For professional athletes, true financial success goes beyond signing big contracts or landing endorsements. It’s about making smart decisions that transform short-term earnings into lasting wealth.
In this series, I interview athletes and entertainers to explore how they’ve navigated their careers’ financial highs and lows—learning from big paydays, unexpected challenges and strategies that set them up for lasting success.
This time, I sat down with Malik Jackson, a Super Bowl champion, 10-year NFL veteran and founder of The Care League, a wellness and mentorship platform for players. Over a decade in the league with the Denver Broncos, Jacksonville Jaguars, Philadelphia Eagles and Cleveland Browns, Jackson experienced both the pitfalls and triumphs of financial life as a professional athlete. Now, he’s helping the next generation of athletes prepare for life after football—financially, mentally and physically.
Evan Vladem: Let’s kick it off with a hard-hitting financial question. Have you ever thought about selling your Super Bowl ring?
Malik Jackson: People care about you having a Super Bowl ring when you win it, but you can’t buy groceries with it [laughter]. No, I’ve never thought about it. It’s more sentimental than monetary.
EV: You didn’t just win a Super Bowl, you scored a touchdown in it. What did that moment feel like?
MJ: Overwhelming. Especially as a defensive tackle. Von Miller comes off the edge, makes a great play and suddenly the ball’s there. I’m like, “Whoa! Get it!” I hop on it, and we’re in the endzone. I roll over, get up, and say, “No way, I’m in the endzone!” I start running, realize I don’t have a touchdown dance, and just said, “F-it, stands! Whew!” [laughter] I wish I had that ball, but I remember it mentally.
EV: You started at USC and then at Tennessee before NIL existed. What was the financial reality of being a D-I athlete back then?
MJ: I wish I had NIL. These young adults have such a great head start. Back then, it was Sallie Mae and getting cash under the table. I’m glad to see them earning, even if it’s complicated. But with more money comes more responsibility. I hope they’re getting educated and guided the right way.
EV: Some 17-year-olds are becoming millionaires before playing a snap. That’s a lot to handle.
MJ: Exactly. What can a parent tell a kid making more money at 17 than they’ve made in a lifetime?
EV: As a fifth-round pick, your first deal wasn’t massive. How did you make it work?
MJ: My first contract was four years, $2.1 million. At the time, I thought I was rich! But after taxes, agent fees and lifestyle, reality set in. My financial advisor didn’t put me in the best position. I was spending straight from my account with no credit and no plan.
When you’re teammates with Von Miller, Demarcus Ware and Peyton Manning, guys making multi-million-dollar salaries, you realize you can’t keep up with their lifestyle. I eventually moved on. My new advisors taught me budgeting, the difference between needs and wants, and how to build for retirement. That helped me set my daughter up for generational wealth.
Now I’m more conservative—no more calls about Ferraris or Paddocks. When you’re young, it’s tempting. Seeing your teammates on private jets, buying houses and jewelry … while I’m flying Frontier [laughter].
I made some mistakes, but because my second advisor helped me plan for the future and gave me some runway, I’m still good for the long haul.
EV: Were you investing early on?
MJ: Not really. If I didn’t get that second deal, I’d probably be cleaning the building you’re working in. That’s the reality for a lot of guys. They try to live the big lifestyle before they’ve earned it, not realizing the second contract is what truly sets you up.
EV: When did the second advisor come in?
MJ: Around my fourth year. My best friend told me my advisor was tied to a scheme. I didn’t even know what that meant. I moved on and brought in a new team. It really saved me. My first advisor ended up going to prison. I had nothing left from that first deal, and I didn’t even know what actions to take.
EV: That Super Bowl season helped you land the big one, right?
MJ: For sure. Winning the Super Bowl and being the top-rated D-tackle helped. Denver offered me five years for $45 million. Jacksonville came with six years for $90 million. I took Jacksonville. Three years later, I got cut—that’s the business—but I still made $45 million, then two years for $20 million in Philly, and one year for $10 million in Cleveland.
EV: How important is guaranteed money?
MJ: Huge. We risk our lives every play, yet only about 10% of players get big guaranteed deals. The other 90% are fighting for jobs, getting cut, signed, cut again. It’s tough.
EV: What about player benefits?
MJ: The way my body feels, I feel 55. Guaranteed money helps when those medical bills come in. The NFL and NFLPA have good benefits—but you’ve got to qualify. You usually need three credited seasons, and you get five years of Cigna coverage after your last snap. But the injuries show up later. That’s part of why I started The Care League.
We help players understand and use their benefits: workers’ comp, line-of-duty and the Gene Upshaw HRA fund. With 10 years played, I have about $300,000 available for medical costs. I want to help guys bridge that gap between the locker room and real life.
EV: How did The Care League come to life?
MJ: When I first retired, I lived like Pepe Le Pew—on the beach, enjoying life. But after about a year and a half, I sat down and started looking at my benefits and coverage. I realized I didn’t even know what a PPO or HMO was. I was 32, trying to figure out life on my own.
I was driving a Rolls-Royce past people struggling, and it didn’t feel right. That’s when The Care League came to life—to help guys transition, get care quickly and feel supported like they did when playing.
When I needed a doctor for back pain, the earliest appointment was two months out. I was used to walking into the training room the next day and getting an MRI. That’s when I knew something had to change.
Through The Care League, we’ve partnered with Powerhaus Sports Agency, representing athletes from high school NIL deals through the pros. Together, we help their clients with mentorship, access to care and guidance on handling newfound wealth.
EV: Is The Care League nationwide?
MJ: Yes. We’ve partnered with telemedicine and mental wellness providers so guys can build real relationships and get consistent care—no matter where they are. The Care League isn’t just about healthcare either—it’s about lifestyle too. We help members live better, not just feel better. Whether that means coordinating a last-minute trip, booking recovery and spa sessions after a tough week, getting access to exclusive events or simply making sure your family’s day-to-day runs smoothly—we take care of it. We bring that locker room level of support to every part of your life.
EV: You’re doing great things with The Care League, Malik. Appreciate the time today.
