In Donald Trump’s America, unpredictability is the new normal. But for those trying to navigate the shifting landscape, a visit to Florida — and a conversation with Roger Stone — may offer a glimpse into the playbook.
Stone, notorious in the United States and largely unknown in Greece, has spent decades as the GOP’s shadow strategist. A master of provocation and political theater, he was one of the first to spot Trump’s potential — and helped build the myth before the rest of the world caught on.
The tactics he champions now echo across the Atlantic. Through his influence on Trump, Stone’s political DNA has touched not only American politics but international developments as well.
In the corner of the conference room where he is scheduled to appear sits a copy of his book, Stone’s Rules: How to Win in Politics, Business, and Style. A quick flip through the pages reveals the outlines of a familiar persona. Rules such as “attack, never defend” and “admit nothing, deny everything, launch a counterattack” feel like an operating manual for Trump himself.
As for the “style” promised on the book’s cover, it arrives in the form of the man who eventually strides into the room. Stone doesn’t resemble a traditional political strategist so much as a character from a forgotten noir film shot in Miami.
His voice, gravelly and commanding, precedes him. His outfit — a tailored double-breasted pinstripe suit, wide-legged trousers, a white pocket square, and two-tone shoes — completes the portrait of a man who sees politics as performance.
And if politics is theater, Roger Stone is a master of the stage.
Stone and Greece
Before the interview begins, Stone settles in and asks, with a breezy familiarity, how things are in Greece — a country he’s never visited but, he says, hopes to before the end of the year.
Stone’s career has been focused almost exclusively on domestic American politics, with limited forays into foreign policy. Still, he seems surprisingly informed about Greece. That familiarity comes through personal contacts — friends in Athens and prominent Greek-American businessmen who keep a lower profile than the usual names circulated in Greek-American circles.
Over the past year, Stone says, several figures from Greece’s political right — particularly from smaller parties orbiting the ruling New Democracy — have reached out to him. They’ve sought political advice, introductions to Trump-world figures, and a stamp of legitimacy from someone close to the former president.
While Stone was intrigued by the idea of seeing a political force in Greece aligned with the values of the MAGA movement, he ultimately chose not to get involved, noting that none of the individuals or parties who reached out felt like the right fit.
Karen Gonzalez Pittman, a State Rep. of the Florida House of Representative from the 65th district, shows her MAGA handbag before attending the Sunshine Ball in Washington, U.S. January 18, 2025. REUTERS/Shannon Stapleton
Unlike many names from Trump’s first term who have since faded, Stone remains in close touch with the president and continues to speak with key figures in his circle, including influential donors at Mar-a-Lago who retain Trump’s ear.
During the conversation, Stone repeatedly expresses political support for Greece. He argues that Washington should support “Greek maritime claims” and explore the possibility of new U.S. bases in the country. His tone sharpens when the topic turns to Turkey, which he calls a “frenemy” of the United States.
When asked about the current relationship between the Biden administration and the Greek government, Stone echoes a view held by some in Republican circles: Athens aligned too closely with the Biden administration over the past four years — particularly on the war in Ukraine. However, in reality, the Biden administration pressured Greece for far more concessions than it ultimately managed to secure.
Also, some of these Republican voices criticize what they view as the Greek government’s embrace of progressive social policies in coordination with Democratic officials. In these circles, the recent legalization of same-sex marriage in Greece is believed to have followed lobbying by top Democrats, including former House Speaker Nancy Pelosi, who reportedly made the request directly to the Greek prime minister.
Yet Stone insists he remains a friend of Greece, with a particular focus on the strategic ports of Alexandroupolis and Piraeus. Asked what Athens could do to elevate its profile in Washington, he doesn’t hesitate. “Your most strategic port is controlled by Communist China,” he says, referencing Chinese ownership stakes in Piraeus. He goes on to describe China as “the greatest threat to the U.S. — and the world.”
Though Stone holds no official government position and is careful to frame all of his comments as “strictly personal,” it’s clear he knows the weight his words can carry.
But for someone who has built a career on provocation and performance, his unusually measured tone stands out. Those who know him well take it as a sign: when Roger Stone stops performing, he may be preparing to act.
The Guilfoyle–Trump–Barrack Triangle
Roger Stone speaks warmly of Tom Barrack, the U.S. ambassador to Turkey, describing a personal friendship that dates back to 1972. But it is Kimberly Guilfoyle, Donald Trump’s nominee for ambassador to Greece, who draws his highest praise.
“I think she will entirely redefine the role,” he says. “People should know that she was an extremely successful prosecutor. She served in California, both in San Francisco and Los Angeles, and she never lost a case. And she was very famous for giving her summations completely from memory without notes. She is an extremely capable person and has the trust of the president. I think it is a sign of great appreciation for Greece that he sent one of his closest friends and not a career bureaucrat.”
Stone sees in the two appointments a rare opening: a channel for direct and personal communication across the triangle of Washington, Athens, and Ankara. He highlights the significance of having two of the president’s closest friends serving as ambassadors to Greece and Turkey.
“The fact that you have two of the president’s closest friends and allies in those two countries as ambassadors, I think, is pivotal,” he says. “Because not only can Kimberly Guilfoyle get the president on the phone, she can also get Tom Barrack on the phone, and vice versa. They are both enormously capable and very fair-minded.”
Trump’s Flirting with Erdogan and Kim Jong Un
Trump’s relationship with Erdogan is a subject Roger Stone says he hasn’t discussed directly with the former president. Still, he uses the opportunity to tell a story about two conversations Trump had following his 2016 election victory: one private, with Bill Clinton, and one public, with Barack Obama.
According to Stone, both former presidents warned Trump about the growing threat posed by North Korea. “The most dangerous problem you’re going to have is the crazy leader in North Korea who is very close to getting nuclear weapons,” they reportedly told him.
Stone recounts Trump’s reaction: “And he’s telling you?” he asked. “What do you mean… we’re not talking to him,” they said. Trump, Stone explains, couldn’t understand their logic. “Wouldn’t you like to have a dialogue with him to see what’s on his mind, and maybe you can convince him?” he asked. According to Stone, both Clinton and Obama advised him to stay away.
“But that wasn’t Trump’s approach,” Stone says. “And of course, his opening up to North Korea was one of the most historic moves he’s made. It was a move toward peace.”
He sees the same diplomatic instinct at play in Trump’s willingness to engage with Turkish President Erdogan. “He’ll talk to him. He’ll talk to everyone because he wants to get everyone’s input. And he believes you should pursue commerce over chaos. You should pursue negotiations over war. That’s why he got elected. He was elected as a peace candidate.”
Of course, North Korea is a hostile regime, whereas Turkey is a NATO ally—raising questions about whether Trump’s overtures toward Erdogan could be perceived as a reward, or worse, as indifference to destabilizing behavior within the alliance.
On this, Stone doesn’t offer a detailed answer. But he insists that Trump’s willingness to engage should not be seen as compromising Greece’s security interests. “I would not assume, just because Donald Trump is talking to someone, that that will cause him to show any bias,” he says. “I do not expect that to happen.”
The ‘Hawks’ and the War with the Deep State
Just days before Israel’s surprise strike on Iran, Roger Stone issued a warning: “There are NATO allies who are clearly trying to push us into war. There are elements of our own government trying to push us into war.”
The longtime political adviser and close Trump confidant spoke of what he calls a “deep state” — an entrenched group of officials and operatives within the U.S. government who, he claims, work against the interests of the American people.
Stone argues that the drive to escalate conflict isn’t coming solely from NATO, but also from within Washington itself. In contrast, he describes Trump as a leader committed to peace — someone who favors negotiation over prolonging war.
Before tensions flared in the Persian Gulf, Stone had already been warning of the consequences of escalation. “It’s easy for people to say, ‘Hit Iran,’” he says. “But the moment that happens, the Iranians will close the Strait of Hormuz — where a quarter of the world’s energy passes — and gas prices here will skyrocket. No one’s thinking about the implications.”
Stone frames Trump’s approach as pragmatic rather than provocative. He describes the former president as committed to avoiding a broader war — not because it’s easy, but because he believes in the possibility of a negotiated resolution, even under difficult circumstances.
A firm believer in his “America First” doctrine, Stone argues that the U.S. is carrying too much of the burden in Ukraine. “If the Europeans want war, let them pay their fair share,” he says. He also points to an earlier statement by President Biden, suggesting the Donbas could be ceded to Russia, to argue that a diplomatic resolution is still possible.
“I think he has made it very clear that he will stand up to the war hawks who are trying to push us into a war that will have repercussions far beyond what the American people see.”
Stone’s critique of what he sees as the deep state extends beyond foreign policy. He accuses the Federal Reserve of manipulating interest rates for political purposes.
“When inflation was exactly where it is now, they cut rates to help Joe Biden’s reelection,” he claims. “But now, because they don’t want to boost the economy under Donald Trump, they won’t cut. And they accuse Trump of acting politically. No, actually, Jerome Powell, who’s not an economist, he’s a lawyer, is not cutting rates because he’s being political and he wants to delay a boom economy under Trump.”
The portrait he draws is one of a president navigating entrenched resistance — not just from political opponents, but from his own former staff. One of the most prominent examples Stone points to is retired General John Kelly, Trump’s former White House chief of staff.
“Kelly thought his job was to block Trump’s agenda,” Stone says, referring to the controversial — and unproven — allegation that Trump disparaged fallen American soldiers. “There were 19 people in the room, and no one remembers him saying it. Do you know why? Because he never said it.”
The Man Who Saw Trump Coming
The story of Donald Trump can hardly be told without Roger Stone. Not only was he a longtime adviser and confidant, but — as Stone sees it — he may have been the one to plant the seed of political ambition.
The two first met in the late 1970s, when Stone was managing Ronald Reagan’s presidential campaign in New York. Trump, then an ambitious young businessman, joined the finance committee and, along with his father, helped raise $100,000 — a significant contribution at the time.
Their relationship endured, marked by personal loyalty and political alignment.
Stone was among the first to view Trump not just as a real estate magnate, but as a future political force. As he tells it, he first floated the idea of a presidential run as early as 1988, during a conversation in Trump’s Manhattan office.
“He was reading the New York Times,” Stone recalls, “and said, ‘Wow, Michael Dukakis and George H.W. Bush — that’s what it’s going to come down to? Those guys are both terrible. There’s got to be somebody better.’”
A young Stone with former president Richard Nixon.
Stone didn’t miss the opening. “I said, ‘There definitely is.’ And when he asked who, I told him, ‘I was thinking of you.’” Trump’s reaction was immediate: “‘You’re out of your mind,’” Stone remembers with a grin.
But Stone was serious. “He already had the stature — not just physical stature, though he could command a room — but also the independence, the courage, the stamina, and the open mind to be not just a great candidate, but a great president.”
He adds that Trump’s views on trade, military spending, and NATO were already taking shape. “He’s been saying that since the ’80s.”
A brief flirtation with a presidential bid in 2000 never fully materialized. Trump was not yet convinced, even as Stone continued to press the case. The idea returned in 2012 — but it wasn’t until 2016, Stone says, that both the moment and the man aligned. “The timing was right,” he reflects. “And the rest is history.”
Their bond extended well beyond politics, enduring through decades of political campaigns, media battles, and personal crises. When asked to recall the most difficult conversation he ever had with Trump, Stone pauses — then shifts to a moment of levity, delivered with the seriousness of a classified briefing.
“A lot of people think he has thinning hair. I saw him in the locker room after a golf tournament, and his hair was pulled straight back. I said, ‘Man, you look like a movie star. You should wear your hair like that.’” Trump, Stone says, looked at him and replied firmly: “I like it the way it is.”
Stone’s reply? “Roger that.”
