Bobby Bonilla - Inside MLB's Best Contract Ever, Engineered by Dennis Gilbert to Pay $1.2M Every July 1st (Bobby Bonilla Day)

All right, welcome back to the Casey Adams Podcast. Today I am joined by Bobby Bonilla, the legend. Bobby, thank you so much for coming on the show today.

Oh, thank you for having me. I'm looking forward to the conversation.

Of course. So, you know, for the audience, we got connected through our mutual friend Dennis Gilbert, who I've gotten the pleasure of knowing recently. And, you know, I'm excited about recording not only today but this week because you know, as so many sports fans all over the world know that July 1st was the famous Bobby Bonilla Day. And not only am I excited to dive into your career, Bobby, but to talk about this day, to talk about the deal, and to really dive into your journey, which is, you know, what we always do here at the Casey Adams Show. So just to, I guess you could say, to kick off this conversation, every day when July 1st comes around, you know, the inaugural Bobby Bonilla Day, How do you feel throughout the week? Obviously, there's so much press and excitement. And I think so many people love reflecting on this moment in time that has remained to come up year over year from 2011. So how are you feeling this week? And what goes through your mind during a week like this?

I think it's fantastic. I'm feeling great. I'm just happy to have the opportunity to receive something on July 1st, which is a beautiful thing.

Absolutely. When I was at lunch with Dennis Gilbert last week, he was giving me his side of the perspective on your journey, his journey. And I want to take a step back. When yourself and Dennis, your agent at the time, were putting together this deal that has become to be known as this massive event in sports history, what were some of the thoughts and the conversations like? During the time when this was getting brought to you, how were you thinking about it and kind of where was your head during that moment in your career when, you know, it was not many deals like this or if any existed in the sports world, especially baseball. So like, talk to me about during that time.

Listen, at that time, at that particular time, I was always conscious of making sure I saved money so that I would have something when I was out of the game. Because one doesn't know how long this career is going to last. So the last thing you want to have happen is losing the money. You know, unfortunately, those kind of stories happen quite often. And I was so gung-ho on making sure that I just had money when this was all said and done. It was almost like it became my mantra, so to speak. Hey, just— whatever you do, make sure you have something when this ride is over, because one doesn't know when the ride is going to be over. I mean, I was lucky enough to play over about 17 years, and, uh, but you just don't know, right? All you could do is prepare yourself, make sure you're ready to play, and go out and do the very best you can, right? But, you know, one doesn't know what organizations are thinking or when the next great player is gonna come up. All you can do is keep yourself in shape, don't do nothing crazy with your money, and make sure you have something when it's all said and done. So Dennis, who has been a mentor for me for many years, also my agent, he's just somebody that's been very special to me, and he's always looked out for me and always made sure that I took care of the things that I wanted to take care of, and that one of those things was saving money. And he's pretty much the mastermind. Behind that. But there's a lot of— he set me up so well with obviously the deal I have with the Mets and the other various deals, but also with insurance. So I'm one of the lucky ones. What you want to do as a young athlete is read up on things that you're about to do, but also surround yourself with the right people. And I think that's the most important thing, is to make sure you do your due diligence and surround yourself with the right people.

Absolutely. No, I love that perspective. And, you know, I think just, you know, with today's conversation, I know over the years you've done so many interviews on your career in terms of the world of baseball. And I think kind of what you're hitting on thus far is really something that I personally would love to dive into even further, which is just, you know, when it comes to surrounding yourself with those right people, and, you know, I've had a handful of, young athletes on the show over the years, a lot of founders and entrepreneurs. And I think it same is true for not only sports and finding the right agents, but any business, right? It's like you need to be around people that have your best interests in mind that you can build and grow with. And when you were just coming into the league early in your career, when to go from undrafted to then becoming just an absolute legend in your respective field in baseball, How did you know that you were surrounding yourself with the right people? I think that many people may think they are, then they end up many years later it's not the case. So how do you kind of self-audit that, especially when you're early in your career, whether that's sports or business overall?

Growing up in New York City gave me a little bit of advantage. Yeah, it's easy to weed out people very quickly and That's what, you know, living in a big city taught me, you know, just having that opportunity to grow up in New York City was very advantageous for me because I could weed out people very quickly. And obviously you do your homework and you make sure that you are surrounding yourself with the right people. And don't be afraid. And I think the biggest thing is don't be afraid to, not be afraid to take somebody out of that circle if it isn't working out for you. I think too many times we hold on a little bit too long and sometimes it could be too late. But the ability to be able to weed somebody outta your circle is a nice thing to have. You know, hey, listen, this is not working out, you know. Yeah. You gotta go.

Absolutely. Absolutely.

You gotta go.

Yeah. Yeah. I love that. And even to just to kind of jump into the early innings of your career, 16 MLB seasons, 6-time All-Star, World Series. You've had quite the career in all states of the world. But I think so many of not only people like myself that love diving into stories in terms of sports and business, but the sports world overall where every July 1st, your name in this deal kind of continues to be talked about and just praised in terms of how unique it is. If you take a step back early in your career, what was your mentality around the future of not only sports, baseball, but truly setting yourself up? Where does that financial mindset come from? You know, the people around you. And I remember Dennis, you know, when I was with him last week over lunch, he would always say how you were, you were always asking questions, you were always curious. And, you know, I was asking him just in preparation for this potential conversation. And I'd love to ask you, like, where does that stem from, from your life, childhood, you know, early days in your life in terms of that curiosity to just ask questions and, and learn as much as possible?

Uh, you know, alluding to what Dennis said, I was always asking questions. One of the things I tell my kids is a closed mouth doesn't get fed. So if you're not asking questions, uh, I think you're hurting yourself. Uh, but going back to what led me to this was, you know what, my goal was just to play the game, play baseball. I really loved doing it, but I also came into a lot of money that I really didn't know what to do with. And all I kept thinking to myself is, oh my goodness, what would people say if I lost all this money? I don't know. I could just never get it outta my head, so to speak. So I was always, uh, how do I save this so I could spend like I'm an, uh, uh, tomorrow, like I'm an athlete today, so to speak. I don't know if I said that correctly. Yeah. But I was always afraid of that, you know, losing the money. So I wanted to make sure that I set up a situation where I had money down the line because we don't, like I alluded to earlier, we don't know when this ride is gonna end. So if all I'm thinking about is spending money and not really thinking about tomorrow, and don't get me wrong, I'm not trying to scare anybody. And if you want something, buy it. I mean, that's why you working your butt off, right? Is to enjoy the finer things in life. But you can only, I mean, how many cars do you need? How many watches do you need? How many bags do you need? When you really think about it, not to say not to have 'em if that's what you want, but I mean, how many of them do you need? I mean, my goodness. Yeah. If, but so I was always on that mindset to, I was really nervous about losing the money if I didn't surround myself with the right people. And, you know, our good friend RJ Reynolds, my good friend RJ Reynolds introduced me to Dennis, and we've been together ever since.

I wanted to dive into that conversation. I know Dennis would have, of course, appreciated it as well. Bring me back to the time when you first met Dennis and the kind of kickoff to that relationship overall.

Which is great. RJ said, "Listen, Bo." He knew I was looking for somebody to represent me. And he said, "Bo, look no further." You know? And RJ arranged for us to meet. It was in spring training. I think Dennis went to a Dodger game. I think we were in Vero Beach when we first met. But I'm not sure. Dennis could probably answer that better. But My recollection was I was in Vero Beach playing the Dodgers when I got introduced to Dennis Gilbert by RJ Reynolds, our good friend RJ Reynolds. And we've been together, we've been inseparable ever since. And it's been a great ride. It's been really a great ride. Yeah.

No, that's, that's so amazing. And, you know, I've seen so many great conversations and interviews out there, but I would love for my audience of a lot of young founders, I think, you know, for the reference as well, Bob, You know, I've interviewed lots of great entrepreneurs where, you know, we, we talk about this moment in their career, whether that's selling your company, whether that's getting the big deal. And I, I love asking them, you know, like, when that first check hit, or you kind of reach that moment, I think a lot of times that I've heard from the hundreds of interviews that I've done with some of the biggest founders in the world is like, maybe some feel empty, some feel complete, but it kind of vanishes quickly, and they're always thinking about the next thing. When you first got your first big deal in the MLB, and then of course this deferred year, which we'll get to, like, what were the emotions and the thought process as not only a player, but just as an individual who has been working so hard your entire life to maybe get to that point? Did the feeling last long? What was your mentality as an athlete when you're always striving for more? And kind of bring us back to that moment in your life.

It's really a good question, but my answer to what you asked me was I never was really thinking about money. I was always thinking about playing in the big league, and it happened to, uh, to work out. And it was such a privilege and honor to play. I mean, that's all I dreamt about. It wasn't really the money at all. It was nice, don't get me wrong, but the dream was to play in the big leagues. So I don't— all I remember is that, wow, this is nice, the money's nice, but it was never my main focus. And then once I started to make money, only thing that came to my mind was, oh my goodness, I don't want to lose this, because what would the stories be if I came into a lot of money and I lost it all? And I There were a lot of sleepless nights thinking about what to do with the money I was lucky enough to come into. And I say lucky enough because I put in the work, and it happened to come true that I was able to make a nice living playing the game. But my— it was always playing baseball was the first thing. And then all of a sudden, the money came. And through my hard work, I was able to elevate my salary. But it really was never— The goal, I know people will find that hard to believe, but the goal was really playing in the big leagues, being able to play in a World Series and playoff games. And the money was fantastic. But, man, once you made the money, all I could think about was, "On to— just don't lose this." Because the stories would be endless.

Yeah.

Yeah.

No, I mean, especially too, I think nowadays on, you know, with social media, there's a lot of young athletes that, you, you hear a lot of these stories in terms of athletes, you know, have these great careers, maybe they end up losing it all. And I think a lot of, you know, I'm friends with some young athletes as well, and I think that's— it's more common today, I'm sure, than what it was in your era of thinking about it this way, of like, wow, like, this has not been the case for so many players. Um, but I also want to kind of pinpoint and highlight, you know, you talk about this idea of of focus of just, you know, I'm focused on the game, I'm focused on the game. And of course, that's what made you great. And I think that's what makes so many great founders and athletes the most successful in their field is just that relentless focus and dedication. And on that note, I want to go back to when you were, you know, peak of your career on the field. What was your daily routine like when it comes to workouts? And what for you gave you that level of obsession when it comes to day-to-day staying focused on the next game and not allowing all the, maybe the stress or the expectations to weigh in on you. They kind of put me back in that place in the audience today.

Well, we can't look about working out now. But I guess my main focus before a game was just make sure I got a good meal in. Because we didn't really— because we played at night, it was important to make sure I got in a good meal before I got to the ballpark. And that's really all I thought about. And then make sure I put in all the work once I got to the ballpark to make sure that I was attentive, alert, to be able to do my job. And obviously having a good meal, making sure you're awake and aware of everything that's happening was I guess my key to success, so to speak. But yeah, but I think more so than anything was just, shit, I love, I love to play. Yeah, yeah, I just love to play. Yeah.

So one thing to kind of bring things to today as well, which I'm very curious about, is, is just, you know, how do you define success today, you know, in your life where you have this deal that's, you know, every year vanilla debt Pena days until 2035. I know you love golf. How do you define success today? And how do you quantify that in your life?

Success today? Oh, that's a very good question. You're talking about life after baseball?

Yeah, absolutely.

Yeah, once the career was over, I would just focus on being a great father, a great dad, getting out there, making sure I got to baseball games football games, basketball games, you know, golfing events, you know, because all the kids did various different things. You know, my oldest son is an avid baseball player. The next one plays basketball. He goes to college for basketball. And then the younger son plays collegiate golf. So my focus was them. I mean, that's really the only thing I thought about in terms of when I retired was to make sure that I was there for the kids. And my two girls, they've gone off to do wonderful things, completed college, which I'm proud of. One graduated Sarah Lawrence and one graduated NYU. And not to say that the other boys didn't graduate, Brandon graduated Grand Canyon University out in Arizona. John is getting ready to finish his collegiate career up in Humboldt. So—

That's amazing.

And yeah, and the golfer is up there at USF. So it's a lot of good things happening.

Yeah, I love that. When you were— in terms of— I like actually talking about golf a lot in different interviews, and I find that Throughout many conversations, it's a through line. When you were playing in the league, were you golfing back then, or was this something that came into your life after your career?

Not at all. But the introduction came to when we had off days when I was in the minor leagues and big leagues, and everybody would go, hey, let's go play a round of golf. I'm like, golf? I know nothing about it. So lo and behold, several years later, I might be in the offseason maybe doing 5 to 7 golf tournaments that I participated in. You know, scrambles are a great way to learn, uh, and I was able to learn to love golf that way through that. But it was the, the kids I played with in the minor leagues that introduced me, uh, to the game of golf. Believe it or not, I didn't play it at all as a kid growing up in New York City. Not at all. It didn't happen until minor league ball, and then obviously Uh, in the big leagues, a couple of days off, guys would like to go play, and— but we didn't, we didn't play a lot, you know, because I was— I played every day, so I didn't have time to work on the game, so to speak, like maybe the pitchers do. But, uh, man, it's a great game. Great game.

100%. Absolutely. I know I was telling you before we started recording here, you know, I've, I've been playing since I was with my grandfather, since I was young, and it's— I think it's one of those games that not only can you, you know, have these great conversations with people you play with, business partners, whatever it may be, but I think it's so relative to life. And I think what you talked about earlier around patience and focus, and I think as someone who grew up as an athlete, and you'd appreciate this, Bobby, but how I got into my own entrepreneurial career and business endeavors was sophomore year of high school, I was almost paralyzed playing football. I ended up in a neck brace for nearly 6 months and it was sort of this, you know, cold stop or cold start of couldn't play football anymore. My dream was to play lacrosse at UVA and had to kind of take this athletic ambition and poured it into, didn't really know what I was doing at the time, but starting a podcast and looking to meet great people, learn from them, create business opportunity. And that's led to a couple of different technology companies and just media business overall. And I think there's a through line that I've appreciated over the years of like sometimes in the deepest, darkest moments of your career, that's where obviously you can get built up the most and you can learn from and obviously propel from. I'd love to hear from you, like what were some of the hardest moments in your career that have, looking back, kind of defined the next phase or the next great event in your life that you can reflect on and look back on?

Oh, that's a very good question. But, you know, all I could say was I always thought it was a privilege to play in the big leagues, if I'm understanding your question correctly. I never took it for granted. Just the fact that I was actually playing in the big leagues, and it was something I dreamed about as a kid, still I marvel at. While we're talking about it, sometimes I have to pinch myself to say, man, did this really happen? 'Cause it was, it is such a blur. You know, me being in my 60s now and I'm reflecting on this wonderful career that I was able to participate in. I just never took it for granted. It was just special to be able to have the opportunity to play for the various clubs that gave me an opportunity to play with them and for them. I can't thank those organizations enough. It really is special to— and a privilege to play at the big league level that I never took it for granted. But going back to the money, I just— you never know when it's gonna end.

Yeah.

And that's why I was like, "Oh, man, I wanna make sure that I have money when this is all said and done." and I wasn't frivolous with it and did some stupid stuff with it. And obviously, you're going to do some crazy things when you're young, but as long as you learn from it relatively quickly, you know, good things happen.

Absolutely. You know, speaking of just being, you know, conservative and more so financially responsible as well, I, you know, I think in this modern era of baseball, of course, you see deals like with what, Um, excuse me, Shohei, his deal, and you know, they came out a handful of years ago around deferred payments. And I think whenever I saw that, and I think so much of sports media, sports journalism, a lot of people kind of reflect on your deal and the pioneering structure approach there. Um, you know, as someone that, as you said, like, you don't know when it is going to end, having this level of security and kind of forward-thinking ability. Um, when— and I know we talked this about this at the beginning, but just in the spirit of, uh, Bobby Bonilla Day, or two days ago and into July, um, one, like, how does it make you feel that you, you have this day that so many sports fans reflect on and look at and reference? You know, this is— it's, it's bigger than you, it's bigger than baseball. I think it's this cultural moment that, that so many sports fans, including myself, are just really love researching and learning about and kind of putting ourself in your position. So how do you think about July 1st, 2 days ago, and just the cultural impact of the day, the deal, your career, and the moment itself for baseball?

Oh, listen, I think it's very cool. It's actually bigger than my birthday, which is possibly another cool thing. More so if it creates awareness for people to, hey, I want you to listen. I'm not telling you not to spend money because that's why you work hard, is to enjoy it. But if you could think a little bit more about tomorrow, you're doing yourself a real service. You really are. I mean, I just want you to put a little thought into, hey, let me not spend it all now, but let me make sure that I'm thinking about tomorrow. And I'm being smart about it, you know? Surround yourself with the right people. I can't stress that enough. But, you know, just think, hey, let me think about tomorrow. Let me not spend it all today.

Yeah, absolutely. You know, one thing that, which led me to meeting Dennis that I have to bring up, 'cause I think you'll appreciate the story, but my good friend Chance King, who's the son of Larry King, I had Larry King on my podcast back in 2019. That's right after I met Chance. And at the time I was 19 years old doing the podcast. Larry King was 87. And of course we had this age gap and I learned so much through that conversation. And he has this quote that I reflect on a lot that I always love bringing up where Larry King said, you know, I've never learned anything while I was talking, therefore be a great listener. And that idea of being a great listener and to kind of what we talked about earlier around curiosity just stems into like broad-level mentorship. And I'd love to hear from you now, like throughout your career, especially even nowadays, like who are some mentors, you know, outside of Dennis? I know we've talked about Dennis for this conversation that you've been able to lean into, whether that's through, you know, fatherly advice, financial advice, business advice, um, and just really the power of mentorship overall. I'd love to hear your perspective on that.

I think it's important to have mentors. You know, when I look back, my dad was a huge, huge part of my life. He was always around, always came to games, always very supportive. You know, I was lucky. And then I always have to mention Dennis because a lot of reasons why we're talking about today is because of Dennis Gilbert. I mean, he always looked out for me and I've always looked up to him. And I gotta thank R.J. Reynolds for introducing him to me. I mean, when I look back, I can look at guys like Willie Stargell, Woody Hawkey, Steve Detmer. I mean, these guys, Pablo Cruz, who was always tossing balls to me in spring training. And I can go on and on about the great mentors that I've had, but Oof, you got me thinking. I've had a lot of wonderful people cross my path with nothing but positive things. You know? And I remember all of them. You know, Mako Olivares in Winter Ball. I mean, I can go on and on and on on how many wonderful people I've come across and been such a positive influence on my life. You know, I really don't want to leave anybody out. In any way. So, you know, you always, oh man, I forgot to mention this, so I forgot to mention that. But that's really not the case. Sometimes when it sprung up on you, like in these settings, you don't want to leave anybody out. But I've had a lot of wonderful, wonderful mentors, you know. Yeah, I mean, even BB, my good friend Box, you know, my very good friend BB, who should be in the Hall of Fame, by the way.

Absolutely.

We talk all the time and he's been a big influence on a lot of things. He's just another wonderful baseball player. Yeah. I mean, absolutely.

I love that. I love it. We could go on and on, I'm sure.

That's what I'm saying. I don't want to leave anybody out. Oh my goodness. Please.

Absolutely. No, I love it, Bobby. I have a couple more questions before we wrap up here, Bobby. I definitely, I appreciate your time so much today, but you know, something that I keep hearing from you, which I, I appreciate, and I know the audience appreciates, is just this idea of thinking ahead, right? Thinking about your future self and, you know, putting— setting yourself up, you know, with this, this iconic contract that has turned into Bobby Bonilla Day that we all love and appreciate, as we've talked about throughout this conversation. From, you know, 2011 till 2035, you're going to be getting these payments every July 4th. How do you, how do you think about 2035, you know, that final payment and life beyond that? And also —what that's going to mean to baseball and the deal overall. How do you think about that?

I never really thought about 2035, you know, because I pretty much live in the day. I don't try to think too far ahead. But obviously, that day will come, right? It's going to come. And, you know, I've surrounded myself with the right people to make sure I'm okay. When that stops. And I've set myself up for that. And with Dennis's guidance and Jennifer Prosperino, who is one of my financial advisors, with her guidance, things are going to be okay for Bobby Bowe. And that's all I can ask for. Yeah. So again, I've surrounded myself with wonderful people, and I'm going to be okay.

I love it.

Bo's going to be all right.

We love that. One thing that I always love asking every guest that come on the show, Bobby, that I think is just so relevant to this conversation, but if you could go back to your 18, 20-year-old self and give your younger piece of advice to your younger self, what would that advice be and why?

Okay, so the post— I mean, pre-big leagues when I was a kid or during the big leagues or after?

Pre-big leagues, what would your advice be to young Bobby in terms of life, business, really anything that speaks to you today?

Ooh, I would say now I would tell youngsters to Stay on top of your health. It's much more important than people think. You don't— that's an important part. Sometimes we get so busy with doing things that we're doing with the kids and your wife and family and everything, you forget about yourself. So I would probably tell myself, do a better job of taking care of yourself. Because that's extremely important because you want to be around to see your kids, kids' kids, grand— I mean, watch them play, or your grandkids and stuff like that. So take care of yourself so that you can enjoy what life's all about. Amazing.

I love it. Well, before we wrap up here, Bobby, I just— Yeah, yeah. —from myself and so many of the— many people all over the world, I wanted to say, Happy Bobby Bonita Day, but Bonita Week, I should say. Bonita. Happy Bobby Bo Day. Yeah. Yes. Yes. Bobby Bo Day. There you go. It really is so inspirational. And to see the cultural impact and the legacy that you've left on the sport and family and just so many people that are inspired by it. I'm so grateful for this conversation and really appreciate you taking the time to have this conversation with me today.

Thank you, Casey Adams. I appreciate that. It was fun talking with you.

Of course. Thank you so much for coming on the tip today. I really do appreciate it.

Appreciate you. Have a great day.