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When I first met Anthony Scaramucci nine years ago, he had a lot of questions for me: Where’d you grow up? Bella—are you Italian? Where’d you go to school? You’re not an asshole, right?
In fairness, he had questions for any journalists who wanted to talk to him in the weeks after his 2017 New Yorker interview helped end his 11-day tenure as the White House communications director under President Donald Trump. Since then, Scaramucci, 62, has become one of Trump’s loudest critics on social media, TV, podcasts and just about any medium you can name. The Mooch has done this while running SkyBridge Capital, the global investment firm he founded in 2005; hosting his Open Book podcast; releasing a book, All the Wrong Moves, in September; and still cheering for the New York Mets to not be a disaster.
Playboy caught up with Scaramucci to talk about the midterms, the art of “ratfucking,” the funniest thing that’s ever been said in the White House, and yes, Trump.
This interview has been edited and condensed for clarity.
Q1: The last time we talked, Anthony, was back in 2017 for Vice. The headline for that story was, “Anthony Scaramucci Has the Utmost Faith in Himself.” Where do you get that confidence from?
SCARAMUCCI: Maybe my mother or my grandmother. I tell my kids—this is a great line from Henry Ford: “Whether you think you can, or you think you can’t, you’re right.” So, you got to believe in yourself, and you got to push yourself. Self-skepticism is a path to disaster. It doesn’t mean I don’t get things wrong, but it just means that when you fail, forgive yourself and move on.
Q2: What do you think you learned from your parents while growing up in Long Island in the ’70s?
SCARAMUCCI: The number one thing, Tim, and I think you’re from an Italian family, but my mother and my grandmother were big-time Catholics. You had to do the right thing. Ash Wednesday was a big day in our family. You’re going back to dust, so don’t take yourself that seriously, and be nice to people because you’re only here visiting. But you got to do the right thing.
Q3: You were fired after your first year at Goldman Sachs. I know you were rehired shortly after that, but did you think that maybe you weren’t cut out for a life in finance?
SCARAMUCCI: Well, I had the wrong job. The big message from my first firing is I picked the job that I thought would impress my friends, but I actually sucked at it. I would have been better off picking a job that I liked and that I could have been good at. Goldman is a pretty tough place, and they realized what I realized: I did suck at the job, so they fired me. You also need to be nice to the people who are firing you. General [John] Kelly fired me from the White House, and him and I are very close personal friends.
Q4: I think a lot of people first came to you in 2010, when you told President Barack Obama on TV that Wall Street “felt like a piñata.” I know it got the attention of Jon Stewart back then, who called you “a Jersey Shore breakout star.” This was around the same time you were working on Mitt Romney’s presidential campaign, but when did you know that maybe you wanted to get more into politics, Anthony?
SCARAMUCCI: This is like a little bit of a Michael Corleone-The Godfather Part Three answer. I was honestly so stupid, and I thought I was in politics because it was helping me in business. I was a Republican. I was trying to raise money for them. It was leading to good business success. It’s when Trump won that I let my ego take over, and then I decided I wanted to go work for the president. That was my mistake.
I always tell people, “Don’t let your pride or your ego get in the way of your decision-making,” and that was me. I shouldn’t have done that. That was a terrible mistake. But like Michael Corleone, I’m in, and once you’re in, you can’t get out. You can pretend that you can, but you can’t get out. Every time you want to get out, you get pulled back in.
Q5: You first met Donald Trump in 1995, when you were at Goldman. You really got to know him better during those Romney fundraisers at his penthouse in 2012. What drew you to him back then?
SCARAMUCCI: Remember, I wasn’t drawn to him. I was drawn to [former Wisconsin Governor] Scott Walker and [former Florida Governor] Jeb Bush. I was drawn to rational Republicans. When Walker ran, I was close to him, and I said, “OK, I’m going to help him. If he doesn’t make it, I’ll go work with the Bushes again.” Neither of them made it, so Trump was actually my third choice. But I did something stupid. Jeb told me not to work for him. Jeb told me I was making a mistake working for him, and it would hurt me. I let my ego dictate what I was going to do, Tim.
I always tell people, “Don’t let your pride or your ego get in the way of your decision-making,” and that was me. I shouldn’t have done that. That was a terrible mistake. But like Michael Corleone, I’m in, and once you’re in, you can’t get out. You can pretend that you can, but you can’t get out. Every time you want to get out, you get pulled back in.
Q6: You wrote in your book how surprised you were when President Trump told you that you were going to be his communications director. I know much has been made of your tenure, but how did you approach that job when you were told, “You have no experience in this thing, but you’re going to do it anyway?”
SCARAMUCCI: I’ve done some really stupid things in my life. I’ll be the first one to admit that to you. That was, I think, at the top of the list, and it was an ego-based decision. I wasn’t experienced enough to be the communications director. It wasn’t the right job for me. Even though I gave, I think, a fairly decent press conference. Even though I understand how to communicate, I never had the experience … and that was all ego. That was me wanting to go work for the president. I built two successful hedge funds, I worked at Goldman and I had made a reasonable amount of money. I thought I was going to be able to help the public, but I also got subsumed by the idea of being inside the president’s inner circle, and it was costly. And I got my comeuppance.
Q7: The last time we spoke, it was only a couple months after the infamous interview with Ryan Lizza in The New Yorker. It was still so raw and fresh back then, but how have you processed what happened roughly nine years later?
SCARAMUCCI: I’ve been very open about how it was a big mistake in my life. I wish I hadn’t done it, but it did raise my profile. It did give me an opportunity to at least express my political views and my political philosophy. When you’re making mistakes of that magnitude, the biggest mistake you could make is not forgiving yourself. So, I said, “OK, I made this mistake. I have to forgive myself, and I have to go forward and not sit around and stew and play the victim.” It doesn’t work.
Q8: You wrote in your book that you didn’t understand Washington when you first got there. How do you make of it now? Do you think you understand it better?
SCARAMUCCI: I do understand it better. Washington is a weird place, a very cutthroat place. There’s a word called “ratfucking”—I can say that because it’s Playboy magazine (laughs)—and they go after each other and they ratfuck each other in ways that I could never imagine happening on Wall Street. These are very difficult, very mean people, and they go after each other with such a vengeance.
Washington is taking advantage of the Americans who are sitting around focused on their families and working, and Americans don’t understand all the games and the chicanery that goes on in Washington. But yes, I have a better understanding of how it works now, which is why those people hate me.
Q9: Most people will never understand what it’s like to be a topic for late-night hosts. You’ve been on both sides by now, as a target and then as a guest. What would you tell people about what it’s like to get roasted on late-night television?
SCARAMUCCI: I’m going to be brutally honest when I tell you that it sucks. If you’re playing in the National Football League and you’re a wide receiver, you have a 100-percent chance of getting a concussion. So when you get the concussion, like in my case in that stretch, you can’t complain about it.
Q10: You’ve been pretty open about what that experience did with your marriage to Deidre [Ball] and how you almost lost her. What did you both learn about yourselves as a couple and as a family when you were going through that?
SCARAMUCCI: I would just say that when you go through trouble and you really love somebody, and you have the fear that you’re going to lose somebody that you really love, if you’re able to repair it, you can come out a lot stronger. My friend Ben Stiller is a very famous guy. He had a falling out with his wife and they almost got divorced. They ended up living together during COVID, and then they realized, “Wait a minute, we actually really do love each other. What the hell are we doing getting a divorce?” They got together, and I think they’re stronger today than they ever have been. I’ve had that conversation with him, and I think that it’s a big message, frankly, to not make your relationships disposable. They repaired the relationship, and I think they’re stronger now than ever. I would say the same thing for me and Deidre.
Q11: I was reminded how you once accused Steve Bannon of “trying to suck his own cock…”
SCARAMUCCI: I said that he was in his office, sucking his own cock, which was one of the funniest fucking things that’s ever been said from the White House.
Q11: How do you think he’s doing today?
SCARAMUCCI: He’s doing as he should be. He’s a grotesque guy who is a hater, and he’s somebody that has done damage to the United States. I want the guy to rot. I think he’s a terrible human being.
Q12: I went back to the old interview that you did on Bill Maher’s show, when you addressed President Trump’s racist rhetoric toward “The Squad.” You’ve talked about how this was a real inflection point for you, in terms of your own moral and existential reckoning. What do you remember about that period in your life, when you started to speak out against this president you had been loyal to for years?
SCARAMUCCI: Listen, it was very hard for me because when I got fired, I didn’t want to be that baby. I tried to stay loyal to him. I was loyal to him for two years after I got fired, and then way back in 2019, I said, “This is ridiculous. He’s damaging the country, and he’s hurting us with his antics.” I didn’t expect the return of him. But I did say, “If you’re going to bring him back, he’s going to be 10 times worse when you bring him back.” And we brought him back, and he’s 10 times worse.
Q13: How do you think Trump has changed since your time with him?
SCARAMUCCI: I always say that I don’t think he has changed. I think he has been allowed to be something that he is, which is a complete asshole. And the old-school, more traditional Republicans would have blocked him, but in this case, these sycophants and these loyalists let him do whatever the hell he wants to do. He has effectively destroyed the Republican Party.
Q14: A lot of people know you in the politics space, but SkyBridge Capital and the SALT Conference have done well in the world of finance. How can people who are struggling in this economy make smart investments and build a portfolio?
SCARAMUCCI: First of all, my heart goes out to these people because remember, I started out in a very humble way. I think that we have to try our hardest to save each month. Even if it’s just $50, we have to try to put it away. For me, I would just tell people that monthly, quarterly, semi-annual savings will add up. You pay the cable bill, you pay the electric bill, you pay the car payment. Find $10, $20, $50, and try to pay yourself. If you do that, I think you’ll end up being very, very rewarded.
Q15: You’ve been pretty big on Bitcoin, saying you fundamentally believe that this is a technological shift in finance, and that “this asset should be worth $20 trillion.” What is it that people are still missing when it comes to Bitcoin and its role in the future of finance?
SCARAMUCCI: Rightly or wrongly, I’m a huge believer in technology. The technology is going to be deployed, and it’s going to make things cheaper. We’re going to have greater security. I made the investment seven years ago in Bitcoin, and I did not anticipate the regulatory resistance, the headwind of tokenizing assets or getting markets to trade 24/7. I’m surprised that it’s taken this long, but it’s going to be used. One axiom that I have found in my life: “If you have better technology, the technology gets adopted.”
Washington is a weird place, a very cutthroat place. There’s a word called “ratfucking”—I can say that because it’s Playboy magazine—and they go after each other and they ratfuck each other in ways that I could never imagine happening on Wall Street.
Q16: Records are meant to be broken, but I don’t think anyone anticipated Katie Zacharia smashing your record …
SCARAMUCCI: She knocked me out of the Guinness Book of World Records!
Q16: You had said that the universe had done her a favor, but what what would you tell her about life after a very short tenure with the Trump White House?
SCARAMUCCI: First of all, I like her. I had the opportunity to meet her for the first time on Piers Morgan’s show, where I did a did a television segment with her. I just said, “Katie, relax. You’ve got a great life, you’ve got a great family, and enjoy it.” Don’t take the screeds or the attacks or the comedians too seriously.
Q17: We’re talking three days after the “blue tsunami” happened in the midterms. You’ve tweeted about how this is the end of MAGA, and you recently said the Republican Party was heading into a civil war in these next two years. Why do you think that is and what would it look like?
SCARAMUCCI: I don’t know what it’s going to look like, I have to be honest. But I definitely think we’re heading into a civil war, and I definitely think that there’s going to be traditional Republicans that are going to be fighting for the future. If you are Trump-adjacent, you’re going to have very hard time winning the presidential nomination. He sucks. His popularity is at an all-time low. You’re tainted by him. Every one of these people have orange Cheeto stains on their hands and their lips from kissing his ass. I don’t.
I think it’s going to be very hard to come back from that and pretend you weren’t with him. What are you gonna do? You gonna burn your MAGA hat now? There are just too many receipts.
Q18: In September, President Trump promised $5,000 checks to every American adult if Republicans won both the House and the Senate in the midterms. Were you looking forward to getting that check, and what would you have spent it on?
SCARAMUCCI: I don’t know if you saw, but I said [on X], “It looks like I’m not going to get my check.” That got a lot of retweets. That was really fucking funny. Of course, I would have spent that. I would probably bought myself some fucking champagne.
Q19: How would you describe your approach to social media, especially on X? Because it feels like the Mooch persona is a very online character now.
SCARAMUCCI: I like going on X and I like going on social media because I feel like when you go into politics, your adversaries try to characterize you and they try to make you two-dimensional. But social media gives you the opportunity to provide your own voice, and it provides you the opportunity to be three-dimensional. They’re able to see me for who I actually am, as opposed to the way somebody wants to portray me.
Q20: You have said you could be richer if you were ruthless, but you prefer being nice, and that niceness is your superpower. Why is that?
SCARAMUCCI: Li Ka-shing, the property magnate, he said to me 30 years ago, “Leave money on the table for your partners, because what will happen is they’ll always want to do business with you. If you’re going for the last dollar, you’ll probably get it, but then you’ll be miserable because you didn’t ask for $2.” Now, my attitude is, “I want to do business with people. I want them to like me. I want to like them. I don’t need to be a ruthless prick.” The Mets doubled the price of my suite at Citi Field. I was a 26-year suite holder, and I said, “OK, if that’s how you guys are going to treat your loyal suite holders, take the suite back.” I just bought myself a Legends Suite at Yankee Stadium, no problem.
My point is I want to be nice to people and I want to be treated fairly. You want to treat me differently, then we move on. It’s not a big deal, but I think it’s a superpower because you’re a happier person when you treat people with respect and kindness. It comes back to you, Tim. You’re a happier person. I may not be the richest person, but I’m living a good life.
