Jameis Winston, eater of dubs and giver of quotes, is perhaps the most singular personality in the NFL. The longtime quarterback has a reputation as one of the quirkiest players in the sport, evidenced by his bombastic pregame speeches, oddball warmup routines and unshakeable positivity in interviews.
But Winston’s joyful, seemingly carefree personality isn’t because he doesn’t know any better. On the latest episode of “No Free Lunch,” the 31-year-old sat down with Ndamukong Suh to share the steep learning curve for life in the NFL, specifically the hard lessons he learned about the money that follows success.
In the wide-ranging conversation, Winston shared his struggles to balance generosity and discipline, the cost of learning the difference between obligation and enablement, and what he believes are the most important lessons for young athletes in today’s NIL-fueled sports world. The discussion also highlighted what those close to Winston know well: His unbridled, often goofy personality isn’t because he’s naive; it’s because he chooses to be joyful. Here are the highlights from Tuesday’s episode:
If he weren’t a professional athlete, he would have been … a podiatrist?
Winston was a two-sport star, excelling in both football and baseball. He knew early he had the talent to go pro, but the career path he kept in the back of his mind, in case things didn’t work out, was podiatry, based on the success modeled by a woman in his community.
“You know, a lot of people always laugh at me when I get them that answer. And it’s based on the people that impacted me at an early age,” he explains, recalling the podiatrist in his childhood home of Bessemer, Ala. “She worked on my dad’s feet, mom’s feet, my uncle’s feet. Her husband, my mentor, he was a judge for the city. So I saw those two, that Huxtable moment where, you know, I saw that Black excellence. She was the person that I kind of, uh, navigated towards. She was taking care of two people that I loved very dearly, my dad and his mother, my grandmother. And I wanted to be a podiatrist, brother. Like, I really wanted to be a foot doctor.”
His first big purchase was a chair for his grandmother
Winston says he doesn’t remember how much his first check from the NFL was worth, but he does remember the number he saw in his bank account that let him know his life was changed forever.
“13.4 million dollars,” he recalls. “I saw eight figures in my bank account. When I saw that, I was like, ‘Yeah, I made it. I made it, but… yeah, I ain’t doing nothing with this.”
Winston decided, for a while, he felt more comfortable having that money than spending it, and when he finally did make a purchase, it was nothing more extravagant than a massage chair for his grandma.
“I bought a fancy chair. Like a La-Z-Boy chair for my dad’s mom, my grandma Winston. And I remember at the time the tag on that was like $4,600. It was one of those with the little compartments for your legs, where you could lean back and get the massage. Like your legs and back. She was a diabetic, so she was in heaven. To see that smile on her face and see how it actually helped her with her daily life. Bro. She was a nurse clerk for years at UAB Medical West, and at that time, she wasn’t retired yet, so for her to come home and sit in her chair and get that? You know, when you’re growing up, the only time you see a vibrating chair is in the mall,” he says. “And I got my grandma that massage chair. So that’s my claim to fame. And it was just $4,600.”
His biggest expenses were on relationships, and it taught him to establish boundaries
While the former No. 1 draft pick may not have spent lavishly on himself, it didn’t mean his money wasn’t being spent. Early on, he felt obligated to bring everyone in his life with him, but learned the hard way that he’s accountable for his money, no matter whose hands it’s in.
“You want to give them everything, but also it’s just like they were the people that you dreamed of it with. So like if you’re living the dream, then they got to live the dream, you know what I’m saying? Because it’s only right,” he said. “It got to a point where I enabled the people around me spending like $400,000 a month. A month, bro. Like on clothes, trying to do stuff on eBay — they called it trying to flip stuff. Because when you see eight figures (in your account), like, you’re like, oh man, this ain’t going nowhere. But when you read your monthly statement and you see that number (going down) and you’re not touching it, man.”
The answer for Winston was identifying who in his life was being enabled by his generosity, and who was being elevated by it. Where he and a close friend had a falling out over how his debit card was being used, Winston’s cousin used the money given to him to change his life.
“When I first came to Tampa Bay, I was giving my cousin, like, close to $300 just to take out the trash,” Winston says. “But for him, that was motivation. Because he was like, OK, I’m gonna take out the trash. I’m gonna use that. I’m gonna start a drive for Lyft, I’m gonna start finding my way. He used that $300 to pay for his own apartment. Like he was in the hustle mode. Yeah, some people don’t have that same hustle. Some people don’t have that same desire. Some people look at it as scholarships. Like, ‘Man, you got a free ride, now it’s time for me to get my free ride.’ To whom much is given, much is required, so it’s about having discernment on who can handle this and who can’t.”
When it comes to money, today’s athletes have to start learning early
The NIL era has enabled athletes to begin earning significant money long before they go pro, which not only changes their lives in the present but also offers protection against an uncertain future. That also means they face the challenges of financial management even earlier, often while they’re still teenagers. NIL would have been hugely profitable for Winston in his college days, but the challenges of being the NFL’s top draft pick were enough for him to urge young players to get educated before the money rolls in.
“When I got drafted, I was thrown into the ring of fire. A ring of fire. Financial advisors, agents, marketing personnel, and I had no experience with relationships with these people, you know? Me being a present, relationship-oriented person, I felt like it took me years to understand who they truly were to me,” he explains. “I knew money was going to come because of the work ethic. But I didn’t think about how I would steward it, bro. Like what I would do with it.”
The conversation dove deep into how to manage money and family, finding a “no” person in your financial life, and what athletes in the NIL era need to know a lot sooner than they think. Click here to listen to the full episode, or find it wherever you get your podcasts.
