The Thrill of the Hunt

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These days, Ches McDowell is living in high cotton, with friends in stratospheric places and an exotically appointed new office in Washington, D.C. But nine years ago, on Day 3 of his first hunting trip with Donald Trump Jr., the young lobbyist felt like he “was going to throw up.” 

McDowell’s life up to that point read like the first half of a Faulkner novel by way of Duck Dynasty. He had gone from the son of small-town Eastern North Carolina Democrats to Make America Great Again acolyte. Back then, few experts believed Donald Trump would wind up in the White House. But McDowell did. When the then-27-year-old wasn’t hustling as a state government lobbyist, he headed up the North Carolina branch of Sportsmen for Trump.

A few weeks before the 2016 election, McDowell met Don Jr., an avid hunter, at Lexington’s annual Wine, Wheels & Wildlife dinner put on by the Congressional Sportsmen’s Foundation. 

Many operatives “surf the circuit,” skimming from one tony event to another, shaking hands, trading a splash of personal information, and developing a working acquaintanceship. But McDowell has always bet bold. 

During the event’s auction, Don Jr. bought a trip to hunt black bears in Eastern North Carolina. McDowell, sitting nearby, leaned over and advised him to forget that trip and come hunting with him instead.  

“He’s shameless, and he’s got courage, I’ll give him that,” said Ches’ younger brother Addison, now a freshman congressman. 

By the time Don Jr. made his return visit that December for the trip Ches McDowell proposed, he’d gone from son of a mogul to member of the First Family-elect. McDowell arranged for one of North Carolina’s most skillful guides, Mike Johnson, to lead the hunt, and for all of them to stay in a double-wide trailer at the 1,500-acre Outfall Farm in Hyde County.

“We bought fuzzy comforters and throw rugs and tried to make it comfortable,” Johnson said. “But it was still a double-wide trailer with holes in the floor.”    

Through cold rain, the hunting party—including Don Jr.’s Secret Service detail—roved the farm and surrounding woods in pursuit of black bears.  

Finding a black bear in Eastern North Carolina usually isn’t hard. The region is thick with some of the biggest on the planet. McDowell had bagged several “monsters” weighing between 400 and 500 pounds; he says he has since shot bears weighing nearly 700 pounds.  

And yet, now, three days into their exploit, no sign of bears. “I looked at Don,” McDowell said of his nauseous feeling, “and thought, ‘He probably thinks I’m full of crap.’” 

“He’s shameless, and he’s got courage, I’ll give him that.” 

U.S. Rep. Addison McDowell

But, as good hunters must, he kept his cool. They decided to stay one more day.

Overnight, the rain stopped. Finding tracks, the hunting party unleashed baying hounds. McDowell and Don Jr. (plus the Secret Service detail) pressed into the woods. 

In a clearing, they came upon a 374-pound male surrounded by dogs, out of options, McDowell recounted. Stepping within 4 feet of the animal, Don Jr. raised his .454 Casull revolver.

The bear, McDowell said, is now a rug. But it was just the beginning for the ambitious young lobbyist. 

The outings became an annual tradition. In 2021, McDowell and Don Jr.—who didn’t respond to requests for comment—invested in around 1,500 acres of farm land and wilderness in Tyrrell County near the tiny township of Gum Neck. They call the spread The Bear Store. While farmers grow corn there, McDowell and Don Jr. regularly visit with family and friends to hunt bears, deer, turkeys, and more.

The adventures continued far beyond North Carolina, including a consequential trip to Mar-a-Lago, widening McDowell’s connections and solidifying his MAGA credentials. With his canny mix of backroads-and-barbecue style and sharp political chops, he is an exemplar of how to make it in Trump’s Washington—and a test case for the MAGA crowd’s prospects after the president exits.  

“It’s pretty remarkable for someone in his business to have risen as fast as he has on the state level and certainly on the federal level,” said state Senate Democratic Whip Jay Chaudhuri. “When you talk about someone jumping from Raleigh to Pennsylvania Avenue—he doesn’t have many peers.” 

The MAGA Moment

When not tracking and shooting large animals or hand-carving duck decoys, Charles F. ‘Ches’ McDowell IV, now 35, runs Checkmate Government Relations. He founded the lobbying firm in Winston-Salem in 2023. Last December, he announced he was adding a D.C. office. 

The firm’s dozen-member staff includes Chris LaCivita Jr., whose father served as senior adviser on Trump’s winning 2024 campaign, and Jackson Hines, a nephew and former aide to Health and Human Services Secretary Robert F. Kennedy Jr.  

The White House didn’t respond to requests for comment. 

Checkmate and other MAGA-aligned firms “aren’t just checking a box or chasing a paycheck; they’re fighting for a cause they deeply care about,” conservative influencer Jessica Reed Kraus wrote in a Substack profile of McDowell’s group. She called Checkmate “one of the top MAGA lobbying outfits.”

Still, the paychecks don’t hurt. The firm’s clients, according to its website, include Philip Morris International, the Panama Maritime Authority, Eli Lilly, Novo Nordisk, and Juul, which produces the e-cigarette McDowell occasionally hits. 

The Canadian Broadcasting Corporation reported in February that a collection of that country’s provincial and territorial leaders known as the Council of the Federation hired Checkmate “to help it connect with U.S. officials in hope of averting a trade war.” 

In May, Checkmate registered to represent Greystone Investment and Management LLC, a Dubai-based firm, listing the country represented as Pakistan, according to Indian newspaper The Sunday Guardian and lobbying records.

Closer to home, the Lumbee Tribe in North Carolina hired Checkmate to help pursue long-sought federal recognition. Days into his new administration, the president signed an executive order directing the Department of the Interior to come up with a path forward. Meanwhile, UNC-Chapel Hill tapped Checkmate to help fend off cuts to its federal research funds, The Daily Tar Heel reported. 

“Ches certainly has an instinct for going after big game.”

Randolph Cloud, lobbyist

From foreign governments to major corporations, clients hire Checkmate to persuasively state their case to the policy makers that matter most. And McDowell has close connections to many of them. 

Kraus, the Substack influencer, met McDowell on a falconry trip last fall in upstate New York with Don Jr. and Kennedy. This was just days after McDowell and Don Jr. hosted JD Vance at a NASCAR race in Concord, NC. 

Kraus’ piece complimented McDowell’s “great suits” and featured a close-up of his alligator skin boots emblazoned with the North Carolina flag. He is stout and bearded and, in a slightly sandpapery voice, answers questions as adroitly as if he’d seen them in advance.

A Wall Street Journal profile in April called attention to his chunky belt buckle bearing the Checkmate logo. So far, though, he’s been shy about showing off the black letters of the tattoo reading “MAGA” on his upper left leg, which isn’t visible in business wear (though he described it to The Assembly). 

The Checkmate office in D.C., which includes a larger-than-life pop art take on Donald Trump’s 2023 mugshot, is on Pennsylvania Avenue, not far from the White House. Nearby is McDowell’s airy new condo, where he crashes when not at home with his wife and three kids in Welcome—or hunting somewhere between Hyde County, Botswana, and New Zealand. 

The strategy behind lobbying and hunting is similar, he says. “Whether it’s a deer or a turkey, you try to get them where you want. You need to convince a turkey to leave the woods—and make it his idea. How?

“Similarly, some politicians are over here,” he said, gesturing to his left. “You want them to move over here,” he gestured to his right. “It’s how you frame the argument.”   

The Cheesecake Incident

The Washington hoopla is a universe away—specifically, 380 miles—from where McDowell grew up in Chadbourn, a town that could be the poster child for the perceived “American carnage” that fires the MAGA furnace.

Following a string of manufacturing closings, Chadbourn’s population slumped 25 percent between 2000 and 2020, down to a little more than 1,500. Columbus County ranks as one of the poorest in the state. 

McDowell’s parents, C.F. and Martha, set up their household here in the 1990s. His father was pastor at Chadbourn Baptist Church and sometimes spent sunny days walking the town’s main street, stopping in each storefront to chat with the owner, from the ladies’ apparel shop to the auto garage. He brought along young Ches, who’d watch his father make friends.

“That main street was full of stores,” McDowell recalled. “Now when I go back, everything’s either a pawn shop or boarded up. It’s really awful.”  

While being a pastor’s son taught McDowell how to carry himself in social settings (“Preachers make the best politicians,” he said), life at home made him watchful and self-reliant. His mother, also a pastor, was dealing with an autoimmune condition that made it painful to move. 

McDowell often looked after Addison and their youngest brother, Luke. “My dad’s job was to be with my mom when she was in the hospital,” said Addison, now 31. Their grandmothers would watch the boys, but they often looked to Ches as a father figure. “He was very young to have to do that.”

Conversations at family dinners revolved around faith, sports, and politics, the brothers said. Though their parents were Democrats, they weren’t particularly partisan. Ches relished the opportunity to take an opposing point of view, poking away with questions. 

He traces his conversion to conservatism to a flash of insight on a visit to Baltimore. In his telling, the family was strolling to their motel after dinner at The Cheesecake Factory, leftovers in hand. A homeless man asked for change. His mother instructed Ches to give the man his boxed-up dessert. 

With McDowell still fuming about it later, the family matriarch offered a spiritual explanation, then pivoted to politics. Helping people, she said, is what Democrats do. “Well, if that’s what Democrats do, I’m a Republican,” Ches remembers telling her.

The family eventually moved to Davidson County. By high school, McDowell battled in the trenches as a center on the football team and avidly followed the politics of the George W. Bush era. 

As a political science major at North Carolina State University, he landed an internship in the office of state Senate GOP leader Phil Berger, then in the minority. While attending law school at Campbell University, McDowell moonlighted as an associate for lobbyist Randolph Cloud, a 40-year fixture of the General Assembly (and a registered Democrat). 

“Ches knows how to listen and to understand the political dynamics of a conversation,” Cloud said. “And he’s the best I’ve ever seen at multitasking. He can talk on the phone, send a text, post on social media, and eat lunch all at the same time.”

After graduation, McDowell clerked for David “Dink” Warren, a bankruptcy judge in the Eastern District of North Carolina. But he missed stalking the halls of the legislature. He hopped to the law firm of Kilpatrick Townsend & Stockton and built a lobbying practice until leaving in 2023 to launch Checkmate.  

Jim Perry, a Republican, served in the state Senate from 2019-2024 before hanging out his own lobbying shingle with former GOP lieutenant governor Dan Forest. He calls McDowell “creative and super shrewd” in thinking through political challenges—and, in the manner of a disciplined hunter, dogged. 

“I don’t think the guy sleeps,” Perry said. During the full-court press to legalize online sports betting in North Carolina, for example, Perry said McDowell “cobbled together” a coalition of interests and kept them together. The success of the push was one of the biggest stories of the 2023 legislative session. In the first year after online betting launched, North Carolinians wagered $5.5 billion.  

Various lobbyists at the state legislature have a take on McDowell. Given the sensitivity of political relationships, some were willing to share only anonymously. One said he can be “brash.” “There are other lobbyists with big clients,” another noted, “but they don’t go around in cowboy boots—they keep their heads down.”   

“Ches certainly has an instinct for going after big game,” Cloud said. “Be it in the field or in political circles.”

Talking to God 

McDowell took up hunting as a teenager. Some small-town kids dream of escaping to the big city. McDowell’s escape was the woods—listening, watching, calculating, waiting, and returning with a meal and a good story, hopefully. 

The thrill of the hunt can also tightly bond its enthusiasts. “When you’re not with your cell phone or your meetings, you let your mind relax, and everything is heightened,” said Johnson, the guide on McDowell’s 2016 trip with Don Jr. “It’s almost intoxicating. When you’re with someone, even a brand-new acquaintance, you’re on the same wavelength. It’s a kind of euphoria you share. You make a friend for life.” 

The quiet of the woods became a refuge for McDowell when his brother Luke died of a fentanyl overdose in October 2016 at 20 years old. 

Luke’s life had been bumpy, but in the dynamics of the family he had always played jester to his oldest brother’s alpha dog. “When Ches got going, Luke could always break him up with laughter,” their mother said. 

At his brother’s funeral, McDowell put on a brave face. In his eulogy, he said he found solace in the fact that Luke had been a born-again Christian and “voted early for Trump.” To truly process the loss, he took to the woods.

“I’d go sit in a tree stand at a little farm in Rockingham County from sunup to sundown,” he said, “and just listen and pray and talk to God and cry and grieve. Hunting is a form of church to me.” 

Mission to Mar-a-Lago

By 2023, Addison McDowell, then a lobbyist for Blue Cross Blue Shield of North Carolina and former aide to then-U.S. Rep. Ted Budd, had joined the hunts with Don Jr. Around Thanksgiving, Johnson took them to McNenny Ranch in South Dakota to hunt white-tailed deer, coyotes, pheasants, and the occasional prairie dog. 

While Ches McDowell told tall tales around the evening campfire, Addison said he mulled the possibility of running for Congress in District 6, which stretches southwest from the Triad to Kannapolis and Concord. The likely primary field included Bo Hines, who’d lost in 2022, and Mark Walker, who’d previously represented the district.   

Ches urged his brother on. So did Don Jr. Addison said he asked him point blank: “Can I get your father’s endorsement?” While the younger Trump couldn’t commit, he agreed to help facilitate a meeting. 

On December 12, Ches took a day away from an annual mountain lion hunt in Montana to rendezvous with Addison at Mar-a-Lago. On the way, the older McDowell noticed his brother’s five o’clock shadow. “I made him stop at a gas station,” Ches recalled, “buy a razor, and shave.” 

At Trump’s Palm Beach estate, Don Jr. greeted the pair and escorted them to the so-called library, though the brothers said it bore no books and looked more like a country club. Presiding over everything was a bullion-tinted portrait of an athletic young Trump in a tennis sweater.

The brothers said Susie Wiles, co-chair of Trump’s comeback campaign (and now White House chief of staff), asked the younger McDowell why he wanted to run for Congress.

Addison glided through his practiced pitch. At the end, he emphasized a personal note: “Ma’am, I’ve seen the impact of the fentanyl crisis. I’ve been personally impacted, and I’ve never seen any politician take it as seriously as Donald Trump. If I can go to Congress and prevent one mother from having to get the news as my mother did that her child has died, it will all be worth it.” 

Wiles, who didn’t respond to requests for comment, expressed her support and exited. Then they waited 15 minutes until aides announced the arrival of Trump, just off the golf course.

“When you talk about someone jumping from Raleigh to Pennsylvania Avenue—he doesn’t have many peers.” 

Jay Chaudhuri, N.C. Senate Democratic Whip

As the brothers tell it, the former president began by asking about Michael Whatley, a North Carolinian who two months later became chair of the Republican National Committee. He ribbed the younger Trump, jesting, “I’m my son’s hero, you know.” They talked about hunting, to which the McDowells said Trump quipped, “I hunt. For votes.” 

Finally, Addison made his appeal for an endorsement. “But how are you going to raise money?” Trump asked. “No one knows who you are.”

Ches jumped in. 

“Sir, I’ve helped raise millions for people,” he said. “Some of them I don’t even know. But I love this man,” he nodded to his brother. “So how far do you think I’ll go for him?”

Trump, they said, thought for a moment, then replied that he would endorse him that night. (The endorsement actually appeared on Truth Social the next day.)

As the meeting broke up and everyone stood, Trump inadvertently touched on a perennial point of teasing between the brothers, commenting appreciatively on Addison’s 6-foot-3 height. As they left, Ches, who is several inches shorter, sank a fist into his brother’s gut, doubling him over: “Who’s taller now?”

True to his word, Ches helped drum up nearly $1 million for the campaign and went door-to-door hunting for votes. Addison won a six-way GOP primary and, without a Democratic opponent, cruised to victory last fall.

Turkey Shoot

On a bright, cool Friday in April, Ches McDowell and two of his three kids dart around Martin and Bertie counties scoping potential prey. Turkey season opens for folks under 18 the following day, so they’re collecting intel on where to find “the strutters”—the big male birds.   

Motoring from field to field, McDowell, in a Trump-branded camo cap, points out favorite sights. Here’s the mom-and-pop service station where he introduced Don Jr. to Cheerwine. (“He said it tasted like cherry Dr Pepper.”) Here’s the clapboard cottage where people in the know place orders with a mysterious chef known only as The Collard Lady. (“Absolutely the best collard greens in the world.”)

After lunch at River’s Edge, a faded but busy restaurant on the banks of the Roanoke, he pays for his brood’s platefuls of fried herring with two-dollar bills. As the wait staff watches both perplexed and delighted, he peels off one after another—$58 worth—from a fat wad he keeps on hand “for tips. Because a dollar bill isn’t enough.” 

All day, his phone interrupts at a steady clip. Should an assistant buy a vintage Coca-Cola vending machine for the office featuring a life-size image of deceased NASCAR champ Dale Earnhardt? (Definitely.) Can Checkmate quickly turn around a proposal for a foreign government in need of lobbying services? (Most definitely.)

While business is booming, time may have MAGA in its sights. Trump is, by virtue of term limits, a lame duck. His administration is hurrying to notch wins before the midterm elections, which usually favor the party out of power. 

But the way McDowell scopes it out, MAGA is the Republican Party—with Vice President Vance next in line to lead. 

“You need to convince a turkey to leave the woods—and make it his idea.”

Ches McDowell’s philosophy on hunting and lobbying

Not all conservatives see it this way. Veteran political operator Charlie Black, 77, leapt from North Carolina to D.C. as an aide to Jesse Helms. He co-founded the lobbying shop BMSK, which included Paul Manafort and Roger Stone, and worked on the campaigns of every GOP presidential candidate from 1972 through 2016, when he backed Ohio Gov. John Kasich. 

“MAGA is not the Republican Party,” Black said. “MAGA is Donald Trump, period. The majority of House and Senate Republicans are not MAGA. They’re afraid of Trump. What he’s doing with Russia or Iran or tariffs—they hate that. MAGA’s going to be gone, and the mainstream Republican Party will be back. And I would not want to be JD Vance or anyone else trying to figure out what to do then.” 

The obvious move, Black said, is to build a wide base of contacts on Capitol Hill and eventually broaden Checkmate into a bipartisan shop. 

McDowell acknowledges this well-worn path for lobbyists hunting long-term success. But he’s in no hurry to do so. The real key to success, he thinks, is authenticity, a quality he carries like 14-point antlers on a 7×7 elk. “When I come into someone’s office, they know where I stand—there’s no hiding it,” he says. “That allows us to have a meaningful conversation.” 

For now, life is authentically, dirt-on-your-hunting-boots good, especially on the more than 9,000 acres of swampy, unspoiled wilderness that surround Devil’s Gut Rod and Gun Club, the four-story lodge at which McDowell and his kids are staying for the weekend. 

Along the Roanoke River, he spies a banded water snake curled thickly around a tree branch hanging over the dark, rolling water. McDowell’s sights fix on a hunk of driftwood jutting toward the snake’s perch. 

“I’m gonna get it,” he says. Not with a gun. With his bare hands. 

This variety of snake isn’t venomous. But it will bite.

Stepping from the bank onto the driftwood, McDowell finds his balance and creeps toward the snake. His kids’ eyes widen to the size of harvest moons. Even the lodge owner—an experienced woodsman—is watching. 

The hunter takes one careful step closer, raises his arm, and makes his move. 

Correction: An earlier version of this story misstated the number of points on a 7×7 elk’s antlers. This story also incorrectly said Addison McDowell lives in Whiteville.

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Billy Warden is a writer, journalist, TV producer, and marketing executive as well as two-time TEDx speaker. His work has been recognized with a Muse Creative Arts award, Telly awards, and a regional Emmy nomination. He is an avid swimmer and mixologist—though he never imbibes before doing laps.