By Abigail Abrams
January 25, 2019

Roger Stone, a longtime informal adviser to President Donald Trump, was arrested by the FBI early Friday morning on criminal charges relating to Special Counsel Robert Mueller’s investigation.

Stone was charged with seven counts, including one of obstructing an official proceeding, five of making false statements and one of witness tampering.

The indictment is the first in 2019 as Special Counsel Robert Mueller continues to investigate Russian interference in the 2016 election and whether Trump’s campaign colluded with Russians.

Stone’s arrest is a significant blow to the President, as the self-described “dirty trickster” has been in Trump’s orbit for decades. He has been involved in many political controversies over the years and has worked for Republicans from Richard Nixon and Ronald Reagan to Senator Bob Dole and both Bushes.

But who exactly is Roger Stone?

A political operative steeped in Washington’s dark arts, Stone has known Trump since at least 1980, according to the New York Times. Stone was raised in Lewisboro, New York and moved to the nation’s capital to attend George Washington University. But the pull of politics was strong, and he was soon working for presidential campaigns and then starting his own political consulting business.

In the early 1970s, Stone played a small role in the Watergate scandal and tried to embarrass Pete McCloskey, a Republican challenging Nixon, by donating money in the name of the Young Socialist Alliance to McCloskey’s campaign. After these details came out during the Watergate hearings in 1973, Stone left his job on Senator Bob Dole’s staff but soon went to work for Ronald Reagan’s failed campaign in 1976 and his successful ones in 1980 and 1984.

When Reagan won the presidency in 1980, Stone started a firm with Charlie Black and none other than Paul Manafort, who would later go on to become Trump’s campaign chairman and also play a key role in the special counsel’s investigation.

The firm, originally called Black, Manafort, and Stone, performed a combination of lobbying, consulting and public relations for its clients. TIME called it “the ultimate supermarket of influence peddling” and the group’s clients included both major corporations and foreign dictators such as Angola’s Jonas Savimbi, according to The Atlantic.

How did he get involved with Trump?

Stone did lobbying work for Trump in the 1980s and became a strategist and confidante as Trump’s ambitions rose. When Trump was considering a third-party run for the presidency in the lead-up to the 2000 election, Stone directed the exploratory committee.

The two remained close, but they had similar brash manners of talking and sometimes clashed. A 2008 New Yorker profile of Stone, by Jeffrey Toobin, is perhaps most illustrative of this strange dynamic. At the time, Stone was an on-again-off-again adviser to Trump. But, asked about Stone, Trump wasn’t exactly enthusiastic. “Roger is a stone-cold loser,” Trump told Toobin. “He always tries taking credit for things he never did.”

Still, Stone continued working with Trump and as the 2016 cycle drew closer, he was ready to jump in to help his friend start a presidential bid for real this time.

What did he do for the Trump campaign?

When Trump announced he would run for president in June of 2015, Roger Stone served as one of his top political strategists. But by early August, Stone was out. Trump initially announced he was firing Stone, but Stone soon disputed this, say he quit the campaign over controversial comments Trump made about Megyn Kelly.

This fight prompted Trump to lump his adviser in with “publicity seekers who want to be on magazines or who are out for themselves.”

But even though Stone no longer had an official role in campaign, his feud with Trump did not last long. He remained in contact with Trump and encouraged him to hire Paul Manafort in March of 2016.

What is his involvement in the Russia investigation?

In 2016, Stone was publicly supportive when WikiLeaks released hacked emails that were damaging to Hillary Clinton and the Democratic National Committee. He also claimed many times that he was in contact with WikiLeaks founder Julian Assange and that he had advance warning of the leaks.

In the following months, Stone frequently changed his story, saying he never spoke to Assange and said that he did not have any knowledge that Russians were involved in the hacking.

In February of 2017, Stone spoke to TIME and was asked whether he had been contacted as part of the Russia investigation. “I have not been contacted by anybody in law enforcement. There is absolutely no foundation to this whatsoever,” he said. “The intelligence community could not have found email transmissions or financial transactions involving me and the Russians and the Trump campaign because there are none. I have no Russian clients. I have no Russian contacts. I have no Russian money. I have no Russian influences. I do like Russian vodka. This thing is a canard. Were the Russians hacking us? Maybe. But did they affect the election in any way? No.”

He also told TIME about his seeming awareness of what Wikileaks was up to: “I have a mutual friend who’s a journalist and was in London and communicated with him. When he came back, he told me that Assange has devastating political dynamite on Hillary Clinton and he’s going to begin releasing it. I asked when. He said as soon as Wednesday. So I posted that. That [Tuesday], Assange had a press thing where he announced they would have disclosures for the next 10 weeks. So everything I said was true.”

In late May, however, the Wall Street Journal also reported that Stone actively reached out to attempt to get specific information from Assange.

The special counsel’s indictment released on Friday furthers this by accusing Stone of giving information about WikiLeaks to the Trump campaign. According to the indictment, Stone told “senior Trump campaign officials” about hacked emails that could hurt Clinton, and once emails were released on July 22, 2016, the Trump campaign wanted to know more.

“A senior Trump Campaign official was directed to contact Stone about any additional releases and what other damaging information Organization 1 had regarding the Clinton campaign,” the indictment says, referring to WikiLeaks. “Stone thereafter told the Trump campaign about potential future releases of damaging material by Organization 1.”

The indictment does not accuse Stone of colluding with Assange or Russian officials, but it does say that, after the election, Stone lied to Congress to try to cover his actions. It also says Stone tried to persuade another witness, identified as “Person 2,” to refuse to cooperate with the House Intelligence Committee.

As the investigation has continued in recent months, Stone said publicly he was “prepared” to be indicted but maintained he had not done anything illegal.

Write to Abigail Abrams at abigail.abrams@time.com.

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