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Gary Sheffield Talks Cigars, Home Runs and Playoff Baseball

After playing 22 seasons in the major leagues he is now an analyst for Turner Sports
Oct 6, 2017 | By Kenneth Shouler
Gary Sheffield Talks Cigars, Home Runs and Playoff Baseball
Sheffield brings his southern accent and smiling demeanor to the Turner Sports studio.

A man’s man. The term defines Gary Sheffield. Across 22 major league seasons, he swung a bat with everything he had—an all-out hellacious hack. When he was through wiggling that bat at the pitcher in menacing fashion, he could launch a ball 500 feet. Sheffield played with eight teams and finished with 509 home runs.

Asked about his chances of making the Hall of Fame he said, “You are in the Hall or you’re not; there’s no in-between.” In other words, he doesn’t dwell on it. 

This man’s man constructed a man cave in his Tampa home, where he can light up one of his Rocky Patel HR 500 by Gary Sheffield cigars, a Nicaraguan smoke bearing his own name that is made by Rocky Patel. 

Now, with baseball’s month-long playoffs in full swing, Sheffield brings his southern accent and smiling demeanor to the Turner Sports studio, doing pre- and post-game analysis with Pedro Martinez, Jimmy Rollins, and host Casey Stern. We interviewed Sheffield this week to discuss his history, his love of cigars and his outlook for the MLB playoffs.

Cigar Aficionado: Playing Major League Baseball for 22 years is a long time. Do you miss the game?
Gary Sheffield: I did all that I wanted to do in 22 years, so it was one of those things where I had a lot going on when I retired. I didn’t have time to think about it too much, because I was off and running in other things that I was involved in. I didn’t reflect on it until about four years after retirement. And I looked back and said, ‘I don’t have any regrets.’ I did all that I had wanted to do. I had fun, it took care of me for the rest of my life. I don’t have to think about nothing like that. 

CA: What was waiting for you outside of baseball?
GS: I have been building this sports complex for seven years, getting that up and running for kids in the inner city. To give them an opportunity to play against kids that they wouldn’t normally be able to play against because of their financial situation. We are trying to bridge that gap and get these black kids back involved in the game and motivated to play the game. 

CA: Is that in Tampa?
GS: It’s right in Plant City, Florida, where the Cincinnati Reds’ complex is. We are in the process of getting investors behind this and build it out. 

CA: What do you enjoy about being an analyst for Turner Sports?
GS: I get to break down things. People have their own ideas and I have my own ideas about how I was successful. And you listen to other people that they say that made them successful. I am always intrigued by that. There’s not one way to do anything. There are a bunch of analytics in the game now. I like to look at those things and break them down and critique them a little bit. 

CA: What have you learned about television analysis?  
GS: How to give people their turn on the air, and take what they talk about and make it sound as one. It’s a group thing; there are a lot of personalities on there. You want to sound as one, but you want to put out your own ideas at the same time. 

CA: How do you find interacting with Jimmy and Pedro?  
GS: It’s a natural fit. I’m the more serious one, and they are the playful, joking ones. But they bring out the life in me, and loosen me up. I’m finding out things about myself every day by being around them. You know, you don’t have to be serious all the time. They have shown me how to do that without me compromising who I am. 

Sheffield on set with Pedro Martinez, Jimmy Rollins, and host Casey Stern.
Sheffield on set, second from right, with Pedro Martinez, Jimmy Rollins, and host Casey Stern.

CA: What are the different challenges in broadcasting? 
GS: You just have to sharpen your skills. You have to hone your skills and get better each time you step on the podium. You have to do that in a short period of time. Those are the things I am always fascinated by, getting better every day and seeing what I can improve. 

CA: What kinds of things are you trying to improve upon? 
GS: Just talking without slang. I’m a country boy. I talk country and I talk slang all the time. But I know how it is to be articulate and that’s what I need to be. But that’s not my common practice. 

CA: Cleveland is the odds on favorite to win—do you see it that way?
GS: I do—I do see it that way. I think it’s their time to win. They got so close last year. If there was a different circumstance, and it didn’t rain [between the ninth and tenth innings of game seven], then I think it would have happened. With the weather, it kind of interfered with what was going on. That kind of killed their momentum a bit. It kind of gave the Cubs an out to get back into the series. The same thing happened to us with the Yankees against the Red Sox [in 2004]. It just kind of killed the momentum, and it’s hard to get it back sometimes. 

CA: How long have you been smoking cigars?
GS: I’ve been smoking since I was about 18. I used to go down to Ybor City a lot; you see those guys hanging out, those old school guys, the Cubans and the Latinos over there. 

CA: What were you smoking at that time?
GS: I was smoking Montecristos, and we were getting some hand-rolled Cubans.   

CA: What inspired you to start?
GS: I always wanted to have my own cigar, but I wanted to stay away from making it cool while I was playing a sport. And I felt that way about it with kids being involved. But I said once I get out, that’s when I’ll celebrate my achievements. 

CA: Did you smoke at all when you were a player? 
GS: I smoked, but nobody would see me smoking. People knew I smoked cigars, but I didn’t do it in the open as I do now. 

I’ve been smoking since I was about 18. I used to go down to Ybor City a lot; you see those guys hanging out, those old school guys, the Cubans and the Latinos over there. 

CA: When did you find the time as a player?
GS: There were cities with hotels where you could sit on the balcony and have a nice smoke. I wasn’t smoking all the time, like a chain smoker. 

CA: Do you have guys you like to smoke with?
GS: Ray Lewis [who also has a cigar made by Rocky Patel], Jimmy Jackson, my best friend Calvin Sutton, Dee Anthony. We all like to laugh and when they come to town we all like to meet up at certain spots. There’s a bunch of guys who like to do the things that I do, and not be in clubs. 

CA: In the studio one night they replayed two of the home runs you hit off Pedro Martinez. And then you took out the cigar boxes with your brand and gave one to Pedro. 
GS: [Laughs] He said his mom smokes cigars, so I got it for his mom. 

CA: You and Rocky Patel agreed to make a Gary Sheffield 500 Cigar after your playing career. It’s a Nicaraguan cigar. How is that cigar doing?
GS: It’s doing wonderful. I didn’t get into this to get a ton of money. I just did it because I wanted my own cigar. I went out and toured 46 cities in one year—and it was taxing on me—to promote the cigar and pay my dues and give back to the industry. This is my passion, and people know that I’m involved with it, and now it sells on its own. 

CA: Since you are the nephew of Dwight Gooden, you were 16-years-old when he won the Cy Young Award in 1984. 
GS: Yeah, he got a Corvette for winning the Cy Young Award, and he gave me that car when I was in high school. I wound up driving that car to school, and a lot of people were envious of me. So I caught a lot of flak for that. 

CA: When you played with the Padres in 1992, you had a better batting average than your teammate Tony Gwynn. You hit .330 and won the batting title. 
GS: It’s a matter of what you choose to be as a hitter. I wasn’t just a batting average guy. I could hit for power, average, and drive in runs. I felt like I could hit singles on any given day, but I wanted to do more than that. 

CA: That season was the first that you hit more than 30 home runs and knocked in a hundred, at the age of 23. What were you thinking about your progress? 
GS: That was the first time I could play as I was capable of playing, without anyone telling me how to stand at the plate and not wiggle the bat, and things like that. Because I always had hitting coaches telling me to change that way I hit. And I wanted to hit that way. I thought I could be successful. When I got to San Diego, they told me to just be myself. If you think you can be a home run guy, then go ahead and be that. Because that’s what I did in the minor leagues. I hit home runs, I hit for average, and I drove in runs. Being a shortstop back then, that was something they didn’t see that much of—a shortstop putting up those kinds of numbers. It was like, they thought it was going to fail. 

Sheffield finds working with Martinez and Rollins to be a natural fit.
Sheffield finds working with Martinez and Rollins to be a natural fit. "I’m the more serious one," he says. "And they are the playful, joking ones. But they bring out the life in me, and loosen me up."

CA: You had your best offensive year in 1996, and you went to the World Series and won with the Florida Marlins in 1997. How do you recall those two years? 
GS: Numbers don’t lie, but I feel like when you win a World Series, that’s your best year. That’s all I cared about. The numbers are something that I was born to do. It’s nothing that I have to talk about to justify that I was a good player, or whatever. 

CA: In the Hall of Fame voting you went from 11 percent in 2015 and 2016 up to 13 percent in 2017, so is there a reason for optimism in 2018?
GS: I don’t think about it to be honest with you. All I can say is that either you are a Hall of Famer or you are not. So there ain’t no in-between. So that’s pretty much where I keep that. You either are or you are not. If it’s based on the decision of someone who didn’t cover you day to day, how would they know who is a Hall of Famer or not? If you didn’t cover me on a day-to-day basis, you’re just going on what everyone else said. 

CA: Do you think that you’re hurt by the allegation of steroids?
GS: I’m sure it is. Anyone who is going to assume something or think something is going to hurt you, but did it hurt Mike Piazza or [Jeff] Bagwell? I don’t think so. So, I guess not.

CA: That’s why I asked is there a reason for optimism, since Piazza, Ivan Rodriguez and Bagwell are all in, and they were also suspected. So the voting numbers might get better in the coming years. 
GS: At the end of the day, anyone who played in our era is going to get the same kind of flak, and that’s just part of it. You can’t go around that. Whatever. But I have always been upfront about anything and everything in my life. I’ve been an outspoken person my entire life, and I will stand up to anyone who wants to challenge me on it. 

CA: What do you see is different about the game now from the 22 years when you played, from 1988 through 2009?
GS: Well, I just think they rely on the big inning every inning instead of small ball. Nobody is bunting guys over and nobody is hitting and running just to create extra runs and put games away. You just go up there and if you strike out you strike out, and if you hit a home run, you hit a home run. That’s basically the way the game is played. And that’s just a new style of baseball. 

CA: I couldn’t agree with you more. You struck out just 1,171 times but you walked more—1,475 times. If you are going to strike out, you should walk as well. You shouldn’t have a three-to-one ratio of strikeouts to walks, as some players do now. Your comments seemed to agree with that.
GS: It’s not the player’s fault. It’s the establishment’s fault. If the establishment allows you to strike out, then you are going to strike out. If the establishment frowned upon you striking out—guess what?—you are going to try not to strike out. So your numbers may suffer, because you are not going to go up there and hit the ball out of the park. If they allowed my era to go up there and say, ‘Go ahead and strike out as much as you want, and hit as many home runs as you want,’ you would have seen guys with 1,200 home runs and 900 home runs. That’s what you were taught. 

CA: How does your wife [gospel singer Deleon Richards] tolerate your cigar smoking?
GS: She allows me to be me. I’m my own man. And if we’re in a place that bothers her, she don’t sit ‘round me. I built a man cave away from the house, so she doesn’t have to deal with it. 

CA: Is your man cave in Tampa?
GS: Yes, I built a man cave onto the house. It’s its own house—like I’m in my house.

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