Anthony Scaramucci On Trump, Getting Fired From The White House & Failed Marriage

I was in a pretty abusive domestic situation as a kid. I had done everything right to get the most coveted job, except I was not interested in the job and I sucked at the job. When you say '80s on Wall Street and I got there in the late '80s, early '90s, I'm thinking cocaine and booze. But go ahead, let me take you through my day on the 31st of July. Okay. I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late-night comedians.

I mean, it's a pretty generous introduction. [laughter] You know, I feel generous when I think of you. Oh, well, thank you. You've got me through some tough times, most notably the last US election. [laughter] It's been a tough time. I mean, it's interesting. You know, it's a decade now where Trump has loomed over the political landscape. Um, and weirdly, that four-year interregnum period made him more malicious, more malevolent, and sort of he's like, "Hey man, I didn't steal enough in the first term." He had four years to figure out how to steal more. So, it's been difficult. I mean, and we got two-plus years to go.

I'm too short to see the glass anything other than half full. I mean, just so everybody knows, before this podcast started, they told me to sit up. So, I was trying to sit up, but my legs are dangling like Shrek from, you know, the first prince in the Shrek movie.

No, very much so. No. No, I wasn't born like that. I think that's interesting. I come from a family of blue-collar pessimists. I find that, like, the neighborhood I grew up in, everybody, you know, everybody's decided that the universe is against them. And so you have to train yourself to think in the opposite direction. So, actually it's 35 years old now, but I read a book called Learned Optimism when I was in my early 20s. It was written by a psychologist by the name of Martin Seligman. And I remember I was in school and I said, okay, this is the antithesis of the way my family thinks. I have to force myself to think in this optimistic way. And so I became an optimist through training, but I didn't start out as an optimist.

I don't now. I don't have to practice. In fact, I talk to younger people about the word pronoia. Do you know this word?

It is. Okay. Yeah. P-R-O-N-O-I-A. You have to believe that about the universe. You have to believe that the universe is bending towards you in your life. When you do that, even when really bad things happen to you, you can see the bright side to it.

Exactly. Yes. I mean, you know, it's fine.

Yeah. I mean, well, listen, you have two choices when you fail. You can slink away and hide. You can pretend that it didn't happen. You could lack accountability. You can play the victim. You can blame others. I can give you the whole list of things that you can do. Which is, I think, the greatness of your podcast because I think what you're trying to tell people, and it's really good in the UK culture for people to feel this way: it's okay to fail. There's no shame in it. Where the shame comes in is if you're not honest with yourself because what'll end up happening is you'll dig yourself a hole that you can't get out of. You know, imagine if I had failed from the White House and then just slinked away and then was dreaded by that for the rest of my life. You know, I mean, the coin of failure is tied to forgiveness. And so when you're flipping that coin and you see it land on failure, flip it over. You have to forgive your failures. If you don't do that, that's a mistake in life. Life's too short not to forgive your own failures.

You just need to think about it that way, though. You know, remember, you know, if you grow up Christian, I was raised as a Roman Catholic, they teach you about redemption and forgiveness. But how about forgiving yourself? I don't walk around with a millstone of regret on my neck every morning. I don't kick myself in the pants every morning. Say, "Geez, I made a terrible decision to go work for Donald Trump. Let me kick myself in the pants this morning." You know, you got to let that go and you got to focus on today and tomorrow.

I mean, that's probably the... I mean, listen, I was a little bit of a renegade and a rogue in high school. So one of my teachers said that I would try to put a gallon of water in a one-quart bottle, which I guess he thought I only had one quart of capacity, but it meant I would try to do too much in my life, which I've certainly tried to do that. You know, I would say in response to that, because I did read that, I would say I was definitely a character in high school, but I was a wayward character. I was hanging out. I was trying to socialize with women. I bought myself a used Camaro. I was sort of like an Italian Guido out cruising on Long Island, if we're really going to be honest. My role model was like Tony Montana from Scarface. How bad is that, right? I mean, I had the gold chains. I had my hair slicked back like John Travolta in the movie. I was believing too much of my own BS, you know? And I didn't get straightened out until my senior year in high school. When I look back on that, there was a gross period of immaturity, actually.

You know, my parents actually. You know, my father was like sort of the strong, silent, working-class type. I mean, he was a strict disciplinarian. I mean, he used to beat the daylights out of us, but that was customary back in that day. But he was a loving guy and he wanted us to do well. He wanted us to go to college. He didn't have the money for the schools that I went to. And so I had gotten into Tufts University, which I don't know if it's a well-known school here in the United Kingdom, but it was a, you know, it's probably like a top-25 private school in the US. And I had gotten into the state school, which is a good school, but it was up in Binghamton, New York. It was sort of a remote area. Tufts is like right in Boston next to Harvard University. And my guidance counselor went to see my father and my mother, and Elizabeth, they were smoking cigarellas, just to set the scene for you. And we had this little tiny circular table just right off the hallway kitchen. And my mother was pouring the espresso and it was coming out of this cast-iron pot like motor oil. Okay, it's like 8:00 at night. They're smoking cigarellas and drinking espresso that is like six times the caffeine of anything you'd find at a Starbucks. I mean, these people, I don't know how their hearts didn't explode. And John Zanetti, in Italian, spoke to my... it was actually a dialect of Italian, a southern dialect. They were all from that area, and he told my father, "You got to have Anthony go to the private school, have him go to Tufts." My father thought it was spelled like T-O-U-G-H-S. He literally had no clue. But the very next day he told me he was cashing in his life insurance policy from his union and he gave me a $10,000 check. Probably two weeks later, he handed me the check and he said, "Okay, you're going to go to Tufts. I don't really have the money for it. I cashed in my life insurance, got the cash value for it to help you get started." And I think that scared me straight. I thought that the love to do that and then the sacrifice and then the pressure. I was like, "Okay, I don't want to let my dad down. I got to make sure I study." So, I like literally dropped the Camaro. I bought myself a Nissan Sentra, which is like not a flashy car at all, and I went to school, and I got very good grades at Tufts and good enough grades to get myself into Harvard Law School.

Yeah, it paid off for my old man. I used to always tease him. He passed away in 2023. I said, you know, that $10,000 cashier's check from your life insurance paid off for you. I used to tease him.

No. No. So, I started the podcast in April of '24, but you know, look, he got to see the ups and downs of my political career, the ups and downs of my Wall Street career. And, you know, for my parents, you have to remember the bar was low. I mean, all they wanted us to do was go to college, you know. I mean, the funny part about my mother is my mother wanted me to be a lawyer. So, I went to Harvard Law School, but I never practiced law. And she used to lie to her blue-collar friends in the neighborhood. I was in Rosano's deli ordering myself like a, you know, big salami sandwich and I'm standing there next to Mrs. Cazenza, who's my mother's best friend, and she's like, "How is that law firm, Goldman and Sachs? How is that law firm?" I'm like, "What?" She goes, "Your mother told me you're working as a lawyer at Goldman and Sachs." I'm like, "She did?" She says, "Yes." I said, "It's, Mrs. Cazenza, it's great." And I'm like, I call my mother. I'm like, "Why are you lying to your friends? I'm embarrassed for you that you're this investment banker. I don't even know what that is." That's amazing. That's, you know, that was the neighborhood I grew up in. I mean, no one knew anything. They didn't know the difference between Goldman Sachs and... you picked the law firm.

First thing that came to mind for this book, and I had the idea for it a few years ago, but there are so many people... like I travel the country. I do a lot of public speaking. This is even before the podcast. So, you know, from the notoriety of getting fired from the White House, I do public speeches, corporate speeches, how to build yourself back up. There was a lot of resilience speeches, different things like that. And when I would travel the country, I would be astonished at the following rhetorical question: How did we get here? What happened to this country where we have this morose tribalism? We have this anger-based populism. What actually happened to the country? And so, this is a reflection on my 38-year Wall Street career. This is some input from my failure as a White House communications director for Donald Trump, but also my observation as a political fundraiser for three decades for the Republican Party. And then it's also a little bit about my upbringing because I did grow up in a blue-collar neighborhood where my parents had bought a house, thank God, they paid $16,000 for it in 1962. And we had a good upbringing. I would never dishonor my dad or my father's work ethic by telling I grew up poor. Did not grow up poor. But, you know, we had a tight budget and things were... we had to be disciplined about what we were buying and things like that. So I had that perspective and then I was able to go to Goldman Sachs and build some measure of wealth and then I created a couple of successful hedge fund businesses and so, you know, I reached a financial independent status, if you will, and so that class movement in the United States I think has given me a perspective on the country where I can tell you about the divide. I can tell you about the pain that's in the divide. And I can tell you how I think it happened and then what we could potentially do to fix it.

Yeah. So, it's not a law firm, by the way. It's actually a high-profile investment bank. I mean, Mrs. Cazenza. I mean, I don't know why. My mother, my mother. I mean, come on.

I didn't. And so, I mean, that was one of my failures actually, which wasn't one of the big three that we're going to mention here, but I failed the bar exam after law school. Okay.

Yeah. Yeah. Well, like John F. Kennedy Jr. too. Remember, he failed it a few times, but I failed the bar because I was going to Goldman, and this is how arrogant and how smug I was, because I had never failed anything. I figured I didn't have to study for it, but that test is actually designed for you to have to study for it. And so I failed the bar coming out of law school, out of Harvard Law School, no less. And my mother was super upset about that. And so I went back and took it and passed it, okay, to appease her, but also I think it was another big message in my mind: you got to be a finisher in life, you know. So even though I didn't practice law, I went on to pass the bar. So that was a minor failure and that was due to smugness and arrogance, frankly, and it was a bad, bad idea all around. But anyway, back to getting fired from Goldman. This is like the best and the worst story. So I went to Goldman Sachs, Elizabeth, because it was the coolest job at the time. So just hear me out. I'm a 25-year-old insecure kid from not even the outer boroughs of New York. I'm from a working-class family on Long Island. I've gotten to Harvard Law School. So, I got to prove to people that I'm the coolest. So, how do you do that? Well, you got to get the coolest job. Okay. So, what the coolest job was at that time was real estate investment banking because the real estate industry was super hot and so was investment banking. So, if you combine the two of those, that was the hottest job. It was the most coveted job from the Harvard Business School and from the Harvard Law School the year I graduated. So, I was hell-bent on getting that job. The problem with that was I absolutely sucked at that job. I was ill-suited for it. I had to be trained. I mean, I was able to convince the people to hire me. And I always tell younger people that you got to pick a job in life that you really like, that you're driven by, that you have passion for. Don't pick a job where you're trying to impress your friends or you're trying to grab onto some status or a totem of status, which is a false promise to yourself. So this is an important lesson in failure because I had done everything right to get the most coveted job except I was not interested in the job and I sucked at the job. Okay. So I'm hired and start my work on the 14th of August 1989 and on February 1st 1991, you can look it up, it was a Friday night. I remember it like it was yesterday. My boss sat me down in his apartment in Greenwich Village. Invited me over for a beer and I went over to his house to have a beer and he fired me and they were downsizing because of the Gulf War and they were in the beginning of a recession and he said something to me. These were immortal words that are burnt into my brains. I'll share them with you. He goes, "You know, you're a great guy. You're a very hard worker. You're a disciplined guy. You absolutely suck at this job. Okay, this is the wrong job for you and so I'm firing you. I'm letting you go and here's your $11,000 severance check and we're going to give you one week in our career resources place to build a resume and make some phone calls and stuff like that, but you're fired." I don't know why and I don't know how I did this at that moment, but I said to him, I said, "Mike, can I use you as a reference?" I said, "It's got to be hard for you to fire me." He had fired like 20 people that day. He looked exhausted and I was thinking he fired... it was 8:00 at night. And I said, "I just, you know, you said I had a good work ethic and stuff like that. If I'm in the right job, can I call you for a reference?" And he said, "Okay, absolutely, no problem." And he said as much. And so I went home and I was like, what am I going to do? I'm 27. I went to Harvard Law School. I've been fired from Goldman Sachs after 18 months. What am I going to do? I went to the bank. I got three rolls of quarters. Why did I do that? Remember this is before cell phones and it was 25 cents to make a payphone call. And I got three rolls of quarters and I was living outside of New York City. I took the train back into the city, was in Grand Central Station, Elizabeth, and I was pumping quarters into payphones to call people. I had a stack of resumes that I had printed out and I was going to go look for a job. And I got on the phone with somebody and he said to me, "Listen, there's a job at Goldman Sachs in the sales and trading area. They've had a couple of people leave recently. You should try to get that job." Oh, next phone call was to Mike Vasetelli, the guy that fired me. I'm still very close friends with him, by the way. And I said, "Michael," I said, "There's a job on the 20th..." I was fired on the 10th floor. I said, "There's a job on the 29th floor. I think I'd be good at that job." He said, "You know, I think you actually would be good at that job." He went up to see the partner in charge of that area. And then he called me and he said, "Okay, they're going to interview you tomorrow at XYZ time." And I got rehired into Goldman. Okay, so I got fired on February 1st. On March 26, I got rehired into Goldman. And then the personnel department called me and they were like, "Hey, you know, we're going to mark you down as an interdepartmental transfer. We're never going to have to tell anybody you got fired. Can we get the $11,000 check back?" Elizabeth, I was like, "Actually, you can't. Actually, I've already spent it. You know, I spent it on some of my school debt. I bought some suits for these interviews." I said, "Yeah, you can't get the money back." I said, "No problem. You know, you can tell everybody in the world that I got fired. I don't care." She was great, by the way. She marked me down as an interdepartmental transfer anyway. She just retired from Goldman actually, 40 years at Goldman. She was in their personnel department.

Oh, yeah. Well, the number one thing you do is you blame everybody else but yourself. And then in the process of blaming everybody else, you burn all the bridges. That was Mike Vasetelli's fault I got fired, not me. I didn't do anything wrong. See what I mean?

But I don't know what it was. It was either instinct. I hadn't thought it out as carefully as I have today, 30 years after my firing or 35 years after my firing. But I definitely would implore people that when bad things are happening to you, take a step back, take a deep breath, and get into a channel inside your brain. Okay? That is the adult channel. Okay, there's almost like a, you know, like a psychotherapist would say, a witness mind. The witness mind is when you step out of yourself and you're observing yourself as a third party and then start acting in a very rational way. Don't let your emotions run the program for you.

Well, I'm Italian. I mean, so I mean, you know what Italian Alzheimer's is?

We forget everything but the grudges. I mean, you know, we could be very vindictive and very vengeful. You know, you know what I'm talking about, right? Come on. You've seen enough Godfather movies. We get super wickedly pissed, right? You know, first of all, you have to understand those instincts and then you have to hit the override switch. Okay. And it's like you ask me something about being a pessimist. So, I am an optimist today. I mean, I've trained my brain to be optimistic. I didn't start that way any more than I started without having, you know, that like vengeance or anger-based vendetta and all that sort of stuff. You got to... not saying it doesn't exist, but you have to like do something transformational to overcome that and to make your responses at a higher human level. You know, that's lower-level thinking for a human being. Higher-level thinking is the process of forgiveness. Forgiveness of others, forgiving yourself, and pushing yourself into a more sublime position as a human being. You're capable of doing it.

Lots of drugs. Lots of drugs.

I actually didn't, by the way. And thank God I didn't because I come from like a family of drug addicts and alcoholics and so I'm, you know, again, gambling addicts, drug addicts and alcoholics. So I made a decision at a very early age to avoid all of that stuff because I wanted to move from where I was. I looked at my family situation. I said, "Okay, if I do what every single person in this family is doing, I'm going to end up like every single person in this family. So I got to switch it up. I've got to think about it creatively and think about it alternatively." So I actually didn't do it. But when you say '80s on Wall Street and I got there in the late '80s, early '90s, I'm thinking cocaine and booze, but go ahead.

The Bonfire of the Vanities. Yeah, it's very well written. Sherman McCoy. Yeah.

Well, I would say like The Godfather, art imitates life and life imitates art. And so like the mobsters watched The Godfather, then they became like the mobsters in The Godfather who were observing the mobsters who weren't in The Godfather to create the mobsters. I mean, I just said like a weird syllogism, but you get the point that I'm making. And so after The Bonfire of the Vanities came out, it became like an anti-hero novel but people started to adopt the suspenders and the mannerisms of the people inside the book, you know, the social X-rays and the people getting super thin and all the different things started happening. Moreover, when Oliver Stone wrote and produced Wall Street, which was late late '80s, I think Bonfire of the Vanities was like '86 or '87. Oliver's movie came out in December of '87. The anti-hero Gordon Gekko, Michael Douglas, I was in Wall Street 2. I had a role in Wall Street 2. I got close to Michael Douglas and Josh Brolin and Shia LaBeouf. Michael told me that Wall Streeters would come up to him in New York City restaurants and say, "Hey, you know, it's because of you I came to Wall Street." And Michael would be thinking to himself, you know, I was like the insider-trader bad guy that went to jail. Did you not remember that part of the movie? You know what I mean?

"Lunch is for wimps." All of the stuff that he said in that movie.

It's very nice to have money. There's no question about it. It's better than not having money, but like also with money does come some level of responsibility. So again, I'm from a blue-collar neighborhood. So I have family members that are not doing well. Okay? So, if I have a family member that's been disabled because of hard labor, well, guess what I'm doing is I'm subsidizing their life. So, I want them to be okay. You know, I've paid for cars, health insurance, college tuition, master's degrees. You know, I have to because these are people that I grew up with. You know, my mentor is a guy named Bob Cascarano and I acknowledge him in the book and you may remember Ken Langone. I don't know if you would recognize the name, but if you're in New York, Kenny gave $200 million to NYU. It's now called the Langone Medical Center, and then he gave like $2 billion to the endowment so that if you get into medical school there, you can go for free. So, he's one of my elder statesman mentors. He just turned 90 last year. Those two guys would say to me, and they would say to you, Elizabeth, "Hey, man, if you made it from a blue-collar neighborhood and a blue-collar family, help the people." Okay. And remember, the country does better when we put a hand out to reach up to somebody and pull them up. You follow what I'm saying? And so when you say, "Is it nice to have money?" It is very nice to have money. I mean, I have like modest houses, but I do have houses. I don't have one house because I don't want to live in this gigantic house because I think there's a paradox to wealth. And I'm happy to explain that to you if you want my theory on it. But I love cars, you know, because my uncle was a... I grew up in a motorcycle shop and so we always had cars around. And so when I was a kid manifesting my life, I'm like, "Okay, if I ever get rich enough, I'm going to own a Rolls. I'm going to own a Lambo." I mean, I'm a little bit of a nouveau Italian. What the hell you want from me? I mean, that's what it is, right? So, but I don't live in these big fancy pants houses because I think it's really bad for my kids. I want my kids to be able to cross the street, ring the doorbell next door, and go play with the other kids in a neighborhood. There's a paradox to the wealth. So if you become very wealthy and then you got to show off your wealth, what are you going to do? You're going to buy a big mansion. Okay, that's great. Now you got a 15-acre estate. Oh, that's great. Now your kids are sitting alone in the mansion. Oh, wait a minute. I'm super wealthy. Let me go fly around privately. Okay, now the kids don't see an airport. Oh, I go on the Disney cruise. You know, Kady thinks I'm crazy. She hates Disney. But I go on the Disney... I want my kids to socialize with these other kids on the Disney cruise. You see what I mean? Yeah. If you're not careful, your wealth will make you very depressed and very lonely. It's almost like a... it's almost like a sociological trap. I don't know, maybe it's God or the universe playing a trick on you. Okay, you wanted to get the wealth and then the wealth becomes a Faustian bargain with the society if you're not careful with it. So, I try to use my money for charity and help people. I do have a couple nice things. I'm not going to say that I don't because I do and I like nice things and it's convenient to have access to medical care and things like that, but I'm trying to help the people around me with it.

Oh, no more Nissan. Oh, yeah. Nissan. We had a linguistic...

Yeah. And my ex-wife will probably be mad at me for talking about it so publicly, but I did all the wrong things in my marriage actually. And you know, like this book is called All the Wrong Moves. If I was going to write a book about my shortcomings or my failures, it would have been a phone book. Okay. My first wife and I got married at 24. That was me and she was 25, respectively. We met in college. And we had a very good relationship in the beginning, but some of the problems that I had as a kid, I brought into my marriage. And so, what were those problems? Well, my dad was a very strict disciplinarian. I mean, he used to beat the daylights out of us. And he was a temperamental guy. And so, you can replicate that, right? Psychologically, you can downward shift into that and you could become that, okay? Which often does happen in situations where there's alcohol and there's other things going on in a family, or you can try not to do that, right? And so, but what you got to be very careful of is you create this antipodal effect where you go to the other extreme. Okay, so here's the self-narration. Okay, you ready? Yes. I was in a pretty abusive domestic situation as a kid, so therefore I am not going to be abusive and therefore I'm going to be a conflict avoider. And so therefore, you and I are in a relationship and you're doing things that I don't like. I'm not going to tell you about them because I fear conflict so much that I'm not going to be able to express to you what the things are that are going on that are wrong in the relationship for me.

Okay. And so then what happens is you have this crazy job. So, you mentioned the money, but you have to remember the money for me came with ridiculous amounts of work and it came with W-2 income. So, what does that mean? Let's say if I made a million dollars, I live in the city and state of New York, I'm getting taxed 52% of it. I get to keep 48% of the money. And so, you have to work off of the 48% of the money in each year in succession. And so I was working around the clock when I started my own business, which is... it's better if you can be successful in your own business in the United States, you'll make more money, but think about all the problems that you have in your business. And so now, was I neglectful to my marriage in that process? I 100% was. And it cost intimacy, it cost relatability. And then the conflict-avoiding, which was a terrible part of my personality. And I would recommend to people, if you're in a problem situation in your marriage or things are not going right, you have to face the music with yourself first to figure out what it is, right? It's never 100-0. I mean, people can pretend, you know, "We got divorced, she was 100% wrong, and I was 100% right and it was 100-0." We could pretend that, but it's never that. You know, there's culpability on both sides. And so, I didn't face those demons in my personality and I...

didn't face, how can I say this? The m, you know, you're, you have your nature. You're born a certain way. You're born a certain way. I'm born a certain way. But then you have your nurture and that's affecting your personality is affecting the operating system of how you think. And I was so concerned about conflict and the way I was treated as a kid that I was never going to do that to anybody. But then that puts you too far away from the base standard of what is appropriate to say. You know, Elizabeth, we have a relationship. Here's things that are going right in it. Here's the things that are going wrong in it for me. And by the way, you may have some things like that, too. We love each other. Let's try to figure it out. I didn't do that. And so, that is a big epic fail on my part. And I don't have anybody to blame other than than myself. Our marriage ended up fizzling probably a decade before it actually ended. And we were both Roman Catholic. So we didn't get a divorce right away because something about the church, you know, we try to stay married even though your marriage isn't working. Someone will have to explain that one to me in a different life. But in the Catholic, you know, the sacrament of marriage, but we we were better off apart than we were together. But the way we ended it is uh something I really regret because I didn't have the fortitude to handle it as directly as I am right now. But by the way, I will also say this. My second marriage almost ended in divorce as a result of my White House career. We'll get to that one. But I think the learning, the self-learning and the self-edification of what went wrong in my first marriage helped me resolve whatever things that were going wrong on my second marriage. You're married once,