Roger Stone’s New York intrigues

Longtime political dirty trickster Roger Stone had done many things during his six decades in politics, but his greatest feat yet came down to just keeping his mouth shut. President Donald Trump commuted on July 10 what would have been a 40-month sentence for Stone, who was convicted last year by a federal court on seven charges related to his obstruction of a congressional investigation into Russian interference in the 2016 election. While the longtime Republican operative could have answered a lot of outstanding questions about the relationship between Trump and Wikileaks, which released hacked emails in 2016 damaging to his Democratic opponent Hillary Clinton, Stone declined to tell prosecutors or Congress what he knew.

Over the last six decades, self-proclaimed political dirty trickster Roger Stone has come under scrutiny for a variety of reasons. But his impressive run as a master of the dark arts could be coming to an end now that he has been found guilty by a federal court in Washington, D.C. on seven charges related to his obstruction of a congressional investigation into Russian interference in the 2016 election. Stone could face as much as 20 years in prison, but will likely serve a much shorter prison term – assuming his longtime pal President Donald Trump does not pardon him beforehand. 

Stone was arrested in January at his house in Fort Lauderdale, Florida, and accused of covering up his role as a middle man between Trump’s 2016 campaign and WikiLeaks, which was found by U.S. intelligence to have released emails obtained by Russian intelligence hackers. The trial is just the latest dramatic turn in a career in which Stone has repeatedly popped up in some of the most infamous episodes in state and national politics, leading The New Yorker magazine’s Jeffrey Toobin to label him a “malevolent Forrest Gump.” 

An indictment unsealed by Mueller in January alleges that a top official with Donald Trump’s presidential campaign instructed Stone to contact WikiLeaks in order to get information about thousands of hacked emails that could damage the candidacy of Democratic nominee Hillary Clinton. Stone could face prison time if he is ultimately convicted of charges of obstructing justice, making false statements and witness tampering. 

Stone has denied the charges. But the allegations are well in line with his past work as a political operator. This includes stints working with political figures as reputable as 1996 Republican presidential nominee Bob Dole and President Ronald Reagan and as notorious as President Richard Nixon, mob lawyer Roy Cohn, and prostitution madam Kristin Davis, who ran as the Anti-Prohibition for New York candidate for governor in 2010. 

Through it all Stone, who lives part-time in Manhattan and was raised in Westchester County, has never ventured far from his roots as a New York political operative predisposed to political intrigue and subterfuge.

Here are some of the places Stone has popped up over the years in New York politics before he got entangled in the investigation into the Trump campaign’s involvement with Russia.

1960 – Fake news in school

The Lewisboro, New York, native got an early start in political trickery. As an elementary school student in 1960, he spread rumors among his classmates that Republican presidential nominee Richard Nixon wanted kids to go to school on Saturdays. Then as the vice president of the student body in high school, he engineered the ouster of the president so he could take over. When reelection time came, he had a solid strategy in place to ensure a second term, he told The Washington Post in a 2007 interview. ''I left nothing to chance,'' he said. ''I built alliances and put all my serious challengers on my ticket. Then I recruited the most unpopular guy in the school to run against me. You think that's mean? No, it's smart.''

1972 – Nixon’s reelection campaign

Though he had stumped for Sen. John F. Kennedy for president in 1960 in the lunchroom at school, Stone had become a diehard Republican by the early 1970s. This included a role in President Richard Nixon’s 1972 campaign where Stone – who would later get a tattoo of Nixon on his back – put to use his budding political sabotage skills. He used the pseudonym Jason Rainer to make a campaign donation in the name of the Young Socialist Alliance to Pete McClosky, who was challenging Nixon for the Republican nomination. Then Stone leaked a receipt of the contribution to a New Hampshire newspaper to damage the rival campaign. He also reportedly hired a Republican operative to infiltrate Democratic nominee Sen. George McGovern’s campaign. This all came to light during congressional hearings in 1973.

1980 – John Anderson campaign 

Stone moved up quickly through the Republican ranks in the 1970s, including stints on the Nixon campaign and as president of the Young Republicans, a position he won with the help of Paul Manafort. Then when Ronald Reagan was running for the presidency in 1980 against President Jimmy Carter, Stone teamed up with Roy Cohn, a sinister New York City lawyer best known for his association with Trump. Stone and Cohn worked together to help third-party candidate John Anderson secure the Liberal Party nomination in New York in order to draw votes away from Carter. They did this by reportedly passing on $125,000 to an attorney with contacts in the party.  "There's a suitcase," Stone has said. "I don't look in the suitcase … I don't even know what was in the suitcase ... I take the suitcase to the law office. I drop it off. Two days later, they have a convention. Liberals decide they're endorsing John Anderson for president. It's a three-way race now in New York state. Reagan wins (New York) with 46 percent of the vote. I paid his law firm. Legal fees. I don't know what he did for the money, but whatever it was, the Liberal Party reached its right conclusion out of a matter of principle."

1996 – The Bob Dole campaign

By the mid-1990’s Stone and Paul Manafort had sold the political consulting firm credited with ushering in an era of no-holds barred lobbying in Washington, D.C. In 1996, Stone volunteered as a spokesman for Sen. Bob Dole’s presidential campaign, but the arrangement would not last long. He resigned after the National Enquirer reported that Stone had solicited sexual partners for himself and his second wife though ads. 

1999 – Trump’s aborted Reform Party campaign

Stone had urged Trump, who he first began advising in the 1980s, for years to run for president. As the 2000 election approached, Stone took on the role of leading Trump’s exploratory committee. Though Trump ultimately did not run that year, the campaign orchestrated by Stone gave early hints of Trump’s unconventional approach to campaigning. ''Every Wall Street economist trashed our plan,'' Mr. Stone told The New York Times. ''A conventional politician would pull his hair out, but we love it!'' Attention, for better or worse, was paid.

2000 – The Florida Recount

Stone is not known as someone who apologizes easily; that’s the antithesis of his brand of politics. But he has expressed regret for his involvement in the Brooks Brothers Riot when he helped lead Republican protesters storming the Miami-Dade County election board, a key event that helped Republican candidate George W. Bush eventually prevail in the controversial recount that decided the race against Democratic candidate Al Gore. “When I look at those double-page New York Times spreads of all the individual pictures of people who have been killed (in Iraq),” Stone told The Daily Beast, “I got to think, 'Maybe there wouldn't have been a war if I hadn't gone to Miami-Dade. Maybe there hadn’t have been (sic), in my view, an unjustified war if Bush hadn't become president.' It's very disturbing to me."

2002 – Billionaire Tom Golisano gubernatorial run

Stone had an ax to grind with Gov. George Pataki after the state Lobby Commission accused Stone of wrongdoing. At issue was a radio ad that Stone produced on behalf of Trump’s casino interests. Eventually, Stone agreed to a $100,000 settlement, which Trump paid, without admitting wrongdoing, but he was nonetheless still angry. "This was their theory,” Stone told The New York Times. “If a state legislator has the radio on in the car and hears this ad on his way to the Capitol, you've influenced him, and that's lobbying. I mean, fuck you!" Then Stone tried to get some sense of revenge by working for Tom Golisano – a billionaire businessman who was running as the Independence Party candidate against Pataki for the third time – but it was not enough to deprive Pataki a third time.

2004 – Al Sharpton campaign

While Stone has mostly worked for Republicans, he did work with fellow New Yorker Al Sharpton during the civil rights activist’s longshot 2004 bid for the Democratic presidential nomination. Reporting at the time found that Stone played a key role in financing and staffing Sharpton’s campaign. “Sharpton’s almost penniless campaign has been sustained only by money given or raised by Stone or by Stone-arranged credit with consultants,” LA Weekly reported at the time. 

2007 – The New York state Senate

Stone worked for a time as an advisor to the Republican state Senate conference, but that came to an end after Stone was accused of threatening the father of then-Gov. Eliot Spitzer. A phone message left at the Manhattan office of Bernard Spitzer said that he would be “compelled by the Senate sergeant at arms” to testify about “shady campaign loans” he reportedly made during his son’s 1994 attorney general campaign. A private investigator later linked the call to a phone number associated with Stone’s wife at the time. Stone followed his normal approach when faced by scandal: deny, deny, deny. He countered the accusation by claiming that he was the victim of “the ultimate dirty trick” whereby allies of Spitzer supposedly broke into Stone’s apartment to make the call. 

2010 – The Kristin Davis for governor campaign

Stone served as campaign manager for “Manhattan Madam” Kristin Davis’ gubernatorial campaign on the Anti-Prohibition line. While Davis – who is most famous as the head of a New York City prostitution ring frequented by then-Gov. Eliot Spitzer – has remained a close friend of Stone, he did not have all of his political talents devoted to her campaign since he was also advising Republican Carl Paladino’s campaign at the time. “It’s pretty simple; I made an antecedent commitment to help Kristin Davis, but she’s a protest candidate,” Mr. Stone told The New York Times. “Paladino on the other hand has a chance to be elected governor, and I’d like to see him win. I support him, and I make no bones about that.”

2015 – Trump campaign

Stone had advised Trump at the beginning of the campaign as Trump struggled to be taken seriously. But Stone quickly left the campaign following disagreements with Trump during the rocky early days of his candidacy. “I terminated Roger Stone last night because he no longer serves a useful function for my campaign,” Trump said at the time. “I really don’t want publicity seekers who want to be on magazines or who are out for themselves. This campaign is not about them. It’s about victory and making America great again.”

2020 – Trump’s reelection

A return to the campaign trail could be in store now that Stone is a free man. Trump is fighting for his political survival as the death toll mounts from COVID-19 and Democratic candidate Joe Biden widens his lead in crucial battleground states. Who better to lend a helping hand than Stone, who arguably owes Trump a favor for what has been called “an act of staggering corruption.” It makes a lot of sense when you consider that Stone is just one of several Trump acolytes (remember former National Security Advisor Michael Flynn?) whose star has grown in the president’s eye because of all the legal trouble he has been in. Mueller can write all the op-eds he wants about how Stone remains a convicted felon who arguably damaged public faith in democracy, while threatening a witness’ dog – but such arguments might just make Trump want Stone by his side through November even more.