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This week, he found himself in the middle of perhaps his most intriguing Trump-related story yet, due to a newly revealed connection to Rob Goldstone, the entertainment publicist who set up a meeting between top Trump campaign officials and Russians linked to the Kremlin during the thick of the 2016 campaign.
A source with direct knowledge of the matter explained to CNBC the connection between Scaramucci, founder of investment firm SkyBridge Capital, and Goldstone, whom Scaramucci considers "a good guy." The financier also met Goldstone "a few times" before he wrote an email to him that was made public Wednesday, said the source, who declined to be named.
The email in question, sent days after Trump appointed Scaramucci as White House communications director, was buried among more than 2,500 pages of documents pertaining to the June 2016 meeting.
The message from Scaramucci to Goldstone, dated July 23, 2017, came nearly two weeks after reports emerged that Goldstone had played a central role in setting up the Trump Tower meeting, which was led by Donald Trump Jr. Trump Jr. was promised details about Democratic presidential candidate Hillary Clinton that "would be very useful to" his father, but no such information is said to have surfaced.
The gathering is under scrutiny amid investigations into whether the Trump campaign colluded with Russian agents to interfere with the 2016 election. The president has repeatedly denied collusion.
"I don't officially start until the 15th Rob. But I just wanted to drop you a line to say if you ever need to pick my brains then my door is always open," Scaramucci wrote in the email. "Obviously there is still pressure on all sides, but if we remain consistent and united I don't envisage any issues we can't ride out."
Trump fired Scaramucci on July 31, not even two weeks after his appointment, after the financier gave a profanity-laced interview to the New Yorker magazine that he believed was off the record. Since then, Scaramucci has returned to SkyBridge as a co-managing partner while often defending Trump and his agenda in the media.
The source declined to explain the substance of Scaramucci's meetings with Goldstone. But when asked why Scaramucci interacted with Goldstone, the source said Goldstone "was helpful on the campaign." When asked to explain how Goldstone was helpful, the source said that the publicist was "just hanging around the campaign. Nothing specific."
CNBC asked Scaramucci to elaborate on his interactions with Goldstone, but he declined to comment.
The SkyBridge founder worked as a member of the Trump campaign's finance committee, helping it raise millions of dollars in the stunning effort that led to Trump's upset over Clinton. He had previously worked in finance roles on the failed campaigns of Wisconsin Gov. Scott Walker and former Florida Gov. Jeb Bush.
Scaramucci joined the Trump team in May 2016, the month before the Trump Tower meeting. He was not a participant in the gathering, according to published lists of attendees. In a statement to CNBC on Wednesday, he denied that his email to Goldstone had anything to do with Russia.
While it's unclear what Goldstone might have done to help the Trump campaign, the source said there could be more emails between Scaramucci and the British publicist that have not been made public.
Scaramucci was "hoping they released more" emails, the source said of the Senate Judiciary Committee's document dump. "The reason (he) would like to see (more) emails" is for context. It "had nothing to do with Russia," the source added.
The Trump campaign did not immediately respond to CNBC's request for comment.
The panel published hundreds of emails and other pieces of evidence among the 2,500 pages of findings from its yearlong investigation into the Trump Tower meeting. Some of the documents showed Donald Trump Jr.'s attorneys scrambling to get the participants in the meeting to follow the same message once the gathering became public.
One exhibit released Wednesday shows Goldstone forwarded an email from Trump Jr.'s attorney Alan Futerfas.
In the email, Goldstone is asked whether he is comfortable with how a statement about the Trump Tower meeting was written. The statement, in part, read: "As the person who arranged the meeting, I can definitely state that the statements I have read by Donald Trump Jr. are 100 percent accurate. The meeting was a complete waste of time …"
When Goldstone was asked during his private committee hearing whether he ever released the statement, he replied "no" and called it "ludicrous" because it seemed like "an across the board endorsement of Mr. Trump Jr."
Futerfas disputes that claim. He told CNBC that Goldstone had, in fact, cleared the statement with his team.
"Mr. Goldstone was advised that 'any statement should be accurate as to your very best recollection' to which Mr. Goldstone replied, 'Thanks looks good to me,'" Futerfas said.
Futerfas would not provide CNBC with the email that purportedly showed Goldstone corroborating what Trump Jr.'s attorney proposed at the time.
Goldstone's attorney did not return repeated requests for comment. Representatives for Senate Judiciary Chairman Chuck Grassley, R-Iowa, and ranking member Sen. Dianne Feinstein, D-Calif., also did not return calls for comment.
While details about Scaramucci's relationship with Goldstone were relatively scant, both the financier and Donald Trump Jr. have defended each other during recent controversies.
Scaramucci took to the airwaves to defend the eldest Trump son after former White House strategist and Trump campaign boss Steve Bannon ripped Trump Jr. in Michael Wolff's hotly debated tell-all about the administration, "Fire and Fury," which was published in January.
Bannon suggested the meeting, which also involved former Trump campaign chairman Paul Manafort and Trump son-in-law Jared Kushner, was "unpatriotic" and "treasonous." Bannon also said Trump Jr. would "crack like an egg" under the pressure of the Russia investigation, according to the book.
Scaramucci went on a media blitz to defend Trump Jr. as "a great American" while calling on Bannon to apologize.
Around the time "Fire and Fury" was published, Trump Jr., in turn, praised Scaramucci's scathing criticism of Bannon in the summer 2017 New Yorker interview that preceded his firing as White House communications director.
"The Mooch pretty much nailed it," Trump Jr. tweeted.