Filling the shoes of press secretary and acting White House communications director Sean Spicer, who achieved iconic status when played by Melissa McCarthy on Saturday Night Live, would present a tough task for anyone. But former hedge fund founder and enthusiastic Trump defender Anthony Scaramucci has eagerly taken up the job.

The position of White House communications director is an important one, responsible for delivering the administration’s message, which has been a difficult (if not impossible) task during this scandal-riddled presidency. Spicer was initially appointed to the role of press secretary, and then also given the director of communications title, but he was rumored to be on his way out after months of humiliations and increasing invisibility. He announced his resignation on Friday following Trump’s appointment of Scaramucci.

Scaramucci is a Wall Street executive who earned a track record for coming to the vociferous defense of Donald Trump on Fox News. In defense of Trump’s frequently false statements, Scaramucci famously told MSNBC, “Take Donald Trump seriously but not literally — or better yet, take him symbolically.” He certainly knows how to get the president’s attention, addressing Trump personally during one of his first TV appearances in his new role on CNN’s State of the Union on Sunday.

Here are five things to know about Scaramucci, or “the Mooch,” as he is known in the finance world.

1) This is at least the fourth job Scaramucci was offered by the Trump administration

Scaramucci first served on the executive committee for Trump’s transition team. In January, he was set to join Trump's White House staff as an adviser and public liaison to government agencies and businesses, but that position was later retracted after concerns of conflicts of interest. In June, he joined the US Export-Import Bank as senior vice president and chief strategy officer, according to Politico.

2) He has no communications experience

Scaramucci started his career at Goldman Sachs, and then in 2005 he started his own hedge fund, SkyBridge Capital. At no point has he filled any positions in communications-related jobs.

So why would Trump hire Scaramucci for the communications director position? According to an anonymous source quoted by the Washington Examiner, “Scaramucci would take the prestigious communications director title ‘but would not be fulfilling that responsibility because he doesn't know how,’ the source said”:

"Basically, Trump wanted to give Scaramucci something to do because he thinks he's a 'good Italian kid'," the source said, noting that the decision to hire Scaramucci was based partly on the Trump supporter's performance defending the president on television.

In the July 21 press briefing, Scaramucci insisted he has communications experience because he was a successful entrepreneur: “I think that you will find in my background and in my career, I have a lot of communications experience and I spent a lot of time on television. I spent a lot of time shaping the message of my old firm.”

3) Scaramucci is the founder of SkyBridge and its infamous SALT Conference

SkyBridge is a hedge fund that works with wealthy Americans — who are not super wealthy. In the words of New York magazine’s Jessica Pressler, who profiled Scaramucci and SkyBridge in 2012:

Hedge funds are traditionally the province of the superrich, but Scaramucci aims to make SkyBridge — a “fund of funds” that creates portfolios of hedge-fund investments — the first company of its kind to target “the mass affluent.” That is, investors who have the $200,000 annual income or $1 million in net worth the SEC requires of “accredited investors” but aren’t connected enough to get in with a Daniel Loeb or a John Paulson.

Every year, Scaramucci hosts the SkyBridge Alternatives, or “SALT,” Conference in Las Vegas. Pressler described the “hedge-fund bacchanal” in 2012 as being “launched in 2009, in defiance of former President Barack Obama’s warning Wall Street to stay away from partying while the rest of the country suffered.”

SkyBridge, beyond the conference, has its critics. Pressler spoke to Felix Salmon, then at Reuters, about covering Scaramucci, whose techniques to win investors Salmon called “sleazy” and “dangerous”:

“He is putting people into hedge funds that really shouldn’t be invested in hedge funds,” says Salmon. “He has this extremely expensive smile and very good hair, and they trust him. And to the degree that he’s accomplishing it, he’s hurting America.”

4) Scaramucci was the subject of a retracted CNN story that the Trump points to as evidence that the Russia story is “fake news”

On June 22, CNN published a story citing an anonymous source that linked Scaramucci to a $10 billion Russian investment fund. The network later retracted the story, saying it did not meet CNN’s editorial standards, and the three CNN employees who were responsible for the story subsequently resigned. However, CNN has not directly said the story is entirely false.

Scaramucci tweeted in response to the story:

.@CNN did the right thing. Classy move. Apology accepted. Everyone makes mistakes. Moving on. https://t.co/lyVajCKNHx — Anthony Scaramucci (@Scaramucci) June 24, 2017

President Trump, however, reportedly did not move on. According to Politico, he was impressed that Scaramucci received a retraction from the network that Trump himself frequently derides as “fake news.” (The president recently retweeted a video that showed him beating up a man whose face was covered by a CNN logo. Vox’s Aja Romano wrote an explainer on that controversy.)

5) Scaramucci hasn’t always been loyal to Trump

In 2012, Scaramucci appeared to be a big Hillary Clinton fan. In tweets resurfaced by the Daily Beast but since deleted, Scaramucci tweeted, “I hope she runs [in 2016], she is incredibly competent.”

According to the Daily Beast, Scaramucci deleted his tweets critical of Trump and supportive of Clinton hours after accepting the position as communications director.

Scaramucci ultimately endorsed Scott Walker and then Jeb Bush for the 2016 presidential election. While supporting Bush, he spoke critically of Trump, saying in 2015 on Fox Business Network that Trump is an “anti-American hack”:

I’ll tell you who he’s going to be president of — and you can tell Donald I said this: The Queens County bullies’ association. You gotta cut it out now and stop all this crazy rhetoric, spinning everybody’s head. I don’t like the way he talks about women. I don’t like the way he talks about our friend Megyn Kelly. And you know what? The politicians don’t want to go at Trump because he’s got a big mouth and he’s afraid he’s going to light ’em up on Fox and other places, but I’m not a politician. Bring it.

In the first press briefing since Scaramucci’s hiring, held on Friday afternoon, he took questions from the podium, including one about how he had once called Trump a “hack politician.” Scaramucci, it seems, is still repenting for his sins:

Oh, my god, he brings it up every 15 seconds, okay? One of the biggest mistakes that I made is that I was an unexperienced person in the world of politics, I was quoting another candidate, I should have never said that about him, so Mr. President if you are listening I personally apologize for the 50th time for saying that.

But beyond his loyalty to Trump, some are scratching their heads over how long he’s been involved in the Republican Party. In 2012, he tweeted in favor of increased gun control in the US.