BY STEPHANIE COSTOLO & RANDI FREMUTH   |   PHOTOS BY BOB THOMPSON, THOMPSON BRAND IMAGES

At six years old, Orestes Destrade was on the run.

Born in Cuba in 1962 during the height of the Cuban Missile Crisis, life was challenging for the Destrade family. Parents, Leo and Elinsel, made the difficult decision to take their two sons, Albert (10yo) and Orestes (6yo), to America. They hoped a better life awaited them; one with opportunities for themselves and for their sons. In exchange, Leo and Elinsel had to leave their home, their friends and their families in Cuba and take a strenuous and dangerous journey in order to make it safely to America. Orestes remembers leaving Cuba, covertly traveling through Mexico with his family, and settling in New York for two years before making Miami, Florida their home. He was thrust into the American way of life and had to quickly acclimate to our language and customs. Everything was new and uncertain, except baseball. Sports were a love of his in Cuba and a familiar comfort here in America. As the years progressed through his youth, Orestes’s talent for sports of all types was evident, especially in basketball and baseball.

Today, Wesley Chapel resident Orestes, enters his 6th season as part of the Tampa Bay Rays/Fox Sports Florida broadcast team co-hosting the popular Rays Live shows, as well as appearing during select home games as an in-game sideline color analyst and Rays Spanish TV broadcasts. Orestes is also a brand endorser of several Tampa Bay Area businesses as their TV, Radio and Print Ad Campaigns celebrity talent. He played 1B/OF/DH for 15 pro seasons including in the Major Leagues with the New York Yankees, Pittsburgh Pirates and Florida Marlins. During that time period, he also played for the Seibu Lions of the Japanese Pro Baseball League, where he captured three consecutive Homerun and Japan Series Champion titles and became the first and only foreigner to ever lead both Japan Leagues in homeruns, 3 years in a row. Following his playing days, Orestes served as a Tampa Bay Rays front office Executive Director for 4 years before beginning his broadcasting career. Prior to joining the Fox Sports Florida family, he served for 5 years as a color analyst on ESPN’s Baseball Tonight and the Little League World Series. During that span, Orestes also hosted live national weekday radio sports talk shows on both XM Radio and ESPN Radio and made appearances on ESPN Deportes (TV and radio). Most recently, Orestes covered the 2014 and 2015 World Series Games for Univision Deportes as their lead MLB studio analyst.

As if all of that weren’t enough to keep him occupied through the years, he was recently involved with creating a documentary on Fox called CUBA: Baseball’s Final Frontier. Resident Magazine sat down with Orestes to get an inside peek into what it looks like to go from being an immigrant Cuban exile to an MLB player and successful sports broadcaster.

RM (Resident Magazine): Tell us about your childhood and family.

OD (Orestes Destrade): My mom Elinsel was your typical elementary school teacher when she came to the United States. My dad Leo was in construction, and he pretty much worked construction most of his life. He also drove a cab for 15 years at different times. My mom got her Master’s Degree here in the United States and always pushed education. She learned English and taught in an elementary school in Miami for another 35 years, so she taught for almost 45 years total. My older brother Albert is four years older than me, and he graduated from the University of Miami Law Schoo; he currently lives in Miami. Education is very big in our household. He and I are very close, and I think we really benefited from this mass exodus from Cuba and leaving everything, including our grandparents, behind. It was a very heart-wrenching experience. Baseball was huge in Cuba and still is. As a kid over there, and I took right to baseball and my family is very proud that I was able to become a major league baseball player; They’ve always been supportive. My mom really pushed education on us. My dad pushed practice (laughs). My brother and I were both very athletic, but we were both good in school too. I speak at a lot of schools now too, so now when I speak at schools my big statement is ‘Play Hard! Study Harder!!’

My parents are now 83 and 86 and doing great, and I’ve always felt the passion of my parents’ loss and leaving their country. These days, I’m even more taken aback by it because I started realizing that it was so close. We were 90 miles away; it’s very frustrating that this oppression and this regime created such a sad state, and I’m so very grateful that my parents gave us this opportunity to live this incredible life. We grew up in a very vibrant Miami in the ‘70s and ‘80s and learned we could be good athletes and do well in school. Both of my parents are massively important in my life.

I have 2 older kids from my first marriage; Devin, my son, just turned 25 in August and my daughter, Danielle, is the oldest; she turned 29 in December. They’re doing great; Devin lives in Nashville close to his Mom, and Danielle married her college sweetheart, Kyle. They had a baby three years ago, and she’s expecting in March. I’m an ‘opa!’ (laughs). Sadie is a sweetheart; she’s three and when she was born I said, ‘No grandpa! I’m Opa!’ My wife is Drisana, and I’ve got Armando, who’s 12 and Bella is 9. I’m impressed that all four of my kids were really good in school; they’re awesome. My younger two are both competitive swimmers with Florida Elite Swimming and doing really well in school at Corbett Prep. They’re outdoorsy kinds of kids and they seem to be pretty good about o be pretty good about entertaining themselves outside instead of in front of a screen. We’re just very strict about the allotment of time that is allowed with computer games and cartoons.

RM: Looking back on your life growing up, has your life gone the way you envisioned it would? What was your childhood dream?

OD: At eight years old, I was asked that question in school and I wrote that I wanted to be a professional baseball player. It was something that I always wanted to do because I knew I loved sports. By 12, though, I wanted Cuban in the NBA because I really took to basketball at that age. My brother is 6’2” and I’m 6’4”, and I was a really good high school basketball player. I ended up getting scholarship offers, but baseball really was the better choice for me. It ended up being where I wanted to be. If you fast-forward through my career, you get into the broadcasting aspect of it, and I’ve been doing this for 15 years. Some form of radio, TV, or both is exactly what I wanted to do. I really enjoy doing what I’m doing.

RM: When you think back on your life, what’s been a truly formative experience that has shifted the way you see the world?

OD: Early on, leaving Cuba was massive, but it didn’t really hit me at six years old. I was 18 years old as a senior in high school when my father went to the Mariel boatlift, which I think any American should Google and research. In that time frame, Jimmy Carter was the President and in a goodwill gesture, did a deal with (Fidel) Castro. Carter essentially said, ‘your people want to get out. We’ll take them,’ and Castro basically said, ‘okay, but it’s going to cost you $10,000 a person, and I can add whoever I want on that boat.’ So, what transpired was madness, happiness and sadness because thousands of people went to go get their family, including my father, who went to get my grandmother, aunt, uncle and their three kids. He went with a handful of other guys on a shrimp boat and was there for 34 days waiting in line on a boat at the port, just waiting for his turn to petition for his family.

Here’s the problem: Castro forced criminals and the mentally insane to also come on those boats, so for every one family member, he was throwing in 10 criminals, who came out of his insane asylums and out of his jails. The boat my dad went on with eight other people—that could only carry 50 people—was forced to leave with almost 300 people on it.

The boat capsized. 

My father and those with him on his boat survived, thanks to the efforts of the  U.S. Coast Guard, yet a lot of people were losing their lives. It was a horrendous situation and it backfired. In one sense, it was great because I got my grandmother back for a few years and my aunt, uncle, cousins, and other people’s family members came in, but that’s what created the madness of Miami. An area in Miami became a holding cell for all of these people that nobody wanted—thousands of crazy criminals that came on these boats. The boats would land and people would take their family members, but nobody wanted those people. Madness was unleashed because they were dropped in South Florida, and the law enforcement didn’t know what to do. So, they corralled them and put them in a stadium underneath an area called Krome Avenue. They fenced it all in, and kept these people there for a few years. Finally, they said, ‘we can’t do this,’ and they opened up the doors. This was the early ‘80s and my Miami turned into madness. It impacted me dramatically to the point where I didn’t want to live in Miami anymore.

RM: How did you end up in the Tampa area?

OD: The California Angels had drafted me out of high school, but instead of signing with them I chose to attend Florida College in Tampa, where I had great success in their baseball program and was named JUCO All-American. Before you knew it, the Yankees came running and let me tell you, for any Cuban kid, the New York Yankees personify freedom. I signed with them and even though it was a tough trek to get up to the big leagues because they had so many great players ahead of me, including a local product from Tampa by the name of Fred McGriff, I truly enjoyed my time with the Yankees. One of the things I wanted to do in life was wear a Yankee uniform at the major league level, and I did. I had a chance to play for Lou Piniella for a few months, got traded to Pittsburgh and then I was on my way to Japan.

RM: Tell us about your time in Japan.

OD: Japan was phenomenal. I was with the Pirates but there’d been some interest from Japan for a while, and I just decided one year to go. It was the greatest thing for me. It just fit me well. Part of the reason why it fit me well and other Americans go over there and struggle is because I had already done the migration thing and assimilated to a new country. I went over there with a big red carpet, nice money, and what I needed to do was just assimilate to the country and learn the culture, so I did. I learned the language, I learned the culture and I think that made me a much better ball player because I didn’t have the other struggles that a full-on American kid would go over there with. I fell in love with it, and I was fortunate enough again to be with the right team at the right time. We were like the Chicago Bulls of baseball over there. We won three consecutive championships and I won three home run titles, three RBI titles, and MVP. They ended up writing a book about me entitled Destrade The Seibu Myth. It was and still is a special place and I ended up going back there again in ‘95 and played there a couple more years before I retired.

RM: You had the opportunity to have lunch with Joe DiMaggio twice. What was your most memorable moment from those lunches?

OD: Being a Yankees fan, being a baseball fan and a baseball historian, I paid attention to the history of the game and what made it tick.

Joe DiMaggio made major league baseball tick.

I was fortunate enough that once I came back from Japan in 1993 to play for my hometown team, the Florida Marlins, I donated money to kick off a wing of the Joe DiMaggio Children’s Hospital. It’s an area for the parents to be while the kids are in surgery or in the hospital and I was very proud to help out with that. Joe, at the time, was living in the Hollywood area and doing a lot at the hospital and he took a liking to me. He watched me play, and I got a call that he wanted to have lunch with me one-on-one. It was the most incredible thing ever. Two times that summer (1993) I met with Joe and sat down and had lunch with him. Joe DiMaggio’s manager, Morris Engelberg, took me to the side and he said, ‘just don’t ask anything about Marilyn Monroe. You can ask anything, but don’t talk about Marilyn Monroe. He’s still very touchy about that subject.’ I said, ‘I don’t want to talk about Marilyn Monroe. I want to talk about Babe Ruth and the Yankees, and how it was.’ He was so gracious to me. The best stories I remember were about his 56-game hit streak in 1941 because that fascinated me. Anybody who’s a historian of baseball is always fascinated by that and how he was able to pull that off. He told me that when he started this streak, they were not playing very well. Then he went on this two-month stretch that nobody’s ever matched! When they came out of that streak, they were in first place and just kind of continued on. They won the Pennant that year and won the World Series. He was very proud that he made such a great impact on the team. He was just larger than life. I was too young to know him as a player per se, but in loving the game of baseball, I knew of him. That was special.

RM: With your documentary, CUBA: Baseball’s Final Frontier, what do you hope to accomplish? What do you hope people take from it?

OD: It’s a behind the veil look at a controversial country trying to deal with the United States and the political issues of an embargo lasting 60 years, and now players are trying to get out. It’s the struggle of the sport, but you can’t get away from the political aspect of it. I’m hoping that people can objectively look at it and realize how it is in Cuba. Unfortunately, the oppression is still going on.

RM: What do you do for fun?

OD: I love playing with the kids outside, goofing around… Anything with my kids. I’m big on Netflix and binge-watching shows. Right now I’m watching The Magicians.

RM: What is your favorite place to have ever traveled?

OD: Hawaii by a long shot. I think Maui is just heavenly. My wife was raised in Maui, so we have family ties there.

RM: What music were you last listening to?

OD: Last time I was listening to music, it was Nat King Cole’s, “Unforgettable”.

RM: What do you like about the Wesley Chapel/New Tampa area?

OD: There’s a great convergence of a lot of different areas, between Carrollwood, Wesley Chapel, New Tampa. Twenty years ago, there wasn’t that convergence. The reality is that it’s all kind of growing together and becoming one dynamic, powerful area. I’ve been around Tampa enough, starting at the USF area because of where my school was, and there was nothing out there but the school. I’ve lived just about everywhere you can in Tampa Bay, and I think that this area is very alive, growing and vibrant. I’m just very excited about the potential of it, and I think there’s still more to come.

RM: What was the last book you read or are reading?

OD: The Brothers by Leslie Downer. It’s a book about the owner of my team in Japan, Mr. Tsutsumi. It’s a tale of two brothers and their rise to billionaire prominence in Japan.

RM: What’s a regret, if any, that you have?

OD: It would probably be about Cuba; Part of me wishes that I’ve traveled there already, but part of me understands why I haven’t. There’s a pull in my heart about whether I should go back or if I shouldn’t because on one side, I have my parents who say, ‘stand firm. Don’t go back until it’s a free Cuba.’ There’s the other side of me that just wants to go see Cuba. It’s a very difficult thing in my life. I don’t know if it’s a regret, but it’s a quandary.

RM: What’s the best piece of advice you’ve ever been given?

OD: A gentleman by the name of Carlos Tosca, who was my first coach in pro-baseball and a Tampa native looked at me and said, ‘don’t fear failure.’ It stuck with me forever. I think in life that’s one of the struggles we have. We don’t attempt things or try things because of the fear of failure. Little did I know that I needed that advice because baseball is one sport where players experience a lot of failure. You strike out so much, you don’t get a hit, if you’re a pitcher, you can get lit up so much. Now, I always tell kids and parents, ‘don’t fear failure.’ The great thing about baseball is that you play a lot of games; you play more games than any other sport, so you’re always going to get another chance to get back up. This has been an important life lesson to me as well as in baseball.

RM: What was your proudest baseball moment?

OD: My proudest moment was getting called up to play for the Yankees in 1987. I also remember driving to the Yankee Stadium to play my first game there at the stadium. It was a massively huge moment getting off that road trip, flying to New York City, driving to the Yankee Stadium and listening to Phil Collins, ‘Hold On’ and the words ‘I’ve been waiting for this moment all my life’… It gives me chills thinking about it. I had a lot of family from Cuba that stayed in New York, so all of my of my New York cousins and my parents were going to be at the game, and it was amazing just stepping into Bob Sheppard saying, ‘now batting, #53.’

Secondly, it was Joe DiMaggio throwing out the first pitch of the April 5th, 1993 game. It was the first game ever in the state of Florida in a major league baseball game, and I was at first base. I got the first double in Marlins’ history and was the first Cuban-American representing Florida Marlins.

RM: In general, what pitch did you feast on?

OD: I was a switch hitter, so on the left side, I liked a low fastball, but on the right side, I liked the pitch to be up and over the plate. Those were my favorite. Another little tidbit that was pretty cool was that I was Randy Johnson’s first strike out in the Major Leagues.

RM: What pitch gave you a hard time each and every time?

OD: Anything thrown by Hall-of-Famer Greg Maddux. In Japan, they throw what they call ‘the forkball’, which is not a split-pitch. They throw a true forkball, and it’s a very difficult pitch to master… it’s like a ninja pitch. There was one particular guy by the name of Hideo Nomo; He was the master of it, and for a long time I had no chance against him. My coach taught me that he tipped his pitches, so when he came around back, you could see what pitch he was holding. The first 20 times I faced him I didn’t know this little trick, and he embarrassed me every time. After I learned his trick, the next 20 times, I crushed him for like five home runs.

RM: Who is your broadcast-style mentor?

OD: I like Hawk Harrelson. Buck Martinez taught me a lot also; I worked with him at XM Radio. I’m a bit of a mix of them both. Buck is a little more straight-up and very good, but Hawk is really more of what I’m like. Hawk’s out there and he’s kind of goofy and kind of crazy, but he’s really a baseball guy. Some people might not get it and some people might even say that about my style because I’m out of the box, but I think that’s what baseball is. Baseball has a lot of life and passion to it, and that’s what you want to hear on the other side. I’m all for good, straight calling, but especially for your color guy, he needs to be a little funky.

RM:  What’s the story behind you always holding the baseball?

OD: The baseball is an interesting story. If you know me, you know I don’t need a baseball to talk. I was on the field one day, on the air for Fox, and I grabbed the ball to demonstrate something. Being a Cuban, I’m naturally animated with my hands when I speak, and someone noticed that I was holding the ball and thought it was a nice touch. I started doing it every now and then, but it wasn’t every day. Tom Jones, the columnist for Tampa Bay Times, wrote an article basically asking ‘what’s up with Orestes and this ball?’ When I read that, with my bull-headed nature I decided that I would use that ball every day for the rest of the season. I held the ball every day, and by the next season everybody would say, ‘we love that baseball!’ Now after every show, I’ll have 8-10 baseballs that I’ve signed with ‘Play hard! Study harder!!’ If I see a kid, I’ll stop and talk to him or her about school and how important it is to play hard and study harder, and I give them a ball.

RM: So, you do put it down at some point?

OD: Oh, yeah. Honestly, I was a hitter, so I’d rather have a bat.

RM: Do you have any new projects in the works?

OD: I am excited to be joining the Rays in the position of Director of Baseball Community Outreach. It’s an all-encompassing kind of role; helping with their marketing and with the community—it’s kids, it’s charities, it’s businesses, it’s ambassadorship, if you will. Also enveloped in that is player relations with the players. I’m honored and excited about taking on this new role with the Rays.

RM: Thirty years from now, what do you want to be remembered for? What do you want your legacy to be?

OD: I still want to be doing a show for the Rays at 84 (laughs). My dad’s 86, he’s pretty spry. I want people to remember my positive influence as well as my time spent as an analyst. In every game I aim to educate people about baseball in a way that they can easily understand.

RM:  If you had could put a billboard anywhere and have it say anything, what would it say?

OD: The message that I have been giving to kids since 1993, ‘Play hard! Study harder!!’

There is not enough that can be said about the sacrifices parents make for their children. For Orestes Destrade, it was everything. Leo and Elinsel couldn’t be positive that everything would work out in America, but they had to try. They left their family, their friends and their home in hopes of something better, and Orestes knocked it out of the park. It doesn’t take a long conversation with him to recognize and feel the appreciation he has for his parents and the decisions they made. He also credits the incredible opportunities he’s been given to the U.S. and beams with community pride for the Tampa Bay area. Orestes has been living his childhood dream, not many of us can say that. He is an accomplished sports figure, broadcaster and advocate for children. He’s also down to earth, funny and playful. He continues to take his worldwide experiences and apply the riches of those moments to his community, here in Wesley Chapel and in Tampa Bay as a whole.