and membership in a fox-hunting club to paint his opponents as corrupt, darkly menacing, out of control, or elitist and alien.

“McConnell’s campaign style is personal destruction,” writes Matt Jones, the founder and much-loved host of Kentucky Sports Radio, in his book Mitch, Please! When Jones was merely pondering a Democratic run for the Senate, he found that he already had a McConnell tracker following him; a private investigator was digging for dirt. McConnell himself captured the spirit of the operation in a secretly recorded 2013 meeting about a potential opponent. “When anybody sticks their head up,” he told his minions, “do them out.” To destroy the reputation of an opponent in the comprehensive way that McConnell prefers, it’s essential to have an overwhelming financial advantage to drown out the Democrat’s defenses. “As I always say,” McConnell writes in his 2016 memoir, The Long Game, “the three most important words in politics are ‘cash on hand.’” From the start, he’s been a relentless fundraiser, someone who does generous favors for his corporate and wealthy benefactors and, of course, expects generous returns from them. As former Republican senator Alan Simpson told McConnell’s biographer MacGillis, “When you raise the flag and somebody hollers from the back of the room, ‘Does anyone want to go to a fundraiser and raise some bucks?’ Mitch will be right there…. It’s a joy to him. He gets a twinkle in his eye and his step quickens.”

It’s this idiosyncrasy that allowed McConnell, possessed of none of the back-
slapping bonhomie that usually helps senators climb the leadership ladder, to move up through the years. He also became the most ardent foe of campaign finance reform in the chamber, even when it was being championed by fellow Republicans like John McCain. While others in the party were reluctant to speak out against the McCain-Feingold Act, the most ambitious effort to rein in political money in recent decades, McConnell took on the fight. After the bill passed, he challenged it in court and founded a legal center dedicated to overturning it, and his efforts bore fruit in the Citizens United decision that created the dark-money-driven chaos of today.

Not surprisingly, McConnell is pretty darn good at exploiting the system he did so much to create. In his two most recent races, he had $10 million and $12 million advantages over his Democratic opponents. Through the first two quarters of this year, he raised more than ever: $36 million, almost 90 percent of which came from out-of-state donors (aka Wall Street & Co.). Even so, McGrath raised more. Supplementing her efforts, the Ditch Mitch Fund, a PAC operated by political operative Ryan Aquilina, had raised $14 million by early September that will be used to go after McConnell on talk-radio stations in Kentucky, on Fox News and social media, and in other spots where Trump voters who dislike McConnell may roam. “There’s so much money coming in, for her campaign and our fund, that we’re able to get a little creative,” Aquilina says. “When you talk to people [in Kentucky] who voted for Trump, the reason they like him is the reason they hate McConnell. A lot of them still believe Trump is taking on the establishment; they all think McConnell is part of the swamp and just in it for himself.”

In the past, McConnell ran against experienced politicians with voting records, donors, allies, years of speeches, and financial disclosures that could be exploited and exaggerated. But McGrath spent almost her whole adult life either at the Naval Academy, where she later taught, or in the Marine Corps. She has three young children, she’s never been divorced, and her husband is a Republican. Team Mitch will find something to use on her, no doubt. But McGrath’s life doesn’t appear to offer much grist for the Team Mitch mill.

Since McGrath entered the race, McConnell’s campaign has been left to revive and repackage the two gaffes that Barr used against her in 2018. The campaign’s reaction to the news of her narrow win in June was typical: “Extreme Amy McGrath…is just another tool of the Washington Democratic establishment who has no idea what matters most to Kentuckians,” said McConnell’s campaign press secretary, Kate Cooksey. “It’s clear this self-proclaimed most liberal person in Kentucky who supports government-run health care and abortion even in the ninth month does not represent Kentucky values.”

This is stale, boilerplate stuff—unworthy, really, of a McConnell campaign. But that’s the same note it has been sounding for 13 months. And branding McGrath as a left-wing extremist is a harder sell after Booker and Mike Broihier, the other progressive candidate who challenged her in the Democratic primary, ran ads throughout May and June castigating her for being too moderate, too Trump-positive, and not even a real Democrat. In a sign that a screw is loose somewhere in McConnell’s campaign, Team Mitch released an attack ad in early July called “Reviews,” which quoted negative comments about McGrath during the primary campaign and had Booker castigating her for peddling “BS” to Kentuckians. “That’s a completely different argument than the one they’ve been making all along, that she’s too extreme,” Cross says.

While Team Mitch is apparently still searching for something to hit McGrath with that isn’t already well-worn, her campaign and the anti-McConnell PACs and groups have what can only be called an embarrassment of riches when it comes to angles of attack against him. Name any political sin you like, and the chances are exceedingly strong that McConnell—like the Democratic Senate leader of yore to whom he’s sometimes compared, Lyndon Johnson—has committed it repeatedly for four decades and counting.

While McGrath’s campaign for the Senate has already been left for dead twice, one close political observer who’s never stopped taking her seriously is her opponent. Team Mitch began hitting “Extreme Amy” the moment she stepped into the race (and then stepped in it), and McConnell’s refusal to miss a day of recess when he can be in Kentucky campaigning doesn’t suggest that he’s feeling a sense of blithe confidence about what awaits him this fall. Of course, he has never been one to take victory for granted; it’s one big reason he’s never experienced a defeat.

But in mid-July, there was one tangible sign that McConnell has his worries. The Senate Leadership Fund, run by McConnell’s former chief of staff, which raises megamillions to help other GOP senators fend off challenges (and keep them loyal to their leader), announced that it had bought $10 million worth of TV time in Kentucky for the fall. Soon after, another McConnell-affiliated PAC booked $4.5 million worth of airtime in Kentucky for August. “I know it’s a cliché,” Aquilina says, “but money speaks volumes. Why are national Republicans spending $15 million, so far, in a state that Trump won by 30 points? To take it away from Kansas and Montana and Colorado, that says a lot. Clearly, they think Kentucky’s a competitive state.” Maybe. But if it comes down to a choice between helping other Republicans who are struggling to hold onto their seats—or even the party’s majority in the Senate—and his own survival, McConnell has shown that he will choose the latter every time.

McConnell has his challenges—not least the fact that, as Senate majority leader without a functioning president, he can’t avoid doing some governing and legislating during a running national emergency. He won’t be able to avoid sharing the blame if the pandemic continues to rage out of control, especially if it spikes in Kentucky. Thus far it hasn’t, because of the steady leadership of Governor Andy Beshear, a Democrat who defeated incumbent Republican and Trump disciple Matt Bevin last fall. Beshear’s victory buoyed the hopes of Kentucky Democrats for 2020, but it’s a slender reed: His party still lost every other statewide election. “If anything, Kentucky is getting even more red,” wrote FiveThirtyEight contributor Perry Bacon Jr. last November after the off-year elections. But key suburban voters, who are rebelling against Trump all across the country, have been trending blue in Kentucky since 2014.

And McConnell is tethered to Trump, which is its own special hell. The senator looked decidedly uncomfortable during the Republican National Convention, appearing in a taped segment from a location identified only as “Kentucky.” After praising the president and boasting, “I work beside him every day,” McConnell segued into a litany of conspiratorial red meat. “They want to tell you what kind of car you can drive, what sources of information are credible, and even how many hamburgers you can eat.” He tried to chuckle.

Still, there’s no question that McGrath faces the longer odds. If Trump’s popularity doesn’t bottom out, she still has to persuade a lot of the president’s Kentucky fans to switch sides on the second line of the ballot. At the same time, she has to convince Booker’s fans that she’s worth bothering to vote for. That would be a tough combination for even the nimblest of politicians. But one advantage to the fact that she’s been in general-election mode since July of last year is that McGrath has had a lot of time to sharpen her message about McConnell.

Last summer, when I first interviewed her for almost an hour in her Lexington campaign office, McGrath was still figuring it all out. She still had awkward things to say about Trump and partisan boxes, and she meandered around policy questions. But whenever the talk turned to McConnell, she switched on. Suddenly she knew what she wanted to say, and she just said it. “I want guys like Mitch McConnell out because they’re making the rest of America cynical. The dysfunction, Bob! We’ve got an entire generation of young Americans that don’t know how a functioning government works. Because of him. He isn’t in the swamp. He is the swamp.

“His narrative has always been, ‘Look at me, I’m so powerful, I do so much for Kentucky.’ Meanwhile, we have the highest cancer rate in the country. One in four Kentuckians have diabetes. We have the second-highest per capita spending for prescription drugs in the country. We have an opioid crisis, where we have two times the death rate in comparison to the national average. And we have a senator who over and over again wants to throw people off health care! We have a senator who does not want to do any work on getting drug prices down. He’s bought off by Big Pharma.” And when his party had all the power and the presidency, what did he do? “He passed a massive tax windfall for people like him, for millionaires like him. That’s the only major piece of legislation that he did, Mr. Powerful Man.”

This version of Amy McGrath just might get somewhere, I thought. It took a while, but McGrath—who after her near pratfall in June replaced her original campaign manager with a former organizer for Barack Obama and Hillary Clinton—has become a sharper and more comfortable candidate, less prone to grasp for anodyne talking points. In July, she was a guest on The View and smiled her way through one of Meghan McCain’s characteristic attempts at a gotcha. Didn’t she think, McCain asked, that the reason she almost lost her primary had something to do with the fact that 96 percent of her contributions came from out of state? Did she really have any connection to Kentucky at all? Was that her problem? “Mitch McConnell gets about 95 percent of his money from outside of Kentucky, too,” McGrath snapped back. “My average donation is $35. And when that vet from Iowa gives me $25…he’s not handing me draft legislation at the same time.” The clip soon trended on Twitter, one year after the Kavanaugh mess. In a good way this time.