Jameis Winston has never shied away from honesty, and during a recent appearance on No Free Lunch with Ndamukong Suh, the New York Giants quarterback shared one of the most candid reflections of his career—this time, about money, family, and the hard lessons that follow success.
Winston revealed that early in his NFL career, his biggest expenses weren’t flashy cars or luxury homes, but the people around him. In an effort to bring everyone along for the ride, the former No. 1 overall pick said he unknowingly enabled spending that reached nearly $400,000 a month.
“It got to a point where I enabled the people around me spending like $400,000 a month,” Winston said. “A month, bro.”
He explained that seeing eight figures in his bank account early on created the illusion that the money was endless. That mindset changed quickly once he began tracking monthly statements and realizing how fast the number could drop—without him personally spending much at all.
Despite those eye-opening losses, Winston was clear that not every early purchase came with regret. One of the first things he bought after making it to the league wasn’t for himself, but for his grandmother—a high-end massage chair that cost around $4,600.
“I bought a fancy chair for my grandma,” Winston recalled, explaining how much joy it brought her after long days working as a nurse clerk while managing diabetes. For Winston, that purchase still stands as a meaningful reminder of why he wanted financial success in the first place—to improve the lives of the people who raised and supported him.
As his career progressed, the quarterback learned to distinguish between generosity and accountability. Winston shared how different people responded differently to his help—some using it as motivation, others viewing it as entitlement. One cousin used small amounts of money to build independence, while others treated access to his accounts like a “free ride.”
The takeaway, Winston says, was learning discernment. “It’s about having discernment on who can handle this and who can’t,” he explained.