Tell Me When It's Over is an interview series in which we ask former athletes about the moment they knew their playing days were over. Today: Jeff Sheppard, two-time national champion and one of the best dunkers in Kentucky history.

Sheppard won a title in 1996 under head coach Rick Pitino and then again in 1998 under Tubby Smith. That latter year, Sheppard also took home the tournament's Most Outstanding Player award, scoring 27 points in the Wildcats' 86-85 overtime victory over Stanford in the Final Four and 16 in their championship game defeat of Utah.


Sheppard—who had been named Mr. Georgia Basketball his senior year in high school—played 18 games with the Atlanta Hawks in 1999 and retired from the FIBA Italian League, and professional basketball, following the attacks of 9/11.

He runs the Big Blue All-Stars Basketball Camps, works as a motivational speaker, and owns the apparel company 15inc.

His favorite movie is Hoosiers, and though he and his family live in Kentucky, he has never ridden a horse.

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When I was in sixth grade I had to write a paper: "If I Could Trade Places with Anybody in the World, Who Would it Be?" And I wrote that I'd trade places with Larry Bird and play in the NBA for the Boston Celtics, but first I wanted to go to the University of Kentucky and play in the Final Four for the University of Kentucky. And that letter is now framed in my office.

God blessed me with the ability to play sports and run and jump, and I loved it. And because I loved it, I played ball all the time. When I got to middle school I stopped playing everything except basketball. I ran a little bit of track, but that was mainly just so I could jump. And so, yeah, I loved the game of basketball, still love the game of basketball.


I don't play much anymore, but I love watching the game. I love coaching my children. And it's what I'm remembered for. I still live in the state of Kentucky. It's a part of my life every single day. Even though I'm not directly coaching basketball or playing basketball, I talk about basketball almost every day of my life.

Everybody wants to know my thoughts on the current team. And, you know, we compare teams. That's what Kentucky fans do. It's what basketball fans do. We can't just watch the game and enjoy the game and then go on. We've got to [laughs] analyze it and we've got to talk about it and we've got to critique, and that's what makes it a lot of fun.

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It was in 2001, and I was in Rome, Italy, when the terrorist attacks happened on 9/11, and my daughter was just born. She was born in the United States, so my wife and my daughter were in the United States while I was over in Italy getting the season started. And they were getting ready to fly over and be with me in November, and, you know, that day changed the world. Especially the months and years right after 9/11—it just changed how we thought and how we traveled, and so we had to make some hard decisions, and I made one of those really hard decisions.

I didn't want to stop playing basketball from the athlete's perspective. I wasn't injured. I was with a good team. I was kind of established as a nice European basketball player, and I had another several years of a career, and possibly another cup of coffee in the NBA if the right situation presented itself. But at that point I was pretty much going to be an international, a European basketball player, and I could've had a few more years of that being my career. But I just felt that it wasn't the right thing to do to continue playing. It was better to be together as a family and then move on with the next season of my life.

And so that was the decision that we made as a family. I miss basketball, just playing. I miss the locker room and the team camaraderie and the travel on the bus, the wins and the losses more than anything. But that's how it was for me. And it's tough. I still dream about it. I still dream that I'm playing in different levels. I dream that I'm playing—I mean, literally, while I'm asleep, I dream that I'm still a basketball player some nights. But then the alarm goes off and I take a shower and put on a suit and go to work [laughs].

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I think that it's very possible that it's God's will to play the game of basketball as long as I did and then end when I did. Maybe one day I'll know the full story. My lower back was starting to give me some problems, and so maybe I was supposed to end when I did. Or maybe I was supposed to transition into the place where I am now. I do a lot of motivational speaking. I do a lot of programs for children. I do free basketball clinics and camps, and so maybe it was just time for me to get into this season of my life where I'm at a really neat position as a basketball player, living in the state and traveling around the state simply encouraging and influencing others. I believe that that's what I'm supposed to be doing now. You know, certainly selfishly I would've loved to have played a long NBA career and to be sitting on millions of dollars in the bank account, but I'm not and that's fine. I wouldn't trade my current situation for that, by any means. I've got a beautiful wife and family, and I get to spend a lot of time with them, teaching them basketball, and traveling around Kentucky and outside of Kentucky some as well. Being a former Kentucky ballplayer and professional basketball player is a really fun life.


You know, I tried out for several NBA teams and I got cut. I didn't make it. And so there's a certain area of my life, when I look at it athletically, that I'm disappointed that I didn't make the team, that I didn't get re-signed with the Hawks, that I didn't play more in the NBA and get hooked up with a team and win some games and eventually get with a championship club. That's the original dream as a kid. So there's a part that is disappointed, and then there's a part that says: "Wait a minute, Jeff. You did get to live that, no matter how short-lived it was. And no matter how you saw it playing out, you did get that opportunity." And so you put it in perspective. You have those moments when you're watching teammates of yours or competitors of yours and you're thinking, Man, I competed with him and played pretty good against him. But at the same time you glance over on the other side of your room and there are your children and your wife and you're healthy. So when you really sit back and put things in perspective, it doesn't control, truly, who you are. It's a piece of you, and there are regrets and things you wish you would've done a little different here and there, but we all have that. We just can't let that control us. It just needs to be the motivating factor that takes us to the next season of our life.

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We had opportunities, even years after 9/11, to return to basketball, and we thought about it. We thought about heading back over to Italy. But at that point I was already into my working career and we decided, Let's just keep going the way we're going. We're settled down. We're in a small town. Let's just raise a family the traditional way instead of bouncing from city to city all around the world. So, yeah, settling down at home and moving on was ultimately the decision that we made.


The thing that I had is, I had a lot of time in Italy by myself to really, really almost overthink everything. And that was tough because I didn't come home on September the 12th. The decision wasn't made right after September 11th happened. And September 11th affected me differently because I wasn't in the United States. I can't say that it affected me like I see events on television now that happen. It was more than that. I wasn't that callous to the situation—it changed the whole world. And it affected me as an American. But it still didn't affect me the way that it affected a New York City resident, certainly. But even someone who was in the United States and felt the panic that day—I didn't feel that. I was in Rome, Italy, and I didn't even have a computer. Everything I saw was on the news and it was on the Italian news, so I didn't know what they were saying. I just saw it. I talked to my wife. I knew it was bad, but I had no idea how bad. It was tough because I would talk to my parents, and my parents … I could just sense that it was, that this was something—I've never heard my parents talk like they were talking. But I still wasn't there. And so it was tough. It was a tough emotion that I felt.

But I did eventually get to that point: All right, what am I going to do now? And I didn't really get to that point until I was back in Kentucky and the dust had settled a little bit. And I talked to my coach, Tubby Smith—he was at the University of Kentucky still. And his first thing was, he said, "You're not done playing basketball. Keep playing." [Laughs.] And I said, "No, I think I'm done." And he said, "Well, if you're done, then come coach." [Laughs.] And I said, "Well, if I'm going to coach I might as well play." It's the same thing. It's the same schedule. It's the same routine.

At that point I had to determine: All right, what's next? What am I going to do? But that's OK. It was a tough point, but the neat thing is that I'm still able to stay connected to the game, through teaching the game. Even though I'm really not coaching as a profession, I still am involved with the game. I get to coach on a local level. And I may eventually get into some high school or college coaching one day, but right now I'm not. But I love to speak. As a matter of fact, tonight I'm speaking at a farmer's and businessman's banquet in a rural county in Kentucky. And it'll be a room full of Kentucky fans, and we'll laugh and tell stories and sign autographs and reminiscence and complain about this and that. And it's great.

Last year Rob Trucks interviewed current and former D-I basketball coaches Jay Wright, Mike Adras, Charles E. Ramsey, Murry Bartow, and Kevin Stallings as part of his oral history of 49-year-olds. His other work for Deadspin includes interviews with former NHL goalie Clint Malarchuk and the late Dave Duerson, and an oral history of Big Star co-founder Alex Chilton's time in Tuscaloosa. You may e-mail him at or follow him on Twitter at @tusktusktusk. Theme music and video courtesy Steve Wynn.