Few athletes were better prepared for life after football than Boomer Esiason. The former quarterback and 1988 NFL MVP for the Cincinnati Bengals has built a long and distinguished broadcasting career.
He currently co-hosts the Boomer and Gio show alongside Gregg Giannotti on WFAN Radio in New York City. He was a longtime studio analyst for CBS’s The NFL Today and game analyst for ABC’s Monday Night Football.
We recently caught up with Esiason to discuss how he successfully transitioned from the football field to broadcasting. We also asked him about Tom Brady’s TV career and his recent comments about Derek Jeter and Dave Sims.
Note: This interview has been edited and condensed for length and clarity.
Awful Announcing: Did you always think you would be a broadcaster?
Boomer Esiason: “I did. I (studied) radio, television, and film at the University of Maryland. I took two internships at WJZ-TV in Baltimore. I worked for Gayle Gardner. She was the sports reporter. I worked there for two years. At the same time, Oprah Winfrey was there. She was doing local news. But yeah, I cut my teeth at a TV station, and I loved it. I knew that eventually, hopefully, I would be on the other side of the camera. As opposed to being the interviewee, I would be the interviewer.”
So, you always had a post-playing career plan?
“I certainly had a plan. And what people don’t realize is that when I was playing, in 1990 and 1991, the World League of American Football came into existence. It was supported by the NFL. Warren Moon, Dan Marino, and I were hired as analysts in the off-season to do those broadcasts. The Monday night broadcast that I did for two years, I worked for Ken Wolfe and Craig Janoff, who were the producer and director of ABC Monday Night Football. I was, I guess, exposed, if you will, to all the trappings of doing a real game with real professionals, lots of cameras, lots of replays, and things of that nature. And I worked with Brad Nessler, who was awesome to work with.”
.@JerryRecco calls out Boomer for continuing to not invite him to events 😆 pic.twitter.com/Fz1VUrOgcG
— WFAN Sports Radio (@WFAN660) July 30, 2025
What was your big break?
“When I finally decided to retire, it was because ABC Monday Night Football, still under the guidance of Kenny Wolfe and Craig Janoff at the time, called me and asked if I would replace Frank Gifford, who was leaving. I said, ‘Yes.’ I jumped into the booth feet first. There was a lot of learning that I had to do at that level. It was a completely different set of circumstances than seven or eight years earlier on the USA Network.”
How can Tom Brady improve in his second year as a broadcaster?
“I think it’s just about being genuine. I sense a level of comfort with him and Kevin Burkhardt as the year went on. Tom has always been careful, never really controversial, especially when it came to football. Kind of followed the Bill Belichick way of talking about teams and things of that nature. And even meeting with Tom before games, he never really gave you much. He was always guarded. I think what you try to do is become as genuine as you can in the broadcast booth. I don’t necessarily know that anybody will be as genuine as the great John Madden was or Merlin Olsen was. Those were different times. There wasn’t social media impacting everything that’s going on. Not everybody’s going to love you as a broadcaster. I learned that pretty early on.”
Any other advice for Tom Brady?
“Hopefully, in year two, he’ll feel more comfortable and more confident and understand exactly what the viewers are looking for. I would also say most analysts these days are very careful. They’re not nearly as critical as some have been in the past. My former teammate Cris Collinsworth probably falls under that category because when he started in TV, he was covering a lot of my games. I had a couple of bad games, and I remember him being pretty critical of the way I was playing. Richard Sandomir was a sports TV columnist. Richard gave, I think, Cris five stars because he was able to criticize me, his former teammate. Chris was much more critical back when he first started.”
How much do you miss not being on NFL Today?
“I don’t miss it at all. I loved my 22 years there. They treated me professionally. Sean McManus treated me amazingly. I had a great boss. I’m still a part of their family through CBS Sports Network, which shows you that they still wanted the content that I was able to deliver. But I finally got my weekends and the fall back for the first time in 40 years. I just forgot how great the fall is in the Northeast.”
What is the secret behind your long radio career?
“First of all, you’ve got to have good partners. You’ve got to work for serious companies. For me, it was working for Westwood One, CBS, WFAN, which was CBS Radio and is now Audacy. And having my bosses completely trust me on the air, I feel like I’ve always been in the right spot around the right people. It didn’t always start that way, but certainly over the last 22 years, 23 years, it worked out great for me. It was a bit of a learning curve when I first started back in 1998, 1999. But once 2000 rolled around, the last 25 years have been pretty smooth sailing for me.”
Boomer Esiason doesn’t buy Derek Jeter’s birthday excuse for missing Yankees Old-Timers’ Day pic.twitter.com/bTUoXGxPM1
— Awful Announcing (@awfulannouncing) July 29, 2025
Have you heard anything new regarding what you said about Derek Jeter and Old-Timers’ Day?
“Only what Tiki Barber said. I guess he saw him up at the Hall of Fame induction for CC Sabathia, and that he was angry with me. Well, for 18 years on this radio station, I’ve been talking about how great he is. What a great leader he is. What a great example he is for younger players. He never called me to say thank you, so if I got under his skin one time—and I prefaced it by saying if there’s a family event he has to be at that can’t be cancelled, then I can totally understand. So, that’s all I heard. I heard it out of Tiki’s mouth. I don’t worry about it too much. I don’t lose too much sleep over stuff like that.”
Do you have any more details you can share?
“I think that there’s something there between Derek and the Yankees. I don’t know what it is. I think he’s visited them maybe four or five times since his retirement. But I also know that this particular thing that I believe he has conflicts with the Old-Timers’ game on Aug. 9, and is something he has to be at. I was contacted by somebody, I believe in his inner circle, who told me what it was, and I said that met my criteria for him not being there. So, I’m solid with it. I do not back off on anything I say. I get paid to give an opinion, and that was my opinion.”
Have you mended fences with Dave Sims for what you said about him taking time off during the Yankees season?
“What are you doing? You just took the Yankee job! It’s supposed to be the job of your life.” – Boomer Esiason has an issue with Yankees radio voice Dave Sims already taking a series off. pic.twitter.com/TBs9aOgtZf
— Awful Announcing (@awfulannouncing) May 12, 2025
“Dave called me, and when I answered the phone, I said, ‘How’s vacation going? I didn’t realize you were taking off 40 games into the season. I’m sorry.’ He told me again that there was a personal reason. (It) was very important to him, and he worked it out with management. I said, ‘Well, nobody told me that. I was just wondering why you were off 40 games into the season when you replaced a guy who never took a day off.’ I think we both had a laugh at it, and that’s where I left it. I don’t know where he is with that.”

About Michael Grant
Born in Jamaica. Grew up in New York City. Lives in Louisville, Ky. Sports writer. Not related to Ulysses S. Grant.
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