A key witness in Mueller's Russia probe had 'a lengthy conversation' with Trump at Mar-a-Lago

  • James Woolsey, a former CIA director who has been cooperating with the special counsel Robert Mueller, had a "lengthy conversation" with President Donald Trump over dinner last weekend at Trump's Mar-a-Lago resort.
  • Woolsey, who served on the board of Michael Flynn's lobbying firm, Flynn Intel Group, was at a meeting on September 19, 2016, with Flynn and Turkish government ministers at which they discussed removing the controversial Muslim cleric Fethullah Gulen from US soil.
  • Mueller's team has interviewed Woolsey about that meeting and has been in touch with the FBI since before Mueller's office began overseeing the Russia probe in May.

Former CIA Director James Woolsey dined with President Donald Trump last weekend at his Palm Beach Mar-a-Lago estate, where a report said they had a "lengthy conversation" at the main dining table surrounded by several of Trump's friends, associates, and political allies.

A tipster told Politico's Playbook about the conversation, which raised eyebrows given Woolsey's centrality to special counsel Robert Mueller's investigation of former national security adviser Michael Flynn.

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Key players in Trump-Russia connection allegations
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Key players in Trump-Russia connection allegations

Paul Manafort

Paul Manafort signed on as Donald Trump's campaign manager in March 2016. A longtime Republican strategist and beltway operative, Manafort had previously served as an adviser to former Ukrainian president Viktor Yanukovich -- a pro-Russia leader who was violently ousted in 2014. Manafort resigned from his campaign position in August 2016 amid questions over his lobbying history in Ukraine for an administration supportive of Russia. The former campaign manager reportedly remained in Trump's circle during the post-election transition period.

Michael Flynn

Gen. Michael Flynn was named President Trump's national security adviser in November of 2016. Flynn reportedly met and spoke with Russian Ambassador Sergey Kislyak in December, at one point discussing sanctions. Flynn originally told Vice President Pence he did not discuss sanctions -- a point the Department of Justice said made the national security adviser subject to blackmail. Flynn resigned from his position in February.

Sergey Kislyak

Outgoing Russian ambassador to the United States Sergey Kislyak is the Russian official U.S. attorney general Jeff Sessions -- communication Sessions denied during his Senate committee hearing testimony.

R. James Woolsey

Woolsey, the former director of the Central Intelligence Agency (CIA), has cooperated with Mueller's investigation and worked with Michael Flynn and was present at a meeting where they discussed removing the controversial Turkish Muslim cleric Fetullah Gulen from US soil. 

(Christopher Goodney/Bloomberg via Getty Images)

Roger Stone

Stone is a longtime Republican political consultant who served as a campaign adviser to Trump who continued to talk with the then-GOP candidate after stepping away from his adviser role. Stone claimed last year that he had knowledge of the planned WikiLeaks release of emails pertaining to Hillary Clinton and the Democratic National Committee. Stone recently admitted to speaking via direct message with "Guccifer 2.0" -- an online entity U.S. officials believe is tied to Russia. Stone says the correspondence was “completely innocuous.”

Jeff Sessions

Former U.S. senator Jeff Sessions from Alabama joined Trump's campaign as a foreign policy adviser in February 2016. Sessions was nominated to be U.S. attorney general by President Trump and was then confirmed by the Senate. Reports then emerged that Sessions had spoken twice with Sergey Kislyak while he was senator -- a fact that he left out of his Senate hearing testimony. Instead, he said in writing that he had not communicated with any Russian officials during the campaign season. Sessions defended himself saying he had spoken with Kislyak specifically in a senate capacity.

Russian President Vladimir Putin

The American intelligence community accused Putin in Jan. 2017 of ordering a campaign to undermine trust in the American electoral process, developing a clear preference for Trump as president. "We assess Russian President Vladimir Putin ordered an influence campaign in 2016 aimed at the US presidential election. Russia's goals were to undermine public faith in the US democratic process, denigrate Secretary Clinton, and harm her electability and potential presidency. We further assess Putin and the Russian Government developed a clear preference for President-elect Trump," the report read.

James Comey

Comey publicly confirmed in March an FBI inquiry into Russia's involvement in the 2016 election. “The F.B.I., as part of our counterintelligence effort, is investigating the Russian government’s efforts to interfere in the 2016 president election,” Comey stated.

Carter Page

Page worked for Merrill Lynch as an investment banker out of their Moscow office for three years before joining Trump's campaign as a foreign policy adviser. During his time with Merrill Lynch, Page advised transactions for two major Russian entities. Page has called Washington "hypocritical" for focusing on corruption and democratization in addressing U.S. relations with Russia. While Page is someone Trump camp has seemingly tried to distance itself from, Page recently said he has made frequent visits to Trump Tower.

J.D. Gordon

Before Gordon joined the Trump campaign as a national security adviser in March 2016, he served as a Pentagon spokesman from 2005 through 2009. Like others involved in Trump-Russia allegations, Gordon met with ambassador Kislyak in July at the Republican National Convention, but has since denied any wrongdoing in their conversation. He advocated for and worked to revise the RNC language on and position toward Ukraine relations, so it was more friendly toward Russia's dealings in the country.

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Woolsey, who served on the board of Flynn's lobbying firm Flynn Intel Group, was present at a September 19, 2016, meeting with Flynn and Turkish government ministers, where they discussed removing the controversial Muslim cleric Fetullah Gulen from US soil. 

Woolsey apparently notified Vice President Joe Biden through a mutual friend about the meeting, which he thought could have been an illegal discussion, Woolsey's spokesman Jonathan Franks said earlier this year.

Franks confirmed late last month that Mueller's team had interviewed Woolsey about the meeting. He noted that Woolsey and his wife have been in touch with the FBI since before Mueller's office began overseeing the Russia probe in May. 

"Ambassador Woolsey and his wife have been in communication with the FBI regarding the September 19, 2016, meeting Ambassador Woolsey was invited to attend by one of Gen. Flynn's business partners," he said in a statement. "Ambassador Woolsey and his wife have responded to every request, whether from the FBI, or, more recently, the Office of the Special Counsel."

Woolsey's participation in both that meeting with Flynn and Turkish government ministers and another meeting the next day with two Turkish businessmen — during which he reportedly pitched his own $10 million contract to help discredit Gulen — may have landed him on the FBI's radar even before Trump won the presidential election. 

Now, Mueller has reportedly gathered enough evidence against Flynn and his son to charge them with crimes related to their unregistered lobbying work for Turkish government interests.

Legal experts have speculated that Mueller may be leveraging the threat of an indictment against Flynn and his son to get them to cooperate with the broader investigation into whether Trump's campaign team — for which Flynn was a top surrogate — colluded with Russia, and whether Trump sought to obstruct the Russia probe when he fired former FBI Director James Comey in May.

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Retired Army Lt. Gen. Michael Flynn
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Retired Army Lt. Gen. Michael Flynn
National security adviser General Michael Flynn delivers a statement daily briefing at the White House in Washington U.S., February 1, 2017. REUTERS/Carlos Barria

Retired Lt. Gen. Michael Flynn arrives at the Trump Tower for meetings with US President-elect Donald Trump, in New York on November 17, 2016.

(EDUARDO MUNOZ ALVAREZ/AFP/Getty Images)

Retired United States Army lieutenant general Michael T. Flynn introduces Republican Presidential nominee Donald J. Trump before he delivered a speech at The Union League of Philadelphia on September 7, 2016 in Philadelphia, Pennsylvania. Trump spoke about his plans to build up the military if elected. Recent national polls show the presidential race is tightening with two months until the election.

(Photo by Mark Makela/Getty Images)

Retired Lt. Gen. Michael Flynn, at podium, and Republican presidential candidate Donald Trump attend a campaign event with veterans at the Trump International Hotel on Pennsylvania Ave., NW, where Trump stated he believes President Obama was born in the United States, September 16, 2016.

(Photo By Tom Williams/CQ Roll Call)

WASHINGTON, DC - FEBRUARY 01: White House Press Secretary Sean Spicer (L) yields the briefing room podium to National Security Adviser Michael Flynn February 1, 2017 in Washington, DC. Flynn said the White House is 'officially putting Iran on notice' for a recent missile test and support for Houthi rebels in Yemen. (Photo by Win McNamee/Getty Images)

Army Lt. Gen. Michael Flynn, director of the Defense Intelligence Agency, prepares to testify at a Senate Armed Services Committee hearing in Dirksen Building titled 'Current and Future Worldwide Threats,' featuring testimony by he and James Clapper, Director of National Intelligence.

(Photo By Tom Williams/CQ Roll Call)

White House National Security Advisor Michael Flynn (C) arrives prior to a joint news conference between Canadian Prime Minister Justin Trudeau and U.S. President Donald Trump at the White House in Washington, U.S., February 13, 2017. REUTERS/Carlos Barria
U.S. National Security Advisor Michael Flynn boards Air Force One at West Palm Beach International airport in West Palm Beach, Florida U.S., February 12, 2017. REUTERS/Carlos Barria
National security adviser General Michael Flynn arrives to deliver a statement during the daily briefing at the White House in Washington U.S., February 1, 2017. Picture taken February 1, 2017. REUTERS/Carlos Barria
White House National Security Advisor Michael Flynn (L) arrives at Joint Base Andrews, Maryland, U.S., February 10, 2017. REUTERS/Carlos Barria
WASHINGTON, DC - FEBRUARY 10: (AFP OUT) White House National Security Advisor Michael Flynn (R) walks down the West Wing Colonnade following a bilateral meeting between U.S. President Donald Trump and Japanese Prime Minister Shinzo Abe February 10, 2017 in Washington, DC. Trump and Abe are expected to discuss many issues, including trade and security ties and will hold a joint press confrence later in the day. (Photo by Chip Somodevilla/Getty Images)
ATLANTA, GA - FEBRUARY 02: (L-R) SCAD Dramatic writing professor Chris Auer, Producer Sandra Leviton, Executive producer and writer Michael Flynn, Tv literary agent Jeff Greenberg and Literary manager and producer Kaila York speak on stage during the 'Inside the Writers Room' event on Day One of aTVfest 2017 presented by SCAD on February 2, 2017 in Atlanta, Georgia. (Photo by Vivien Killilea/Getty Images for SCAD)
Lieutenant General Michael Flynn (ret.), National Security Advisor Designate speaks during a conference on the transition of the US Presidency from Barack Obama to Donald Trump at the US Institute Of Peace in Washington DC, January 10, 2017. / AFP / CHRIS KLEPONIS (Photo credit should read CHRIS KLEPONIS/AFP/Getty Images)
Retired Lieutenant General Michael Flynn, U.S. national security advisor, attends a swearing in ceremony of White House senior staff in the East Room of the White House in Washington, D.C., U.S., on Sunday, Jan. 22, 2017. Trump today mocked protesters who gathered for large demonstrations across the U.S. and the world on Saturday to signal discontent with his leadership, but later offered a more conciliatory tone, saying he recognized such marches as a hallmark of our democracy. Photographer: Andrew Harrer/Bloomberg via Getty Images
WASHINGTON, DC - JANUARY 20: Michael Flynn walks out after a morning worship service on Inauguration day at St. John's Episcopal Church in Washington, DC on Friday, Jan. 20, 2017. (Photo by Jabin Botsford/The Washington Post via Getty Images)
WASHINGTON, DC - JANUARY 20: Attorney General nominee Sen. Jeff Sessions (R-AL) (R), talks with National Security Advisor Michael Flynn inside of the inaugural parade reviewing stand in front of the White House on January 20, 2017 in Washington, DC. Donald Trump was sworn in as the nation's 45th president today. (Photo by Mark Wilson/Getty Images)
Retired Lieutenant General Michael Flynn, White House national security adviser-designate, center, stands in an elevator at Trump Tower in New York, U.S., on Thursday, Jan. 12, 2017. Donald Trump is slated to meet with AT&T Inc.'s top executives on Thursday to discuss the company's proposed $85.4 billion bid for Time Warner Inc., according to people familiar with the matter. The president-elect has said he opposes the deal. Photographer: John Taggart/Bloomberg via Getty Images
WASHINGTON, DC - JANUARY 20: Donald Trump's National Security Adviser Gen. Michael T. Flynn (R) arrives on the West Front of the U.S. Capitol on January 20, 2017 in Washington, DC. In today's inauguration ceremony Donald J. Trump becomes the 45th president of the United States. (Photo by Drew Angerer/Getty Images)
Lieutenant General Michael Flynn (ret.) and National Security Advisor Designate and Ambassador Susan Rice, National Security Advisor during a ceremonial passing of authority while participating in a conference on the transition of the US Presidency from Barack Obama to Donald Trump at the US Institute Of Peace in Washington DC, January 10, 2017. / AFP / CHRIS KLEPONIS (Photo credit should read CHRIS KLEPONIS/AFP/Getty Images)
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Flynn was forced to resign as national security adviser in early February when reports surfaced that he had spoken with former Russian ambassador Sergei Kislyak about US sanctions on Russia several times during the transition.

Franks was not immediately able to comment about what Woolsey and Trump discussed over dinner last weekend. But the conversation will likely be of interest to investigators scrutinizing Flynn, to whom Trump has reportedly remained loyal, and examining why Trump asked Comey shortly after Flynn resigned if the FBI would consider dropping the investigation into Flynn.

"Whenever a subject of a criminal investigation talks to a witness, the prosecution will ask questions about what was discussed during that meeting," said former federal prosecutor Renato Mariotti. The subject, in this case, is Trump, he said, while the witness is Woolsey.

Woolsey abruptly resigned from his position as a senior adviser to Trump's transition team in January, one day before Trump was set to receive a conclusive briefing from US intelligence officials on Russia's election interference.

The Washington Post reported at the time that Woolsey became uncomfortable after being cut out of intelligence talks between Trump and Flynn, and that he was taken aback by Trump's reported plans to restructure the CIA. 

"The campaign was over, and I didn't want them to keep saying that I was a senior adviser on the transition because I really wasn't," Woolsey told then-Fox News anchor Megyn Kelly in his first post-resignation interview. "I was not really called upon to go to meetings or participate in work on the transition."

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