Why you should care
Because when baseball’s most candid star talks, you should listen.
There’s a distinct sound that accompanies a great swing, and that echoing crack prompts lovers of baseball to instinctively look to the outfield bleachers. Since the late 1980s, few players have induced more mania on the diamond than Gary Sheffield. From thunderous home runs and gravity-defying defensive plays to occasional scuffles with opponents and umpires, Sheff was one of the most exciting players of Major League Baseball’s last 30 years. At least two decades worth of Little Leaguers, now adults, spent countless hours failing to imitate his beautiful, rhythmic and violent swing.
Sheffield had a Hall of Fame–worthy career, but as with many sluggers from his era, he will likely miss out on a Cooperstown induction due to the taint of steroid skepticism. He remains a fan favorite, though, not only because he was among the world’s most dangerous hitters but also because of his candor. Recently, OZY met with the Tampa Bay native to discuss his transition from player to agent to analyst, negotiating with the late George Steinbrenner and what steps the MLB must take to attract more Black athletes.
Until Major League Baseball catches up to that notion and embraces the hip-hop industry and the Black community, it’s not going to get more of us.
How can baseball attract more African-American athletes?
Sheffield: The only way that’s going to happen is if there’s a culture change. Young Black athletes are not attracted to a sport with zero Black owners, zero Black GMs. And there are no positive Black athletes in baseball on TV, building brands and standing up for change. You see LeBron James, Carmelo Anthony, these guys who own their own brands and stand up for social change — that’s what is attractive to young Black athletes today. Until Major League Baseball catches up to that notion and embraces the hip-hop industry and the Black community, it’s not going to get more of us.
How is your new youth baseball complex progressing in Tampa Bay?
Sheffield: It’s going to be huge. I wanted to get involved to help kids from where I came from. It’s going to be top of the line. But when you’re dealing with politicians, things move slowly. Development has to go through both the city and the state. Right now, we’re dealing with the state politicians and the distribution of money. It’s moving slowly.
What made you decide to retire in 2009?
Sheffield: A lot of players fizzle out in their late 30s, but I thought I was different. I took great care of my body, was always in top shape, never did drugs, didn’t really party. I felt like I could play as long as I wanted to. For me, it just got to a point where, mentally, I didn’t want to play anymore. I say play as long as you can if you still love the game, but I was done.
What sparked your interest in becoming an analyst?
Sheffield: Actually, it was at a celebrity golf tournament in Lake Tahoe. We were in the greenroom entertaining the guests, and I guess I was the one having a good time and making everybody laugh. After that, I was approached about doing TV. I had never thought of being on the media side; I didn’t think I would like it. But I auditioned with TBS, and I had only one question: “If I say something that’s borderline, something that might get me in trouble, do you have my back?” I didn’t want to waste my time with a network that didn’t have my back.
It seems like loyalty is important to you, careerwise. Is that true?
Sheffield: Oh yeah, it is. Right after I retired, I turned down ESPN because they asked me to come do TV, but they didn’t want me to bring my wife [around set]. After that, I knew I wouldn’t have their support.
You also run a sports agency. How did you transition from player to agent?
Sheffield: That was a transition I was going through while I was playing. I took it upon myself to do my own contracts. I was always involved with my contract negotiations. And when I went to the Yankees in 2003, with Mr. [George] Steinbrenner, God bless him, I personally negotiated my contract. After that, I felt like if I can negotiate with George, I can negotiate with anybody.
From there, it grew some legs. I realized that if I can do this, I don’t have to pay an agent 5 percent. The rest of my career, I negotiated $100 million in contracts myself.
Fans can watch Sheffield on TBS’ studio coverage of the American League postseason.