The Evolution of Lobbying Under Trump: Ches McDowell’s Rise in MAGA Politics
What comes to mind when you hear the word “lobbyist?”
My political education stems mostly from four completed seasons of House of Cards, so when I first set out to understand lobbying, I had to Google K Street. My interest piqued when I realized a friend we made toward the end of the campaign trail was a major player in D.C.’s lobbying world.
I don’t claim to be an expert on Washington’s inner workings, which is why this newsletter exists—to serve the politically curious but logically overwhelmed; those who may have skipped too many government classes, but grew up and wanted to understand how the deals shaping our country actually get made.
I always assumed lobbying was something sinister—shadowy backroom deals, corporate greed, and a faction of faceless power brokers deciding which bills pass, which industries thrive, and which policies are doomed. And while there’s some truth to that, I’m learning the reality is (thankfully) more complex.
Lobbying has been part of American politics since the beginning. The First Amendment guarantees the right to petition the government—with limits. President Ulysses S. Grant is credited with coining the term “lobbyist” to describe the well-dressed men who crowded the lobby of Washington’s Willard Hotel, waiting to approach him with their interests. What started as informal persuasion evolved into a structured industry—now an essential, albeit controversial, part of government negotiations.
Lobbying, as I’ve come to understand, is the strategic art of influencing government decisions by advocating for specific policies, industries, or interests. It involves direct engagement with lawmakers, government officials, and regulatory bodies to shape legislation, secure funding, or sway policy outcomes in favor of a particular cause. Lobbyists—who may represent corporations, unions, advocacy groups, or grassroots movements—use research, data, and political connections to present compelling arguments that align with their clients’ goals. While lobbying is often viewed as a backroom game of power and persuasion, at its core, it ensures that policymakers have the information and support needed to make decisions. From the local school board to the state wildlife agency, from the Department of Homeland Security to Congress and the president—at every level of government, someone is always doing something to influence support. Want to get a book in your kid’s school? That’s lobbying. Want to meet with your congressman to rename a post office? That’s lobbying, too. Even casually running into a senator at the grocery store and voicing concerns about gun violence—that’s a form of lobbying.
The difference is, professional lobbyists do it for a living. They get paid to advocate.
“Lobbying is the world's second oldest profession.” — Bill Press
Its importance stems from the fact that legislators are expected to vote on a vast range of issues—many of which they have little expertise in. Unless a member of Congress has spent decades in a specific field, such as banking, they are unlikely to be well-versed in every policy area they must vote on. From tax policy to the Second Amendment, abortion, vaccines, and even commercial aviation, lawmakers are required to make decisions on topics they may not fully understand.
This is where lobbyists provide value. They serve as subject matter experts, helping legislators navigate complex issues. For example, someone with deep knowledge of sports betting can answer questions and provide critical insights that lawmakers might not otherwise have access to. This role becomes especially important in a media environment that often distorts narratives. A perfect example is how the media labels RFK Jr. as “anti-vaccine” and “anti-science,” when in reality, the truth is far more nuanced. A lobbyist can step in, clarify misconceptions, and ensure that legislators are making informed decisions based on facts rather than media spin.
Lobbying—and politics as a whole—is ultimately a game of chess, not checkers. It requires strategy, foresight, and the ability to anticipate moves before they happen.
For those paying attention, 2025 feels very different. With the MAGA movement firmly entrenched, the old guard has lost its grip. The question now is: Who holds close ties to the president? And who are considered K Street’s leading “MAGA lobbyists?” We’ve heard of some of the strongest America First lobbyists, like Jeff Miller and Arthur Schwartz—but who else is there?
Enter Ches McDowell
A major player in conservative lobbying, McDowell was named one of the top 10 lobbyists in North Carolina by the North State Journal in every year they did the poll. His firm, Checkmate Government Relations, is now considered one of the top MAGA lobbying outfits, specializing in state and federal lobbying, national advocacy, public affairs, strategic consulting, and political intelligence.
Denise and I met Ches the same way we’ve met most people in this new orbit—through a series of introductions that pulled us deeper into a political underworld we were only beginning to understand. My first official introduction was on a falconry trip in upstate New York, hosted by Don Jr. and RFK Jr. Ches and Don Jr. were coming in from a NASCAR race in North Carolina with JD Vance. We bonded over the thrill of the hunt. A hawk landed on Don’s head; RFK chased a rogue bird into the brush; Hayes held out his arm and let one land there. Ches was clearly keen on the sport.
Despite spending an afternoon together, I didn’t ask what he did—I was too busy hounding Carolina Shriver for details on a recent family feud trailing RFK’s concession.* But in the weeks that followed, Denise and I kept running into Ches. We figured he was important—he wore great suits, trademarked alligator cowboy boots, and was always pacing around hallways on the phone with high-powered names on the other end.
*Ches recently hired Jackson Hines, Cheryl Hines’ nephew who worked as Bobby’s body man during the campaign trail.
Ask Ches:
Q: What’s your zodiac sign?
Ches McDowell: I’m a Libra, but I don’t love that because it sounds like “liberal.”
Q: Favorite restaurant in D.C.?
CM: Sushi Nakazawa.
Q: What would you say is Don Jr.’s best quality?
CM: His best quality is that you’d never know who he was unless you already knew. I’ll never forget taking a group to deer camp—he was the only one who washed dishes. I’ve seen him gut elk, cook, and even give my daughter shooting lessons.
Q: And his worst?
CM: He tells too many people “yes.”
Q: How would you describe lobbying to a kindergartener?
CM: Lobbying is educating people about nuanced issues from a position of trust and expertise.
Q: One album you’ll never tire of?
CM: Blue Clear Sky by George Strait or American Beauty by the Grateful Dead.
Q: Can you do the Trump dance?
CM: Of course—and so can all my kids.
Unlike the traditional K Street power players, McDowell didn’t come from a legacy D.C. family or an elite political background. Raised in rural North Carolina by two Democrats, he grew up hunting, fishing, and immersed in the culture of the South—far removed from Washington’s cocktail circuit. His political instincts developed young. By college, he was already working in the North Carolina state legislature for Senate Minority Leader Phil Berger, advising Republican leaders on strategy and legislative priorities. While working there, the Republican Party took the majority for the first time in over a century. Though he never intended to become a lobbyist, his passion for politics and government work led him down an unexpected path
After law school, he built a career as a successful attorney in federal bankruptcy court, but his true calling emerged in 2015 when he spearheaded the fight to legalize Sunday hunting in North Carolina. The experience gave him a taste for lobbying—navigating the legislative process, securing votes, and outmaneuvering opposition forces. That battle propelled him into the world of political influence, where he quickly became a force in state and federal politics.
Early on, McDowell understood the shifting political landscape better than most. He told key political figures close to Trump that if the election went the right way, he would need allies in Washington—true supporters on the lobbying side—because the traditional Republican establishment was no longer relevant. The old guard lobbyists—those who had worked for George W. Bush or John McCain—had lost their influence. The Republican Party had fundamentally changed, yet the major lobbying firms continued to rely on outdated connections to corporate clients who simply “checked the box” by hiring Republican operatives. But those Republicans no longer mattered in the new political reality.
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With Trump’s return, the lobbying landscape is shifting dramatically, as Ches predicted. Just as the media is scrambling to adapt to another Trump era, so are the K Street power players who opposed the MAGA movement the first time around. The shake-up is forcing the entire industry to rethink decaying strategies and expired connections.
In this era, it’s not enough to be a lobbyist—you have to believe in what you’re advocating for. These MAGA-aligned lobbyists aren’t just checking a box or chasing a paycheck; they’re fighting for a cause they deeply care about. For Trump’s political future, this is crucial. The success of his movement depends on having people in his corner who are as passionate about his vision as he is.
Trump’s first term exposed the weaknesses of establishment Republican lobbyists—many of whom bet against him in 2016, advising corporate clients to donate to Hillary Clinton in anticipation of a standard Democratic administration that would maintain the status quo. When Trump won, instead of adapting, they decided to wait him out, relying on old ties to entrenched swamp figures like Mike Pence, Rex Tillerson, John Kelly, and Mark Milley.
The old-school lobbying infrastructure simply couldn’t keep up with the speed and unpredictability of Trump’s political movement. Washington’s established firms, with their traditional ways of doing business, struggled to connect with a new, more dynamic political environment.
But MAGA lobbyists? In the second campaign, they were quick to adapt, bringing fresh energy and authenticity to the table. Their ties to Trump’s movement gave them the edge, and they’ve been able to reshape the way lobbying is done in Washington.
This shift highlighted the importance of having lobbyists who didn’t just claim party loyalty, but actually believed in the movement’s mission. When JD Vance—or whoever emerges as the leader—runs in four years, the movement would need real allies. It would need people who could raise money, strategize, and ensure that both the House and Senate remained aligned with the populist vision. This wasn’t just about individual campaigns; it was about securing a political infrastructure that would last.
The lobbying firms that had long dominated Washington were outdated because their relationships were outdated. Many of the people in the first Trump administration had been establishment figures with existing D.C. ties, not true outsiders aligned with the MAGA movement. That allowed traditional firms to continue operating successfully since they still had connections within agencies. After all, Trump had never truly “cleaned house” in Washington. But McDowell saw the need for something different—a lobbying force that actually represented the movement, not just the remnants of the old Republican establishment.
McDowell’s firm name is evident of how he views the profession—Checkmate reflects his view of lobbying as a strategic game. Those who understand the board, anticipate moves, and stay loyal to their alliances come out on top.
His relationship with Don Jr. is different than most. The two met on a bear hunting trip after Don expressed an interest in the activity, and bad weather forced them to bond (sans bear spottings) in the wilderness. Unlike many in close-knit political circles, McDowell never asked Don Jr. for favors or used their friendship for personal gain. Instead, he saw the gap in Republican lobbying—most firms were relics of the Bush/McCain era, disconnected from the new conservative base—and advised Don Jr. that if Trump won in 2024, the MAGA movement would need its own network of lobbyists: people who actually understood the movement and could expand its influence in Washington permanently.
And Don Jr. was on board—he has emerged as a loyal enforcer and the strongest ally of his father. In 2016, he was new to politics. In 2020, he honed his craft. In 2024, he witnessed the true evil executed against his family and helped deliver the White House for his father while establishing JD Vance as the future of the movement.
As it goes, a new generation of lobbyists emerges every four years—new faces, new players—but behind the scenes, the real influence often remains concentrated in just a few hands. According to Don Jr., he personally acknowledges only certain lobbyists: Ches, Jeff Miller, and Arthur Schwartz, to name a few. Whether or not that’s entirely accurate, it points to a larger truth—access and influence in Washington often come down to who has the president’s ear at any given moment.
Don Jr. on Ches
Q: How did you and Ches become good friends, and what sets him apart from other lobbyists?
Donald Trump, Jr.: Well, I saw you mentioned the three guys who are obvious in my world—Jeff Miller, Arthur Schwartz, and Ches. These guys were there from day one—not just in 2016, but on January 7, which I see as the second day one. Now, you see all these so-called Trump guys popping up—lobbyists trying to claim they’ve got inside access. And I’m thinking, Who? No one on our team has ever heard of them. But Jeff, Arthur, and Ches? They were there early and often. They’re steadfast, they’re loyal.
Q: So there’s a trust factor with that core crew?
DT: Exactly. And that’s the difference. A lot of people pretend they were in the trenches, but these guys actually were. They weren’t just looking for a payday or trying to ride the wave. They believe in America First. They weren’t just waiting around, hoping things would go back to “normal” in D.C.
Q: And Ches specifically—what makes him unique?
DT: He’s younger, he understands our world, and he puts in the work. He’s not relying on old-school D.C. connections that don’t mean anything in MAGA world anymore. He’s been in this for eight or nine years, and he gets it.
Q: You guys go way back?
DT: Yeah, I met him in 2015 or 2016, before all of this was even real. I went all in and pre-endorsed his brother before the Trump endorsement for Congress. Ches just understood what we were trying to do. He knew the people involved. He’s been in it long enough to navigate it all while still believing in the movement.
Q: Whats the story about the hunting trip?
DT: So, I bought a bear hunt at an auction in North Carolina. Ches comes up to me and says, You don’t actually want to go on that hunt. You want to go on this one with me. We hit it off right away. Now, we’ve got a farm together in North Carolina, we bring our kids out, and it’s become an annual thing.
And that’s the thing—these guys aren’t just in the photo-op game. They actually do the work. They believe in the cause. That’s what sets them apart.
McDowell won’t speak about his experiences lobbying Trump publicly, but one story he did share: securing his brother’s endorsement in a North Carolina congressional race. He tells of sitting in Mar-A-Lago with Don Jr., Susie Wiles, his brother Addison, and President Trump. He won’t give many details, but did share that the meeting lasted over an hour and spent significant time talking about snakes, as well as the hilarity of Don Jr. and Don Sr.’s relationship. He also recounts, and talks frequently about, the empathy President Trump showed his family during that meeting.
His younger brother, newly elected to Congress at just 30 years old, delivered his first speech on the House floor. The topic was deeply personal—the devastating impact of fentanyl, a tragedy their family knows firsthand. Their youngest brother died from fentanyl use, making the speech not just political, but profoundly emotional.
McDowell argues that only a select few in the lobbying world truly understand Trump’s movement and wield real influence. He points to a few, but specifically notes Jeff Miller of Miller Strategies and Arthur Schwartz as key players. He says Andy Surabian is the best in the business on the public affairs and consulting side. And of course, no one is better than Chris LaCivita on the campaign orbit (Chris LaCivita, Jr. works for Ches). Unlike the K Street crowd still clinging to outdated establishment connections, these firms are where traditional lobbyists now turn when they need real access to Trump-aligned figures.
A prime example of this strategic approach is his work with the Lumbee Tribe of North Carolina. The Lumbee Tribe, the largest Native American tribe east of the Mississippi River with 60,000 members, had historically been Democratic voters. However, in 2016, they shifted dramatically to Trump. Despite their size, they lack full federal recognition, which prevents them from receiving key benefits, such as the ability to put land into trust and establish casinos—privileges granted to federally recognized tribes like the Seminole or Choctaw.
McDowell had developed friendships with members of the Lumbee years ago and recognized their political significance in North Carolina. Their support played a major role in Donald Trump’s 2016 victory in the state. With 60,000 members voting overwhelmingly for Trump—after previously supporting Obama by a 60-40 margin—their shift helped secure Trump’s narrow win. If they had voted as they had in the past, North Carolina’s electoral outcome could have been different.
“Ches is the real deal. A lot of people pretend to have influence, but he has access, talent, and charisma: a triple threat.” — Kimberly Guilfoyle
McDowell has worked with the Tribe for the last 2 campaigns, helping bring President Trump to Robeson County, NC (where they are based) in 2020 and making him the first president to visit the Tribe. Don Jr., Eric, Lara, and many other surrogates have made multiple trips, culminating in a Day 3 Presidential Memo announcing the government’s support for full-federal recognition of the Lumbee Tribe.
While lobbying often gets a bad rap, McDowell sees it as a necessary and misunderstood force. Politicians, no matter how experienced, can’t be experts on every policy issue. Lobbyists fill the gaps, offering critical information and strategic guidance. He often points out that no matter how you feel about lobbyists, you have one working for you every day. Every industry, profession, consumer product, and political view has a lobbyist.
As Trump prepares to secure lasting relevancy in his political resurrection, McDowell is ensuring that MAGA’s influence in Washington isn’t just a political wave—but a lasting power structure he’s helping frame and secure.
My mother worked for a lobbyist at the state capitol in Sacramento. She used to lament the fact that when she told people that she worked for a lobbyist they most often would give her the side eye. Great article and it is a great reminder that there are good people everywhere if you care to look.
Fantastic article! Very informative 🇺🇸👏👏