O'REILLY So here we are on Do It Live, all right, again. And I got a very special guest, Sid Rosenberg. Now, for those of you who don't live in the New York area, and remember, 16 million people do, okay? Rosenberg is a top talk guy on radio for everybody. He just wipes them out month after month after month. But here's the kicker on Rosenberg, he should be dead. All right, he shouldn't be the top of anything. He should be in the ground and somehow survived madness and then climbed to a very, very difficult position. I mean, to be number one in the nation's largest market is a very, very steep accomplishment. So, all right, Rosenberg, I've been nice to you. That's gonna end right now. The national audience may know you from Crazy Imus. 

ROSENBERG That's right. 

O’REILLY That's where I want to start. So, Imus selects you as his sports guy. 

ROSENBERG How it worked was, Imus had a boss, and his name was Mark Chernoff. Well, Imus didn't really have a boss. But Mark Chernov was the boss at WFAN. And I had just done a year at a station called WNEW in New York in the year 2000, doing a sports show, my first year coming out of Florida, and it was awful. The ratings were terrible. Quite frankly, I was terrible, but I guess I did enough to impress the powers that be at WFAN. So after WNEW in 2001 decided not to bring me back, I was heading back to Florida. But I was told by somebody at the fan, hey, before you go back, do yourself a favor. Call Lee Davis, he was the guy in charge of sales. Call Mark Chernoff, they like you. I said, they liked me? This was the worst show in the history of radio. 

O'REILLY And no one likes you. 

ROSENBERG And no one likes me. And they liked me less back then. But long story short, Steve Cohen was his name. He ran the sports at Sirius XM for about 20 years, not the Cohen who owns the Mets. And he was right, they like me. So Chernoff is a guy who went to Imus, who, at the time, was using guys named Mike Breen, you may have heard of him, and Warner Wolf, and John Minko. 

O'REILLY And he fired Warner Wolf, right? 

ROSENBERG He did fire Warner Wolf twice in favor of me, but this time in early 2001, Chernoff said, I got you a sports guy, and Imus said, I don't want him. And Chernoff said, you're gonna try him, he's good. So he was reluctant to bring me on, Imus, but it turned out to be a hateful, loving 18-year relationship. 

O'REILLY Okay, you were on that show 18 years, that's amazing. And Bernard McGuirk, the late Bernard McGuirk, who I used on The O'Reilly Factor, Gutfeld, and McGuirk. I made Gutfeld, by the way, and I regret it. 

ROSENBERG It was Tuesday nights, I remember that vividly, it was great. 

O'REILLY You're walking into the cliche-ridden lion's den, because Imus was, would you say he was schizophrenic? Well, he was kind of a crazy guy, Imus, right? 

ROSENBERG Crazy, schizophrenic, angry. I never knew, was he mad every morning? Every morning. 

O'REILLY Every morning? 

ROSENBERG Every morning, and what he would do is, I was making about $1.50 at the time. He was doing very well because he was getting paid by both WFAM, which was a CBS radio property, and MSNBC. He was number one in the mornings. So he was raking in over $10 million a year. And he'd walk into the newsroom with WFM. There was a rule, Bill. You could never look at Imus. Not kidding you. 

O'REILLY Who? Who couldn't? 

ROSENBERG None of the employees at WFAN were allowed to look at him. 

O'REILLY Okay? What? 

ROSENBERG The newsroom employees. Not Mike and the mad dog and the talent. But the newsroom employees were not allowed to look at them. 

O'REILLY So the techs and people like that? 

ROSENBERG That's right. So he'd walk into the newsroom. And everybody would look down. 

O'REILLY Was there any explanation of why you couldn't look at Imus? 

ROSENBERG Well, he was, he wasn't handsome, man, so that was part of it. 

O'REILLY Right, it wasn't a drawback. 

ROSENBERG Like Medusa, you know, but he was just not intimidating. That it was a kind of a non-written rule. Don't look at him. But he would walk over to me, and he would lean over. This is like five o'clock in the morning, and he'd whisper in my ear, I need you to be funny today. And he'd walk away. And could you imagine, I'm 31 years old, I have all but three years of where you experience down in Florida under my belt, and here's I who at the time was at the very top of his game, he was really like stern, and he's saying to me, he's making 11 million a year, I'm not gonna be making 75,000, he's saying to me, I need you to be funny today. So when you look back at all my issues with Imus, and I was fired three times, suspended six times, I was in the papers every week, you'll understand why when you know the pressure he put on me as a young man new in this business. 

O'REILLY But some of it was your fault. 

ROSENBERG Of course. 

O'REILLY You know, you'd call people names, and they made it and do a much bigger deal than it should have been, but that road brought you into prominence, the Imus road. Then, people started to know who Sid Rosenberg was in the radio world. Okay, but in parallel to that, you got in trouble with drugs and gambling, two-fer at the same time? 

ROSENBERG And drinking. Uh, all three. 

O'REILLY Really? You had three. 

ROSENBERG Three. 

O'REILLY You had a hat trick. 

ROSENBERG I had a hat trick. 

O'REILLY Of depravity. 

ROSENBERG Yes. 

O'REILLY This is a good line. 

ROSENBERG That's a great line. 

O'REILLY Hat trick of depravity.  

ROSENBERG This is not Mark Messier against the Devils, this is a hat trick of depravity. 

O'REILLY Because you have a very nice wife, I mean, you do, and so you are doing this high-pressure show every morning, and you're gambling, and you're drinking, and you're drugging at the same time. 

ROSENBERG That's right. 

O'REILLY How'd you get through that? 

ROSENBERG I didn't. I. didn't.  I ended up getting fired. I ended up...

O'REILLY What'd they fire you for? Did they know you were a loon? 

ROSENBERG They knew, you know, back in 2004, for example, I went to Cleveland, a side gig. There was this early days of UFC, this cage match. It was at Cleveland State University on a snowy night during the winter. And it was a big night because they were having ex-NFL players fight against each other. Four-round fight. You know how that works. So Michael Westbrook, he was the wide receiver for the Redskins, took on Jared Bunch. He was running back for the Giants and bought a B and S for it that night. Long story short, I got about $5,000. I'm in Cleveland, and it was a Friday night, and when the fights ended, I wasn't going back to my hotel home alone, I was going down to the flats, the basement, that area, you know. And I got myself into a whole bunch of drinking trouble and never came home for two days. And when I got home... 

O'REILLY What does that mean now, trouble? They beat you up? 

ROSENBERG No, nobody beat me up. It wasn't any trouble with the cops. I mean, my own trouble. 

O'REILLY You were intoxicated. 

ROSENBERG I was intoxicated. I ended up taking a whole bunch of money out of the account, which I couldn't explain to my beautiful wife, Danielle. I'll be married 34 years this June. And when I got home, I had to explain to her what I had done. And I had already gone to rehab 10 years prior. And I said, Danielle, if I don't go back tomorrow, I'm gonna die. 

O'REILLY All right, so this is his second rehab. 

ROSENBERG Second rehab, 2005. 

O'REILLY And see how to know you're a little bit off and doing... 

ROSENBERG She knew, but she loved me, still does, obviously we're still together, thank God for her, and she just wanted to believe that I was okay, but the signs were there, I was struggling. 

O'REILLY So you knew you weren't okay? 

ROSENBERG No, I actually, at one point in my trip in Cleveland, which is well documented in my first book, You're Wrong, and You're Ugly, it was two days after I started the partying on Friday night, and I hadn't told Danielle yet why I wasn't coming home. I had a little bit of drugs left in my pocket, and I wanted to kill myself. 

O'REILLY Did that thought actually go through your mind? 

ROSENBERG More than a thought. I actually walked outside my hotel room. I was staying on the 14th floor. I walked to the very edge of the terrace, and I was ready to do it. I was convinced that my life was basically over. Here I am again, I'll be back in trouble, back in rehab, lost this amazing opportunity. More importantly, disappointed my wife. My son wasn't born yet, beautiful Gabriel, but Ava was. And I went into my pocket to take out what I thought was the end of my drugs, but I had two things in my pocket. One was the drugs, the other was a key chain to my house in Tanafly, New Jersey. And on the key chain... On the keychain was a picture of my daughter Ava, who at the time was about 18 months old. And when I reached for the drugs in my pocket, instead I took out the keychain. I looked at the picture, and I could have sworn, Bill, she said to me. Daddy, don't do it. So I put the keychain back in my pocket. I called Danielle, I said, I'm coming home. And I left the next morning for New York City. 

O'REILLY And then after that, you went to rehab. 

ROSENBERG I went to a rehab, and WFAN and Imus, all those people were very, very supportive. They let me... 

O'REILLY Well, Imus had his own. 

ROSENBERG He had his own. 

O'REILLY His own bounce. 

ROSENBERG At that time, he was probably sober about 15 years, but he was the epitome of a dry drunk. But nevertheless, he was sober, and he was very nice to me, and they kept my jobs, both the midday show host and the Imus sports job, for 30 days while I went away. And when I came back, I resumed both positions, but I wasn't well yet. And it didn't take me long after getting back to make an offensive comment or two, which eventually led to my termination in 2005. And that was the last time I worked a daily show at WFAN. And they did bring me back for nine years, till 2014, in an effort to get me back because they loved my talent and they liked me. 

O'REILLY Did you... This sounds like self-destruction, you know, that's what it sounds like. The conduct itself, that you felt you weren't worthy of the success, or I'm not a psychiatrist, but. 

ROSENBERG You sound like one. 

O'REILLY I know enough about life. It sounds like you had everything, which you did, but you didn't feel you deserved everything. 

ROSENBERG You nailed it. That's exactly what all my therapists said to me and Danielle, and there was a time I was going to a lot of meetings, 12-step meetings for alcohol, 12-step meetings for drugs, psychiatrists, psychologists, and they all said the same thing, that I had mastered the art of self-sabotage, that I wanted no part of any success. And as soon as I got to that point, because there was time at WFAN, I was doing the Giants pregame show in front of 10,000 people. Outside of Gate D every Sunday, and they love me. I was hosting the midday show with Joe Beningo. I was doing sports on Imus. I was in my 30s and started to become a legitimate sports star. And every time I got close, I did something to make sure I never got... 

O'REILLY You think that's what it was? 

ROSENBERG I think, yeah, I think some of it was this fear of, oh my God, am I worthy of this? Can I do this? I don't know for sure. You know, look, the truth... 

O'REILLY You were raised by decent people, I know Rosenberg, you were raised by decent people. 

ROSENBERG Very good people, and neither one of them had drug problems 

O'REILLY And you weren't abused, and you weren't thrown out in the street when you were 8. You're not a ghetto kid. 

ROSENBERG No. 

O'REILLY Had no money in the home to develop whatever you wanted to develop. So it had to be all within you. You say you relapsed, then after you came back. When you relapse, the guilt gets worse. Right? 

ROSENBERG It was terrible. It was, you know, I had gone to Atlantic City, and my wife was furious. They paid me maybe a thousand or two, it wasn't much. It was a fantasy football draft for a very popular magazine at the time called FHM magazine, and my agent Mark Lepselter at the time said, I'll take you, I watch you, we'll go, make a couple thousand dollars, and you'll come home. And everybody was against it. My boss, Mark Chernoff, said, you're not coming back. I said, will you stop it? I just got back from rehab, show some faith. Same thing with Danielle. They were vehemently against it. And I knew in the back of my mind that I was probably risking it, but that was part of the fun, right? That's part of, part of a thrill. So I went to Atlantic City, and I went to this party, and they paid me in cash, which was a big mistake. And I said goodnight to my agent, everybody else. And I headed towards the boardwalk, and there was a gentleman who rides those, they're kind of like buggies on the boardwalk, take it back to your hotel. And I had a couple thousand dollars cash in my pocket, and I said, hey, where's the party? And the next thing you know, it's Sunday morning. I'm supposed to go back and host week one of the Giants Carolina Panthers pregame show. Week one, I'm the host. My third consecutive year. My dad, who will be dead six years in July, man, do I miss him. He never missed a game. He'd be out there in his big Giants sweatsuit, all proud of me. And they were all out there waiting for me, and my agent came down to my hotel room, and I said, I'm not going. I had a pile of drugs in the room, I had booze in the room, and I was so ashamed and so afraid because I was really high. 

O'REILLY So you didn't show. 

ROSENBERG I stayed in Atlantic City. My agent, who comes under a lot of fire in my house, I think some of it's unfair, he did the best he could, he physically tried to remove me from the room. He actually had a bit of a fist fight. I did not come home, I stayed. 

O'REILLY Okay, so that's two you're dealing with now. So, finally you got yourself cleaned up from that, you went back to... 

ROSENBERG No, I did not get cleaned up from that. That was really just a couple of months after I went back to rehab for a second time. And I remember I took a cab home that night, it was $400. And Mark Chernoff said, listen, we gotta talk in the morning. And my wife woke me up very early, and she said, we're gonna drive to WFAN because I feel like you'll have a better chance of keeping your job if you speak to Mark Chernoff face to face. This is now 2005, and I've had two different major collapses and blowups. 

O'REILLY Right. 

ROSENBERG So, we started to make our way towards Queens. I'll never forget this. We're on the bridge, 59th Street Bridge, right there, and Chernoff called,  and Danielle picked up, and he loved Danielle, still does, we're still very close to this day. He's like a father to me, and he said listen. I've got some bad news, and she said don't even say it, We're gonna be there in 20 minutes. He said, don't come. And she said, but Mark, we're almost there, he said. He said, don't come, nothing's gonna change in the next 20 minutes, I love your husband. I think he is one of the most talented people. He goes, I've worked with Imus, I've worked with Stern, Mike and the Mad Dog, he's as good as any of them. But he's never gonna work here again. And it breaks my heart, and he started to cry. And Danielle started to try. And we turned the car around and went home. Now, mind you, mind you, that was 2005. It did not take 14 months for Mark Chernoff to call me back and put me back on Imus from Miami, which he did. 

O'REILLY You went to Florida in exile, right? 

ROSENBERG I went to Florida in exile. That trip...

O'REILLY Did you clean up down there a little bit? 

ROSENBERG I did. The trip to Florida, Bill, I have to tell you, we just bought this beautiful house in Tenafly, New Jersey. My daughter was home there the first night she was born. My wife loved that house, so did I. And I knew I was about to lose it. I couldn't pay a mortgage, didn't have a job. And I had a kind of a it was a nice size SUV car, and I put Danielle in the car, and I put my baby little girl in the car, and my dog Lucy. And I started a long trek from New Jersey down to Boca Raton, where Danielle's cousin Linda and George lived. They're still there. George passed away, but Linda is still there, and they offered to have us live with them because I had no money, no job. And I was driving and somewhere around Virginia, if I remember correctly, it was by Blacksburg, where Virginia Tech plays their football games, I started to just... Cry uncontrollably, and Danielle woke up, and she said, what's going on? And I said, I blew it. I don't know what I'm gonna do, I'm sorry. And it was a brutal trip, just thinking, well, Danielle slept most of the time, and so did my daughter. Thinking about what I'd done and the scarier part was not what I had done, but what was I gonna do? 

O'REILLY Right, you always had that balance where you might be more self-destructive. Now, you worked in Florida, right? 

ROSENBERG I did. 

O'REILLY Somebody hired you down there. 

ROSENBERG Eventually, I got a job at the number one sports station 790 The Ticket. Some very familiar names work there, guys like Dan LeBatard and Boo Shambi, and some big Florida names, and I worked there. I ended up working at three. 

O'REILLY Were you functional there? 

ROSENBERG Oh, more than functional. I was never not functional, even in New York. I never drank, or did... 

O'REILLY Were you still a drug addict, though? 

ROSENBERG Oh, oh sure. Listen, you know, it's funny, I saw Randy Grimes, he played for the Buccaneers on Fox News a couple of weeks ago. They brought him on to talk about Tiger Woods. And Fox News puts at the bottom of the screen, they go, former drug user, drug addict, drug addict, I'm sorry, former drug addict. And I called Randy, and I said, I gotta tell you, you're great on television today, but what do you think about Fox News calling you a former drug addict? And we both laughed. Bill O'Reilly, I will be a drug addict forever. Thank God, I am sober and clean for a long time. God has taken away the desire. I have no desire. 

O'REILLY Well, when did that happen? 

ROSENBERG It probably happened about seven years ago. You know, I still had my battles with sobriety down in South Florida. I'd be good for a longer time than I wouldn't. I was much better than I was in New York, but I was... Far from perfect. I was not perfect. 

O'REILLY Were you still going to rehab and stuff? 

ROSENBERG No, no, I did my two rehabs in 1995 and 2005. 

O'REILLY That was it for the rehab. 

ROSENBERG And that was it. 

O'REILLY Did you have a personal guy? 

ROSENBERG I had a sponsor, or I went to meetings, but probably not enough, you know? I started to feel pretty good about myself, and I was becoming a big radio star again, and you know, I was seemingly okay. But the desire was lifted many years ago. I don't think about it. I don't care. You know, there was a time. 

O'REILLY You don't know why it was lifted. 

ROSENBERG I don't know why. 

O'REILLY A lot of people say it's the higher power. 

ROSENBERG Listen, I believe that's true. I did get arrested once in South Florida. I had another terrible night, and I was leaving a Miami Heat basketball game and had gone to a club, and I decided I had to fight with Danielle that night. I was trying to get to the Hard Rock Hotel and Casino in Hollywood, Florida to sleep, to find a place to sleep. And I was about two miles away from the hotel and casino. I remember, I do remember pulling over to a residential community in front of somebody's house. Because I started to feel sick, and I knew I wasn't going to make it. And the next thing I knew, there was a cop in my face. So it turned out that I tried to exit the vehicle, I did open the door, I ended up throwing up all over myself, and I passed out. So a guy on a bicycle drove by and called the cops and said, hey, there's a dead guy. Literally, he said, there is a dead guy in his truck. Come get him. And the cops came, and that wasn't nearly as popular in South Florida as I am now, for example. I've, you know, I've gained some pretty good popularity, as you could appreciate, but I was pretty popular. And the cop knew who I was right away. And he said, you're lucky you're alive, but you're going to jail. So I called Danielle, my wife's a big-time attorney, and I said, Dee, I'm in trouble again, please come. And my kids were babies at the time, there was no babysitter at two o'clock in the morning. She threw the kids in the car, there were babies. And she arrived at the scene, and she said, listen, you know my husband, he's working really hard at trying to keep his life together. He had a bad night, no question about it, but if you arrest him, he's gonna be in the Sun Sentinel, he's going to be in The Miami Herald, and he's gonna be done. For the sake of my two little kids here, let me take them home. I'll take them all home, we'll get the car moved. And this cop, all he can think about was, are you kidding me? I'm gonna be in the papers tomorrow. I arrested Sid Rosenberg. I'm going to be on the news. So he didn't pay attention to Danielle. And they arrested me. And I remember, you talk about times when you start to figure out the gig is up. They placed their handcuffs on me. I'm sitting in the back seat of the police car. My daughter Ava, who is now 22, graduated Wales, Cardiff University in Wales, and is working with Arthur Idala. I mean, on some of the biggest cases in the city right now, she's an amazing kid. She's going to U of Penn for her LLM in a couple of months. She was seven. And I remember turning around in the back seat, handcuffed, vomit all over myself just... an embarrassment. And I remember seeing her crying. Like, why are they taking Daddy in that car? And I'm not going to tell you that I never drank or did drugs again after that because I'd be lying, but I will tell you, that was a pivotal moment in my life, and the amount of times that I did that after that, you can count on one hand. That was the beginning, I think, the beginning of... 

O'REILLY So Ava saved your life twice. 

ROSENBERG Ava saved my life twice, in my book, You're Wrong and You're Ugly, the first book I wrote, I actually referred to my daughter as my angel. 

O'REILLY So then you turn it around, and you get another shot at New York City. So you come on in, but you didn't have the same demons, or did you have the same demons? 

ROSENBERG No, I wasn't gonna do it again. I just, I still had them, I'm sure. Thank God. 

O'REILLY But you were able to conduct yourself on a day-to-day responsible level? 

ROSENBERG I was. 

O'REILLY Okay. 

ROSENBERG A lot of people, just so you know, Bill, a lot of people went out of their way to get me back. You know, Chad Lopez, one of them, everybody said to Chad, are you nuts? Including Imus. He didn't want me back. There was a... 

O'REILLY I mean, sure. 

ROSENBERG He wanted Mike Lupica. There was a big fight between who should replace Geraldo Rivera. Here were your two choices. Mike Lupica, doing the show from his house in Westchester and making a lot of money or getting Sid back from Florida, had a built-in fan base, teaming them up with Bernard, keeping the Imus thing going, pay them less, and have them do the midday show. And a lot of folks, the majority, including Don Imus, wanted Lupika. Chad Lopez said, nope, I'm bringing Sid back. He was not the only one. So here I am, I'm gonna, once again, have my wife move back to another state, take my kids out of school. And it occurred to me that I can't keep doing that and disappointing everybody. So it wasn't gonna happen again here in New York. 

O'REILLY Okay. But you're coming into a station that was last in the market. 

ROSENBERG Last. 

O'REILLY Brutal. 

ROSENBERG Dead. 

O'REILLY Okay. And then you take it to number one in the morning. 

ROSENBERG Yes. 

O'REILLY And that's a pretty stunning achievement. I've done it, so I know. 

ROSENBERG Yes. 

O'REILLY You have to work your butt off to do it. But you also have to have armor. Armor, because when you're on your way up, people try to drag you back down, you know how it is. 

ROSENBERG Who knows better than you about that? 

O'REILLY Nobody. 

ROSENBERG Nobody. Well, maybe Trump. They didn't try to shoot you three times, but close. 

O'REILLY No, but they would have if they could have. 

ROSENBERG Right. 

O'REILLY But you're on the ascent, okay? And I work with you, so I know it's because you're authentic. 

ROSENBERG Thank you. 

O'REILLY And New Yorkers, they want authenticity. They want people they can identify with, and you're that. But you're also a dope sometimes. 

ROSENBERG Yeah. 

O'REILLY Okay, which is okay in radio. 

ROSENBERG Of course. 

O'REILLY Television's a little harder to be a dope. 

ROSENBERG Yes. No, it's true. 

O'REILLY But anyway, you come, and then you make the show and carry the station with you, obviously, mornings are everything, into the position of prominence. Number one, did you know you were gonna do that? Did you have confidence? 

ROSENBERG I did. I did. I knew it, I, you know, the show I did in Florida, I had a guy, a couple of guys, you never heard of him. Their names were Steve Zimak, he's my producer, and Eric Lengel, they're gonna love this. You guys are famous. He was my board op. I approach the show every morning from a late-night television type of philosophy. So I said, here's what we're gonna do. We're gonna do all the stories we're supposed to do, whether it's politics or sports, but we're going to talk about music, and we're going to talk about our kids, and we gonna talk about lifestyle. Going to the restaurant last night, going to the ball game. So I knew that if I had the opportunity in New York to take that same exact show that I did in Florida and do it in New York, I'd have huge success. I didn't have that early on. Don't forget, we started doing mid-days, me and Bernard. Imus was still there, okay, for a good couple of years. And there was a time when Imus fired Warner Wolf again, and I was doing sports on Imus and the mid-day show with Bernard. When they finally forced Imus out, when he retired, and gave me and Bernhard the mornings, you know, we were working for Cumulus. John Catsimatidis, we had two other stations that were not doing great, WPLJ, and the nearest country station that actually was doing pretty well. So there were all kinds of issues, all kinds of issues. And to be honest, I love Bernard, and I miss Bernie every day. He was one of my best friends. I tell people all the time, I miss the on-air Bernie less than my friend. Not because he wasn't great or talented, he was. But we had two different notions of what the show was gonna be. He became this political animal, right? He was the cut-up guy on Imus, always getting into trouble, like you called me a dope? Bernard took that to the nth degree on Imus. Then he decided, listen, I'm 60-something years old, I'm about to have grandchildren, I gotta calm down. So he would get like 90,000 political cuts every morning and try to keep it really newsy. And I was still trying to do sports, and music, and fun. So when you listen to Bernie and Sid early on the morning show, it was almost as if you were listening to two different shows. 

O'REILLY Financial stress is hitting an all-time high. Millions of Americans are stretched thin with no extra money, no room to breathe. And this isn't just lower-income households. Middle-class families are also running out of options. If debt has been weighing on you, you are not alone. And waiting usually makes things worse. Interest grows. Minimum payments trap you. Nothing changes. You don't need another loan. Or to consider bankruptcy. You need a strategy. That's why I like Done With Debt. They build a smart, personalized plan around you and understand what it takes to work toward the biggest reductions possible. Whether you owe $10,000 or much more, their goal is simple. Lower what you owe so you keep more of your paycheck. Start with a free consultation at donewithdebt.com. Donewithdebt.com. 

O'REILLY All right, so you get into the position where you're dominating, and then you take a pivot into politics. You're the ultimate Trump guy, okay? So, did you know Trump before he got into politics? Did you know him? 

ROSENBERG I did. So I did sports, and I covered boxing. And for years, HBO had what they called Radio Row at all their big fights, Bill. I'm talking about Las Vegas, Dallas, Los Angeles, specifically Mike Tyson. So, I think I probably did my show live from the HBO Radio Row for Mike Tyson fights 20 times. Now, this is after his prison stay. So, you know, he's...the back nine, but he's winning. He's beating Francois Botha, he's beating all these basically tomato cans until he runs into people like Evander Holyfield and Lennox Lewis. But I would see Trump at these events, and Trump was a big Tyson guy, and I had him on the show once or twice. In fact, when he was on, not the last time he was on, the president, but the time before that, he was still campaigning, he wasn't president yet. We're going back a couple of years. And he said, you know, Sid, he goes, I'm proud of you. He said, You don't remember, which I do. He said, you don't remember, but I knew you when, when I was struggling. And let me say this about President Trump. He's never had a drink, you know this, maybe your audience does,  maybe they don't, he's never had a drink. He loved his brother, and his brother died from alcoholism. The fact that I've been able to maintain my sobriety and achieve what we've been talking about, sober and good, for all these years. If you don't think that's part of the reason why President Trump has this affection for me, not you, but you're somewhere between naive and stupid and closer to the latter. He absolutely loves that about me, that I put it away. I don't do that stuff anymore, he's never done that. So he said to me, he goes, I remember you when I was out at Super Bowl parties. I would see him in different locations, and I was whacked out. So I did know him, he did do my sports shows every now and then, but certainly not the friendship that we've got today.  

O'REILLY Okay. So, in New York City, a huge anti-Trump movement. When you became full-fledged Trump guy. 

ROSENBERG I mean, the worst. I'm the worst. 

O'REILLY Well, you love him. 

ROSENBERG I love them, yeah. 

O'REILLY I know. Did you take a lot of heat from the Upper West Siders? I mean, were you getting death threats and all that? 

ROSENBERG All that. So, God, you ask great questions. You know, in 2015 in Florida, I was still in Florida doing sports. And I had this lady, she worked at my sister's station. It was a political station. Her name is Joyce Kaufman. She's number one in news talk down in Florida. 

O'REILLY Yeah, I know Joyce. 

ROSENBERG Oh, you do? Great. So I would do her political show. She would do my sports show. And she loved Trump. And I'd say, what are you, nuts? Listen, I like the guy too, but the guy, he does a television show. How's he gonna run this country? We're a mess. Obama killed it. I hated Obama. I said, but this guy can't help us. So I came to New York in 2016, and the first year of my show with Brenard, the midday show, all we did was fight. That's all we do. He loved Trump. They have a nice little relationship. And I liked Trump, but thought he was, I thought he was one of the worst candidates I've ever seen. I actually told him that. I said I knew nothing about you. You're going to build a wall and wear a stupid hat. That's all I saw from you. What else were you going to do? 

O'REILLY So you weren't immediately on his team. 

ROSENBERG Bill, I voted for Hillary, and I told him that. He comes on with me and Bernard in 2017, and that's the first time we ever had him on. And I said, Mr. President, Bernard, ask him some question, I said, Mr. President, I say, I got to be honest, I've known you for years, oh yeah. I said I didn't vote for you. I said, I really didn't think you could become the president that you are today. So the good news is it took me about three months to come to the realization, you're the best ever. But the truth is, I didn't vote for you. I didn't buy it. Your whole campaign, I thought, was silly. So the interview goes on about another 10 minutes, and Bernard's about to wrap up the interview, and he goes back to it. He goes, how about it, Bernard? I changed him. I changed him. That's all he wanted to talk about was that, yes, he loved it. Listen, all the folks that loved him when he came down the escalator, he likes those guys. Even some of the folks that hate him. But you showed Trump somebody, who he was able to change to the guy I am today, which is the biggest Trump supporter in the world. He loves that. That's me. Didn't like him as a president. Took me a very short amount of time to figure out, boy, this guy's good. 

O'REILLY And then I know you're invested in Israel, and he's obviously an Israel supporter, President Trump is, and has helped Israel. So that was a part of it, right? 

ROSENBERG Well, when you say helped Israel, it's fair to say that no president in the history of our country has come even close. 

O'REILLY Harry Truman, he did a lot. 

ROSENBERG He did, but not Abraham Accords, moved the of course the embassy to Jerusalem, recognized the Golan Heights. I mean, I can go over 10 things that Trump did. Harry didn't do that. Harry's terrific, no question, but no one's come close to Trump. 

O'REILLY So then you become an activist on Trump's behalf, all right, and you go to Biden's State of the Union, and I don't know why they let you in, I certainly wouldn't have. Just the tan alone, you wouldn't have gotten by the door. And you yell out, okay, says who? 

ROSENBERG That's right. 

O'REILLY What did Biden say that rankled you there? 

ROSENBERG I'm going to tell you. By the way, I yelled that out, Alan Dershowitz, who announced last week he's now a Republican, after 87 years, he's a brilliant attorney, I love Alan, he's writing a new book, and he's doing a whole chapter in the book on me saying says who at that speech. He felt like that was a huge moment. Believe it or not, this is Alan Durshowitz. So that's surreal for me. So I'm sitting upstairs, right, because I'm not one of the House members. Anthony D'Esposito from your neck of the woods, he brought me to the State of the Union. I'm sitting upstairs, and at that point, we're really in the heat of the Israel war, real heat. And they're starting to get some unfair criticism from people in the United States and all across the world, and I'm getting angrier about the anti-Semitism in Israel every day. And I figure Biden's going to get to that in the speech, okay? He had hostages sitting up there with me, hostages, okay. Ten minutes in, nothing. 20 minutes in, I'm like murmuring, screaming under my breath, but it wasn't under my breath. So the CNN guy in front of me, the episode was going, hey, sir, could you calm down? We can hear you. I said, okay, I just, you know, I get frustrated. When's he gonna talk about Israel? 40 minutes in, nothing. Finally, about 50 minutes into this dreadful speech, and man, was dreadful. He was all jacked up on something, I don't know, so he wasn't falling asleep, but was awful. He finally gets to Israel, and he goes, listen. He goes, we, you know, we're friends with Israel, but according to the Palestinian Health Ministry, which you know, Bill O'Reilly, the Palestinian health ministry is run by... 

O'REILLY Hamas. 

ROSENBERG Bang. According to Hamas, he could have said, the Israelis have already killed 30,000 Palestinians. This is three years ago. My blood started to boil. I actually considered jumping over and just landing on top of him, and pummeling him, I swear to God. 

O'REILLY You would have been shot to death. 

ROSENBERG Of course. I don't know, these days, you know, they couldn't shoot our guy a couple of nights ago. But on a serious note, I stand up and I go, says who? And it took seconds. Three guys come rushing in, Capitol Police Secret Service. They grab me, and they say to me, sir, you have to leave. And I said, why? Look at those ladies down there with the white shirts, the Democrats with the white shirts. They're dancing, they're singing, they've got paddles, they're yelling, all this stuff. I said two words, I'm not going anywhere. So the Secret Service guy, Bill, puts his hand on my wrist. This is when you know I'm crazy. I go, you don't wanna do that. I'm talking to the cops. This guy could arrest me, and then it occurred to me, wait a second, I can't say that to him, you know? 

O'REILLY But it did occur to you. 

ROSENBERG It did occur. 

O'REILLY All right. 

ROSENBERG Yes, and he said, okay, well, here's the deal. If you don't get up and leave now, we're going to arrest you. We may arrest you anyway. But at the very least, give yourself a chance. So I exited the room. 

O'REILLY On your own will. 

ROSENBERG On my own will, Jim Comer is out there from Kentucky. Way to go, Emily Austin, one of your people from Nassau County, way to go. You're a hero. And I'm standing there for 30 minutes because the sergeant at arms was considering whether to arrest me or not. When they decided after 30 minutes, I can go home. I had to get Anthony D'Esposito, he was down in the chamber, to escort me out of the building like your daddy would do when you're eight years old at school, but needless to say, that hit the wires at NBC less than an hour later, and I became that guy, thrown out of the State of the Union, still one of my finest moments. 

O'REILLY Did you explain it to your kids that way? Because I'm sure they were curious about their father almost being exiled to Devil's Island, you know. 

ROSENBERG My kids always assume the worst. Yeah, they're like, Daddy, what'd you do? They love me, thank God, we're a very close family. They love me. They're proud of me. Tell me every day. I love you. I'm proud of you. But they always assume, Daddy, what did you do? When I explained it to them that the President of the United States was actually relying on Hamas instead of Israel. They said, good for you, Dad, way to go. You didn't go to jail. No big deal. 

O'REILLY Are you trapped in a timeshare? Fees rise every year while availability keeps shrinking and resorts make exiting nearly impossible. That's why I endorse only one timeshare exit company, Lone Star Transfer. They're family owned, transparent, committed to treating every client with respect while telling you the truth. Lone Star Transfer has helped more than 40,000 owners exit their timeshares legally and ethically through a simple, proven process. First, you receive a complimentary case review to confirm eligibility. Next, an exit strategy is customized to your specific situation. Finally, the Lone star Transfer team implements your plan, guarantees results. I have partnered with the owners for more than five years. Personally witness the outcomes delivered to our listeners. No surprise fees, no unused vacations, no stress, peace of mind. So please visit LoneStarTransfer.com or call 855-551-7066. 

O'REILLY All right. Then, uh, fast forward... 

ROSENBERG You go then, because there's been so many things already. You know, you started us off by saying you should have been dead. 

O'REILLY The goal of this, We'll Do It Live, is to destroy you. How am I doing? Am I doing all right? 

ROSENBERG You're doing exceptional work. 

O’REILLY So in March of this year, you called the mayor of New York, Mr. Mamdani, a cockroach. 

ROSENBERG That's right. 

O'REILLY Okay. 

ROSENBERG Well, that was the end of the statement. I also called them, because I don't care anymore, anti-American, anti-Semite, jihadist. 

O'REILLY All that's right, but once you get insects involved, then you've got, you know. 

ROSENBERG You know what's funny about that? You're right. And the insect part for me was, for me, when I wrote it, it was like the least inflammatory. Like, I just-- 

O'REILLY But you're from Brooklyn. 

ROSENBERG Right, we call people that. 

O'REILLY Right. 

ROSENBERG We call people insects, we. You know, look, there's an old slang word for homosexuals that we used in Brooklyn, had nothing to do with sexuality. 

O'REILLY Don't say it. 

ROSENBERG I'm not going to. But when you go with anti-American, radical, jihadist, all these things, I'm going, that's... 

O'REILLY Cockroach is way worse. 

ROSENBERG Yes, yes, I was shocked by that. 

O'REILLY But then there was an outcry in the city, generated by you know, Mamdani's people, of course. They got the publicity out of it. 

ROSENBERG Same night, Bill. Same night I went for, I tweeted this out, let's say it was four o'clock in the afternoon, seven o'clock that night I'm at my local Italian restaurant with my kids and my Twitter's... I look down Letitia James, hey Sid, I've never met her in my life, never talked to her, he's Sid, like we're best friends. This is Islamophobic, this is racist, I go, whoa, the attorney general. Before you know it, in the next hour, Governor Kathy Hochul. Former mayor Bill de Blasio, all of them, Julie Menon, the speaker of the city council, Jessica Tisch, who's my dear friend, we're very, very close, police commissioner, all of them. De Blascio, Ritchie Torres.  One by one, and they all wrote the same exact thing. 

O'REILLY Sure. 

ROSENBERG So, as you said to me, in a private phone call, which is now no longer private, you said clearly this was an orchestrated effort by City Hall. 

O'REILLY No doubt. 

ROSENBERG A thousand percent right. 

O'REILLY And you apologized. 

ROSENBERG I did, but there's a lot of erroneous reports. I read something even just yesterday to John Catsimatidis, my owner of my radio station, was interviewed. He gets interviewed all the time, you know. And they always bring me up. Hey, you got that morning guy, he's crazy. And he courses himself, and it said in the column that John Catsimatidis even at one point had to force me to apologize. Let me set the record straight right here on, We'll Do It Live. Nobody, and I mean nobody, not John Catsimatidis, not Chad Lopez, not my wife and daughter, who I spoke to the night before. Not the clergy people, who spoke the night before, nobody mandated to me that I must apologize. I've just been through this, as you've heard through this. Fired many, many times. I know how things all of a sudden take on a different life, even things that are silly, stupid. Right, so I just started on my own, there was nothing from my boss that said do it. I did it on my own, and I will tell you that that day I still beat the living daylights out of Mamdani. I just left some of those other words out. 

O'REILLY But you did the right thing by apologizing because you don't want to get down in the gutter with the Jimmy Kimmels, okay? I mean, I'm serious. 

ROSENBERG No, you're right. 

O'REILLY Because there's a line that you can cross that leads to insanity. 

ROSENBERG You're right, but... 

O'REILLY You don't want to be on the wrong side of the line. 

ROSENBERG Well, it's not like I apologized. 

O'REILLY You weren't groveling. 

ROSENBERG No, no, but it's not like I apologized, and the Democrats appreciated it. You know, I say this all the time, and you could appreciate this, but part of the reason why, Bill O'Reilly, you're a legend, okay? It's surreal that I'm doing this, and I mean that, I'm honored. I can't thank you enough. You're a legend. Part of the reason why is that a lot of people don't like you. President Trump is hated by millions. So it's now like I apologized, and now the Democrats and the folks that don't like me said, you know what, that's it. He's not such a bad guy. They hate me. They hate me, maybe even more. 

O'REILLY They'll never give you anything. 

ROSENBERG Right, so what do we apologize... What exactly are we apologizing for? For ourselves? I felt better. 

O'REILLY Now we did take a break for our Premium and Concierge Members. We'll come back. I have a very provocative question, not that I need it, with Rosenberg, who could go four hours. Okay, but I have a provocative question for him about New York City. So, for those of you who watch the We'll Do It Live, thank you very much. We hope you go and become Premium and Concierge members. Because then you get everything. We'll come to your house, we'll cut your lawn in the summer. We do all that. But I'll be back with Rosenberg in a moment.