With a 22 year career in Major League Baseball he became 1 of 25 players in history to join the 500 Home Run Club

He now has his own cigar line to commemorate the achievement
by Jon Shakill

Gary SheffieldThere are many exclusive clubs throughout the world, and many of them are limited based on financial status, political affiliation, having the right contacts, or being from the right family. Then there are the exclusive clubs that really mean something. The type of club that doesn’t discriminate, doesn’t care about your last name, and doesn’t care about where you came from. It’s the type of club that requires hard work, dedication, talent, and maybe a little luck – but above all, it’s based on personal achievement.

In the history of Major League Baseball dating back to 1869, there have only been 25 players to officially hit 500 Home Runs or more during their career. The 500 Home Run Club is one of the most exclusive clubs in all of professional sports, and a club based solely on performance. Gary Sheffield is a member, and one of the greatest Home Run hitters of all time.

With 509 Home Runs over a 22 year career in Major League Baseball, Sheffield was one of the most feared offensive players in the league from 1986 to 2009. Beyond being one of the biggest sluggers, Gary posted 2,689 career hits (65th all time), scored 1,636 runs (38th all time), and hit 1,676 RBI (26th all time). As a 9 time member of the All-Star team, Gary became the first player to represent 5 different teams in the All-Star game.

Gary Sheffield is one of the players who marked a different generation in baseball, where staying with 1 team throughout a career became less likely and all the more difficult to do. Like all professional sports teams, pro baseball teams are first and foremost in business to make money. Gary came to find this out the hard way during his career, impressing upon him the truth about loyalty as a Major Leaguer. But despite having played for 8 different teams during his career, and facing the constant reality of uncertainty, he was always able to stay consistent and put up top-tier statistics, making an impact wherever he went.

Starting with a bumpy road as an 18 year old kid on the Milwaukee Brewers in 1986, Gary was initially drafted as a pitcher. Seeing his strength and athleticism, managers would soon find that Gary was suited to play short stop. It didn’t take long for him to move to 3rd base, then finally settle down into his career position as an outfielder. Moving from the Brewers to the San Diego Padres, and having matured over his first several years, Sheffield won the National League Batting Title in 1992. Given his first dose of Major League loyalty, he was immediately traded to the Florida Marlins shortly after the season ended.

But it seems that everything happened for a reason during Gary Sheffield’s career, and undoubtedly so if you ask him. The Florida Marlins was a brand new expansion team when Sheffield was signed in 1993. Although some of his young idealism and loyalty had left him after being traded from the Padres, he decided he would do whatever he could to help build the new expansion team. Enduring four miserable losing seasons, the new team was essentially built around Sheffield. New players were signed, and things started to change. It was in 1997 that the team built on the shoulders of Sheffield would go on to win the World Series title.

Again given a lesson in Major League loyalty, all of the star players were immediately sold off and traded away after winning the World Series. Feeling left in the dust, Sheffield for the first time sought to be traded to a place where he could feel supported and given a chance to win. After taking a team to the World Series and seeing all the players leave, he wasn’t going to get stuck behind. The next stop was the Los Angeles Dodgers, where Sheffield played from 1998 to 2001. From then on, he moved to the Atlanta Braves for the 2002-2003 season, the New York Yankees from 2004 to 2006, then to the Detroit Tigers in 2007-2008, and finally to the New York Mets in 2009.

It doesn’t make much sense why a 9 time All-Star, recipient of the Batting Title and known Home Run slugger would be forced to move so much throughout his career, but it speaks to the business of baseball and professional sports, more than to the loyalty of an individual player.

Having since retired from a long and illustrious career as a Major League Baseball player, Gary Sheffield is today as content as ever. His latest endeavor is something that he’s dreamed about doing for as long as he can remember – starting his own cigar line. Just released at the end of 2012, the new cigar is known as the “HR 500” for short, or the “Gary Sheffield 500 Home Run Club Cigars.” Partnering up with Rocky Patel for the cigar venture, both men are excited for what’s in store.

Beyond the cigar line, Sheffield is also now running a sports agency called Gary Sheffield Management, where he helps players negotiate contracts, but focuses primarily on long-term legacy planning. Aside from putting his competitive drive and passion to work through business, Sheffield also tries to spend as much time as he can with his wife DeLeon and their 3 young children. I was able to catch up with Gary for the interview, between him picking up the kids from school and taking them to football practice, where he’s an assistant coach.

We turn now to the exclusive interview with Gary Sheffield, where we discuss his legendary baseball career, his cigar line, and what he’s up to now:

Gary SheffieldJon Shakill: Gary, you had a 22 year career in Major League Baseball. Did you ever think you would play that long? How did you have such longevity?
Gary Sheffield: Well I knew that I had the body type where I never got tired mentally or physically, and people always used to say “man you’re really hyper.” I don’t really sleep for that long, and I can go to sleep any time I want. You know, it’s like I’ll sleep for 5 hours and that seems to be enough for me. My whole thing was, if I happened to have a night out on the town or whatever, I had a policy that if I was going to hang out late at night, then I had to wake up at 8 in the morning and run 2 miles straight. Those were the types of challenges that I challenged myself with on an every single day basis. And I didn’t care where I was or what I was doing, that was just the rule. If I was hanging out and having a good time, then I had to be up at 8 o’clock and run it out. This started from when I was a young kid. I always used to do things to challenge myself, like if I didn’t meet a certain goal that I set for myself, I would have to do 100 push-ups. It was things like that where I really got my motivation and inner drive and inner strength. I took it upon myself to keep things basic, no matter what was going on around me or my surroundings, it was always that I still have to play the game today. If there’s something going on off the field, or on the field, or whatever, I knew that I had to worry about one pitch at a time, one at-bat at a time, one play at a time, and I always kept it like that. I would tell myself that I’m going to be out on the field for 2 and a half or 3 hours, and that’s where I would keep my focus.

Jon Shakill: Did you learn that from somebody? Or would you say that it was something innate in you?
Gary Sheffield: I learned some of it from my uncle Dwight and his work ethic [MLB All-Star pitcher Dwight Gooden]. I watched how for years and years, he was always known for practicing his swing by throwing cans up in the air and hitting them. From the time he was 8 years old all the way through graduating high school, he accumulated thousands of cans in our yard. Looking back at things like that I ask myself, where did this come from? It’s just that self-driven person. I think I got that from him and watching him get up every day and challenge himself to do something he hadn’t done before.

Jon Shakill: Over the years in your baseball career, you always posted good numbers. How did you stay so consistent over the years? Was it talent, hard work, or both?
Gary Sheffield: Well I think it was a gift from God, number one. I played a lot of sports as a child, and it all came very easy to me. Growing up playing football and baseball, if I wanted to dominate somebody I would do it. I played better when I was angry, as opposed to when I was happy. I used to always have teammates from when I was a kid all the way through the big leagues who would try to get me angry before the games, to get me to play even greater. My thing was, if I beat you I didn’t want to beat you by a little bit – I wanted to slaughter you [laughs]. So that was always the approach I took.

Jon Shakill: Given that you played on so many different teams during your career, what were some of the reasons for all the moves? Did you want to stay on one team, or were you ever forced to leave when you wanted to stay?

GAry SheffieldGary Sheffield: Sometimes people will associate one bad instance of leaving a team, with it happening every time you change teams. But when you look at my numbers, none of the situations were based on anything bad. It was just based on the teams not wanting to pay me. By the time I got traded from the Florida Marlins, I no longer had loyalty to any team – I was done with loyalty. With the first team I was on, the Milwaukee Brewers, it was a bad situation for me, although it taught me many valuable lessons that I was able to accumulate and that I needed. But by the time I got to the San Diego Padres, the first year I was there I won a Batting Title and was up for the Triple Crown. So how can you explain me getting traded within a month and a half of the season being over? It definitely wasn’t because of me in that situation, it was because of money reasons. That’s the one time I ever cried after getting traded, I was literally in tears. I was sitting out in the parking lot, where the players park, and I had a bunch of fans surrounding me, and I couldn’t believe it. I was pissed off. It hit home with me about loyalty.

Jon Shakill: What about the years you spent with the Florida Marlins and winning the World Series there?
Gary Sheffield: When I got to the Florida Marlins, and I posted great numbers there, I got to a situation where I could have become a free agent and walked away from what was then an expansion team. At that point I chose loyalty over anything else. I was loyal to them, I allowed them to sign other players, and I was one of the last players to sign a long-term contract. And it was because I wanted them to bring in players. So what happens? Well we had a miserable 4 years of losing, and I stuck it out, helped bring in new players, they got their contracts, and I finally got my big contract. Then we win it all in the World Series, and right after that, they traded everybody away. I had a blanket no trade clause, so I could have stayed after that, but why wouldn’t I want to go to a situation where I would have the opportunity to win? So then I looked at places like Los Angeles, New York, Atlanta, Detroit – these are places that I loved when I was there, but they’re places I could’ve avoided if I had stayed in Florida if I felt supported there. So that’s why any team that I went to, I was on my own program, and that’s why I did it that way. If they wanted me to buy into their system, I wasn’t going to do that, because their system was only going to allow me to be on the team for a little while, so why should I buy into anything?

Jon Shakill: It sounds like the business aspect of the league is set up so it doesn’t allow players to stay on one team for their whole career anymore?
Gary Sheffield: Yeah it’s changed. The way that I look at it is, if I come to your team and I’m leading the team in everything – Home Runs, RBI, batting average, I’m going to be one of the leaders in any of those categories. Every team I was on, I was 1, 2, or 3 – in those categories. So if I wasn’t being treated like a guy who was a mainstay, then I wasn’t going to do everything they asked me to do.

Jon Shakill: Tell us what the biggest contract you signed was, how much was it for?
Gary Sheffield: The biggest one I signed was for $72 million over 6 years, which was with the Florida Marlins. But I signed 5 big deals throughout my career. That was the single biggest one though.

Jon Shakill: What was your favorite team or city that you played for?
Gary Sheffield: I can say three places were really second to none at the time I played, and those were the New York Yankees, Florida Marlins, and the Atlanta Braves. It was great playing for the Florida Marlins at the time, because the city was on fire for sports teams. The Marlins were a new team, so everyone was into baseball, everyone loved the Miami Dolphins in football, and the Miami Heat basketball team was also new, so the time was just on fire. With the Atlanta Braves I really enjoyed playing for the coach, Bobby Cox. He set a great atmosphere there and the city was also great. So those were the three cities that I really enjoyed playing for. I didn’t play in San Diego long enough to really see all the beauties it had to offer.

Jon Shakill: Who are some of your favorite players that you played with throughout your career?
Gary Sheffield: Tom Gordon, Bo Jackson, Robin Yount, Glenn Braggs, Chipper Jones, Don Baylor, Dave Parker, people like that come to mind. I enjoyed being able to play with those guys. Chipper Jones was one of my favorites, he was one of those guys that was an even keel all the time. That’s the type of personality that I love to be around. I don’t like being around people that go up and down all the time – if they’re struggling then they’re mad at you and the world, but if they’re doing well then they want to be in your face and talking all the time. I don’t deal with them too much. But Chipper Jones was one of my favorites, and guys like that.

Jon Shakill: You joined the exclusive 500 Home Run Club, as 1 of the 25 guys in MLB history who’ve done that. Did you feel a tremendous amount of pressure to accomplish this towards the end of your career?
Gary Sheffield: Well I just continued to play my normal game at the end of my career. My thing was never based on how many Home Runs I would ever hit, even with my first Home Run – I never thought that I would hit a hundred because I just never looked at numbers. I never really paid attention to my numbers, I just played the game and played hard, and whatever the numbers were, that’s what they were. So when I was at 400, I thought I would get to 600. But then injuries started to creep in and it became overbearing. I had an injury with my wrist in New York, a shoulder injury with Detroit, and a couple things that prevented me from doing all the things I wanted to do. But as for the 500 Home Runs, I knew I was going to get there unless something freaky or fluke happened – otherwise my goal was higher than that.

Jon Shakill: So you didn’t feel the pressure to get to 500 towards the end? You just thought it was something you were going to do and didn’t have to worry about it?
Gary Sheffield: Right, well I never want to come across as being arrogant or anything like that – I just try to tell the truth of my situation and how it was for me as a player. I just felt like whatever I wanted to do on the baseball field, I could do it and no one could stop me from doing it. That was my attitude, and that’s part of the reason why I think I succeeded, I had so much belief in myself. If I’m ever put in a situation where it’s me against you, I’ll bet on me every time. It’s just the type of competitor I am.

Jon Shakill: Let’s talk briefly about that single Home Run that was the 500th. Do you have a great memory about that? Does the moment mean something special to you, or was it just another Home Run?
Gary Sheffield: No it wasn’t just another Home Run, it was the biggest one of my career besides the first one. Without the first one I couldn’t have hit my last one. With the 500th, I was a pinch hitter at the time, which I felt was a little more difficult because you’re facing a new pitcher and going up to bat for the first time in a game. I used to tell myself a thousand times that it was just my first at bat in a normal game, that I’m hitting third in the lineup, and I’m just coming up to the plate. But for some reason I could never get pinch hitting down pat. I struggled at that for some reason. But on that particular day, my parents, my wife, my kids and everybody were traveling around with me, and they couldn’t just keep following me for one at bat. I just said forget it, so that day I didn’t even think about it – I told myself I may or may not even get up to bat. So that particular day, I got up there, and I had a grooving at bat. I was fouling pitches off and asking myself how am I missing these pitches? If I was playing every day, I’d be sharper and hit all those balls. So I’m thinking, well at least I’m wearing the pitcher down – then the next thing I know, boom! When I hit it, this was the first time I can say that I was shocked that I even drove the ball like that, from a pinch hitting standpoint. When the ball went up I knew it was gone, because I knew the sound and that feel. It took me back to my rookie year, because the first person that I saw after I hit the 500th was Prince Fielder, and I remember when his dad Cecil Fielder would bring him around as a little baby. Then I saw a Milwaukee Brewers cap, and I realized that I was hitting the Home Run against the team that I first played with and hit my first Home Run with. So all those things were going through my mind. It was only fitting that I hit it against my old team. I originally wanted to hit the 500th Home Run with the Yankees, but they traded me, and it’s just funny how things come back around like that.

Jon Shakill: It sounds like your career came full circle at that point, hitting your 500th home run against the team that you played with when you hit your first home run.
Gary Sheffield: Yes, and that’s when I knew that God had something to do with it. I’m sure God doesn’t care who wins or loses, but things do come around full circle and have significance. I feel like it was all a journey that was already written the day I was born, that’s how I look at it. There was nothing that anyone could say or do that was going to change it from happening.

Jon Shakill: That’s a great story. Okay, so here is a question I feel like I have to ask; what are your thoughts on the controversy involving steroids in Major League Baseball over the last several years? Were you ever involved with it?
Gary Sheffield: I never saw anybody do it in front of me while I was playing. I think some of the misperception is that people categorize other supplements like protein shakes, vitamins you take, and so on, and group them together with steroids. Part of it was also the way the Commissioner and the Players Association went about things, they left a lot of players out to dry. It created a situation where players have to prove they’re innocent even before anyone proves they’re guilty. So if people come out and just say you’re guilty, now you have to prove you’re innocent. And how are you supposed to prove you’re innocent? I know a couple guys like Barry Bonds, who went back and fought it in court, and won on a technicality. So what am I going to go back and fight? Who am I going to sue? Then I’ll end up wasting millions of dollars to prove something that I already know I didn’t do, and if you win on a technicality, people are still going to say you did it. So for me it’s useless to worry about or to fight over. If that’s what you believe, then believe it.

Jon Shakill: It sounds like an atmosphere of being guilty until proven innocent?
Gary Sheffield: Absolutely, and that’s the thing. There are all kinds of things that help players get back out on the field, and help players get up for games, there’s different ways to do all of that with all the technology nowadays. And you can’t group all the supplements in with steroids, it’s wrong. But that’s the way a lot of people are viewing it. It doesn’t bother me one way or the other.

Jon Shakill: Do you think deserving players from your generation that were somehow implicated in the controversy should still go to the Hall of Fame?
Gary Sheffield: The Hall of Fame should be based on what a player has done during their career on the field, and what they’ve done for the game. We’re talking about people who have never played the game who are deciding who gets in. And to me, just because one guy doesn’t think I should go in, and another guy thinks I should go in, then how is that fair? You can ask guys that played against me during my career, and I can assure you we wouldn’t have this issue. To me, the system is what it is. It’s reporters picking who they like based on what they’ve seen, and some of the younger ones may have never seen you play before. Some of the older guys may not like you, or not care for you or whatever. I played for 22 years in the MLB and never won an MVP award, and I can count 5 years that I should have won it hands down. So if it’s based on a person’s vote for somebody, or based on whether they like you or not, then to me all awards and all accolades are watered down somewhat. I don’t have to politic to try to get into the Hall of Fame, if that’s what it takes to get in, then I guess I’ll never get in [laughs]. My whole thing is, if they vote for me then great, if they don’t vote for me then great.

Jon Shakill: Let’s turn to your life after baseball now. You wrote a book called Inside Power, what inspired you to write the book?
Gary Sheffield: A lot of people used to approach me about writing a book, and I always thought that nobody is going to care about my story, so why should I care to do a book? I had a few people who eventually convinced me that it’s significant to talk about these things, and so that’s what I did. My Grand Dad always wanted me to tell my story. So when I finally told my story, it turned out that it touched a lot of people and still does touch a lot of people. I’ve found as I’ve gone around a lot, that people who’ve read my book have gained inspiration from it. Looking back at it, there was a lot of emotion that went behind it and different feelings that I got, so at the end of the day, I’m glad that I did it.

Jon Shakill: What else are you doing now? I hear that you’re a sports agent now?

Gary Sheffield: Yes, my sports agency, Gary Sheffield Management, is based on legacy planning. I teach my clients the value of the dollar, and that they don’t have to go out there and do all this impulse spending. I help them to realize they don’t need to go around and prove to everybody how much money they have. The whole thing is, you can retire and walk away from the game and not have to try to find another job. That’s what the legacy planning is all about. I also work on the contracts for my clients, which is the easier part.

Jon Shakill: Who are some of your clients that you want to mention?

Gary Sheffield: The MLB pitcher Jason Grilli is one of my clients, and I also represent a number of minor league baseball players, who I care to leave anonymous for now. I’m getting into this business slowly, because I have so much going on. Of course I also have my cigar line, and other things going on, and I also value my time, especially with my family, so I have to do things in a smart manner – I can’t just be out there wasting my time.

Gary Sheffield cigarsJon Shakill: Let’s switch over to your new cigar line now; did you always want to start a cigar line and have you always been a cigar smoker?
Gary Sheffield: This is something that I’ve always wanted to do, but I didn’t know exactly how I was going to do it. Living in Tampa, Florida, I know a lot of people here who are big in the industry. But the way I wanted to get in, there were different ways to go about it. I could put my own money in with somebody and try to have them market it, or I could have somebody put some of their money in and market it, so it was a little tricky.

Rocky Patel was gracious enough to be that guy, who understood the vision of what I wanted to implement with the cigar. He was the guy who understood that if we do this, we have to push it hard, because I don’t want to fail and he doesn’t want to fail.

Jon Shakill: Give us some more information about the cigar. How long did it take to come up with it?
Gary Sheffield: It took us about a year to come up with this cigar, and we let it age, and after it was done aging, we felt like we had really hit a Home Run with it. Now as we’ve brought it out to the consumers, everybody who’s smoked the cigar says the same thing, that this is a great cigar and where can I get another one. The only critic I’ve heard so far said the cigar wasn’t strong enough – even though it’s medium to full bodied – which I’ll take that criticism above anything.

Jon Shakill: Is this a limited edition cigar, or are you going to continue to produce it? Do you have any plans to release more cigar lines, or do you plan to just focus on this one? Also, where can people get the cigar?
Gary Sheffield: No, we’re going to continue to produce this cigar, and we’re actually working on another one right now as we speak. I’m going to just keep putting them out there as long as we are successful in doing it, which I believe we will be. It is also available nationwide through cigar shops and lounges, or you can go to www.rockypatel.com and find it there.

Jon Shakill: When do you usually smoke a cigar? Where’s your favorite place to enjoy one? Do you enjoy any pairings?
Gary Sheffield: My favorite pairing with a cigar is Grand Marnier, and sometimes certain whiskies. Most of the time when I have a cigar, it’s after a long and strenuous day. I take the kids to school and pick them up, and take them to football, then we do all their homework and eat dinner, and the kids go to bed. That’s between me doing any work that I have to get done. So at a certain hour it’s time for me to unwind at the end of the day. That’s when I like to have a cigar and not think about anything. That’s when it works best for me, when I have personal time to watch a game or just relax.

Jon Shakill: Regarding your personal lifestyle, do you have any collections that you keep, like cars, watches, or memorabilia?
Gary Sheffield: Well I have my 500 Home Run trophy and plaque, and also some of the jerseys from other players that I’ve kept and so on, but honestly these days I sell most of that stuff. It got to a point where I had accumulated so much stuff over the years, and now that I’m retired I realized that I don’t really want a baseball house. So I think other people have more use for a lot of this stuff than I do. Jon Shakill: What do you usually like to do in your free time now that you’re retired from baseball?
Gary Sheffield: We have a place in Aspen, Colorado, a place in the Bahamas that we built seven years ago, and we have our place in Florida. So every year we go to our different places during different seasons. We’ll go out to Aspen and ski for about two weeks, then we’ll go straight from there to our place in the Bahamas for another two weeks. So we always get a good long vacation with the wife and kids. When it’s just my wife and me, we go down to Brazil every year and also to Hawaii. We always try to make time for each other and travel, and also go places that we’ve never been before.

Lincoln Salazar: Gary, who was your biggest role model as a man growing up and throughout the years and as a ball player?
Gary Sheffield: I had two main role models, my Uncle Dwight Gooden who was my mother’s little brother, and Hank Aaron. From both a pitcher’s and a hitter’s standpoint, those were two guys that I always looked up to. They both had the same type of personality, they were both kind of quiet and reserved but they were dominant players. I tried to follow that model for as long as I could, but my personality wasn’t like theirs was, so eventually I just stuck to being me.

Lincoln Salazar: What does it mean to you to be a man’s man and a gentleman? And what does it mean to you to be in this industry now?
Gary Sheffield: It’s very important to me because I’ve put in all the work throughout my career and evolved over the years, and finished out my career. I’ve been able to live out all of my dreams and aspirations. Now I get to enjoy all of the years that I’ve put in, and I get to enjoy different things that I want to enjoy, and I get to do it on my terms, which is the most important thing to me.

Jon Shakill: Alright Gary, thank you for your time and sharing your story with us and our readers.
Gary Sheffield: No problem guys thank you.