Roger Stone: A Life of Scandals, Controversies and Crimes
- Daniel Holland
- Aug 30
- 6 min read
In American politics, certain names become shorthand for scandal. Nixon means Watergate. Clinton means impeachment. Trump means chaos. And Roger Stone? Well, Stone means dirty tricks.
Unlike most political operatives, who prefer working behind the curtain, Stone made himself the show. With his flamboyant three-piece suits, trademark wide-brimmed hats, and a self-styled air of theatrical villainy, Stone revelled in the spotlight. He once said, “It’s better to be infamous than never to be famous at all.” And that single line neatly sums up his entire career.
From teenage trickster to convicted felon, from Nixon’s shadow to Trump’s side, Stone has spent half a century dancing between power, scandal, and outright crime. His story is less about policies and more about manipulation, ego, and the relentless pursuit of attention.
A Teenage Trickster
Roger Jason Stone Jr. was born in 1952 in Norwalk, Connecticut. By all accounts, he was political from an early age. In his high school’s mock election, Stone pulled his first dirty trick: he spread a rumour that his opponent wanted to make students eat lunch at school every day, no matter what. It wasn’t true, but it worked. His candidate won.
That moment was formative. Stone learned that politics wasn’t always about ideas or truth, it was about perception, spectacle, and sometimes deception.
By 19, he was working for Richard Nixon’s re-election campaign, a role that would tie him to the Watergate scandal. Stone wasn’t a key player, but he wasn’t exactly innocent either. He was accused of acting as a political saboteur, funnelling funds to infiltrate and disrupt George McGovern’s campaign.
Most people ran from the shadow of Watergate. Stone embraced it. Years later, he even had Nixon’s face tattooed on his back, a bizarre act of loyalty to a disgraced president he called “one of the greatest political minds of the century.”
The Lobbyist Years and Dictator Clients
After Nixon, Stone pivoted to lobbying. In the 1980s, he co-founded the powerhouse firm Black, Manafort, Stone & Kelly, alongside Paul Manafort and Charles Black. The firm quickly became infamous in Washington for representing some of the world’s most controversial leaders.
Clients included Ferdinand Marcos of the Philippines, who was ousted after years of corruption and human rights abuses, and Mobutu Sese Seko of Zaire, a dictator who plundered his country’s wealth while millions starved.
Stone had no qualms about this. He saw it as business. In fact, the firm earned the nickname “the torturers’ lobby.” For Stone, it was proof that in politics, money and influence mattered far more than morality.
This period cemented his reputation as someone willing to work for anyone, so long as the price was right.
Scandals in the Private Sphere
By the 1990s, Stone’s appetite for risk extended into his private life. In 1996, during Bob Dole’s presidential campaign, tabloids exposed personal ads in swingers’ magazines placed by Stone and his wife. The ads sought partners for group sex, complete with explicit detail.
Dole’s campaign swiftly cut Stone loose, embarrassed by the scandal. For many consultants, this would have been career suicide. But Stone styled himself as a libertine and shrugged it off. He insisted that his private life was irrelevant to his work, though the story followed him for years.
It was a reminder that Stone never shied away from the outrageous. If anything, he leaned into it.
The Trump Connection
Stone first crossed paths with Donald Trump in the 1980s, when Trump was a flashy New York real estate mogul with political ambitions. Stone recognised Trump’s potential immediately. He once said: “Trump has the aura, the charisma, the confidence. He’s a star.”
Stone encouraged Trump to run for president as early as 1988, and though the timing wasn’t right, their friendship endured. Stone became an informal adviser to Trump over the years, a role that suited him perfectly: whispering in the ear of a man who thrived on controversy.
In 2015, Stone briefly joined Trump’s presidential campaign but clashed with other staff and was pushed out. Still, he remained close, advising Trump from the outside and positioning himself as one of the campaign’s fiercest defenders.
The Russia Investigation and His Criminal Convictions
When Special Counsel Robert Mueller launched his investigation into Russian interference in the 2016 election, Stone suddenly found himself in the crosshairs. The probe revealed that Stone had acted as an informal go-between for the Trump campaign and WikiLeaks, which released hacked emails damaging to Hillary Clinton.
Stone lied to Congress about his contacts, pressured witnesses to back up his story, and obstructed the investigation. In January 2019, FBI agents dramatically arrested him in a pre-dawn raid at his Florida home.
By November 2019, a jury found him guilty on seven felony counts, including witness tampering and obstruction. He faced up to nine years in prison. In February 2020, he was sentenced to 40 months.
But Stone’s story didn’t end there. In July 2020, President Trump commuted his sentence, sparing him prison time. And in December 2020, Trump issued him a full pardon.
For Stone, it was the ultimate reward for loyalty. For critics, it was proof that corruption had reached the Oval Office.
Conspiracy Theories and Extremist Ties
After his pardon, Stone reinvented himself as a star of the far-right media circuit. He became a regular on Alex Jones’ InfoWars, spreading conspiracy theories about election fraud, the “deep state,” and shadowy plots against Trump.
Stone’s most bizarre claim came after the 2020 election. In December of that year, he suggested that North Korea had shipped thousands of ballots into the United States by boat to help Joe Biden. There was no evidence, of course, but Stone never needed evidence. He needed headlines.
His claim became part of the flood of misinformation that stoked anger among Trump supporters, setting the stage for the January 6th Capitol riot.
On that day, Stone was photographed with members of the Oath Keepers militia, who acted as his personal security detail. While he denied involvement in the riot itself, his links to extremists raised serious questions about his role in encouraging the chaos.
Stone’s Rules and His Political Philosophy
Stone likes to say that politics is a form of combat. In his 2018 book Stone’s Rules: How to Win at Politics, Business, and Style, he laid out his philosophy. Among his “rules” were lines like:
“Politics is not about uniting people. It’s about dividing people. Getting your 51 percent.”
“Admit nothing, deny everything, launch counterattack.”
These weren’t just words, they were his playbook. For Stone, the goal was always to win, no matter the cost. Truth, fairness, or morality were secondary.
This explains why Stone could go from Nixon to Reagan to Trump, and even flirt with third-party candidates like Gary Johnson. His loyalty wasn’t ideological. It was to power itself.
The Long Shadow of Scandal
Roger Stone’s career is a litany of scandals:
Watergate (1972): Accused of political sabotage at just 19.
Lobbying Dictators (1980s): Represented brutal regimes for profit.
Swinger Scandal (1996): Forced out of Dole’s campaign after tabloids exposed personal ads.
Trump Campaign (2016): Accused of serving as a backchannel to WikiLeaks.
Criminal Conviction (2019): Found guilty of obstruction and witness tampering.
Pardon (2020): Rescued by Trump despite felony convictions.
Conspiracy Theories (2020–present): Spread baseless claims about voter fraud, including blaming North Korea.
For Stone, each scandal became a stepping stone, keeping him in the headlines. As he once said, “There’s no such thing as bad publicity.”
Conclusion: The Trickster’s Legacy
Roger Stone has never held high office, written major legislation, or passed meaningful reforms. And yet, his fingerprints are all over American politics. From Nixon to Trump, he has been a shadowy presence, whispering strategies, planting rumours, and stirring chaos.
To his admirers, he’s a political genius, a man unafraid to fight dirty in a system where everyone bends the rules. To his critics, he’s the embodiment of corruption, a trickster who has poisoned democracy for decades.
Either way, his legacy is undeniable. Roger Stone is not remembered for building, but for breaking; not for healing, but for dividing. And perhaps that was always the point.
As one journalist once put it: “Stone doesn’t play the game of politics. He plays the game of scandal.”
Sources
Roger Stone, Stone’s Rules: How to Win at Politics, Business, and Style (2018)
“Roger Stone is Convicted in Trial That Revived Questions About Trump and Russia” – New York Times, 15 Nov 2019 – https://www.nytimes.com
“Roger Stone, Trump Ally, Sentenced to 40 Months” – NPR, 20 Feb 2020 – https://www.npr.org
“The Rise and Fall of Roger Stone” – The Atlantic, 2019 – https://www.theatlantic.com
“Roger Stone and the Dark Arts of Politics” – BBC News, 2019 – https://www.bbc.com
“Roger Stone Suggested North Korea Shipped Fake Ballots into the U.S.” – Newsweek, Dec 2020 – https://www.newsweek.com
