15 NFL Legends Who Tried Business Ventures That Totally Flopped

For every touchdown scored or Super Bowl won, there’s an off-field gamble that didn’t quite pan out. While some NFL legends have successfully transitioned to the boardroom, others learned the hard way that business success isn’t guaranteed, no matter how many Pro Bowls you’ve made.

From frozen foods to failed car washes, these 15 former NFL stars launched ventures that either lost steam, lost money, or just plain didn’t make sense. Here’s a look at the business moves that didn’t live up to the hype.

15. Clinton Portis

Aug 21, 2010; Landover, MD, USA; Washington Redskins running back Clinton Portis warms up before the start of a preseason game against the Baltimore Ravens at FedEx FIeld. Mandatory Credit: James Lang-Imagn Images
James Lang-Imagn Images

Clinton Portis invested heavily with a financial advisor who turned out to be, let’s say, not the most qualified. His business efforts ended with lawsuits, bankruptcy filings, and a reminder that flashy suits don’t equal financial smarts.

14. Deion Sanders

Sep 11, 1997; Irving, TX, USA; FILE PHOTO: Dallas Cowboys defensive back Deion Sanders (21) celebrating as he scores a touchdown on an interception against the Chicago Bears at Texas Stadium. Mandatory Credit: James D. Smith-USA TODAY Sports
James D. Smith-Imagn Images

Prime Time tried launching a charter school network, and it didn’t exactly go according to plan. The schools faced financial issues, mismanagement allegations, and ultimately shut down.

13. Vince Young

Aug 29, 2013; Kansas City, MO, USA; Green Bay Packers quarterback Vince Young (13) looks to the sidelines during the second half of the game against the Kansas City Chiefs at Arrowhead Stadium. The Chiefs won 30-8. Mandatory Credit: Denny Medley-Imagn Images
Denny Medley-Imagn Images

Vince Young opened a steakhouse in Houston, and it shut down faster than his NFL comeback attempts. Legal battles and unpaid bills piled up, turning his business dream into a cautionary tale.

12. Bernie Kosar

Jan 8, 1995; San Diego, CA, USA; FILE PHOTO; Miami Dolphins quarterback Bernie Kosar (19) on the sidelines against the San Diego Chargers during the 1994 AFC Divisional playoffs at Jack Murphy Stadium. Mandatory Credit: Peter Brouillet-USA TODAY NETWORK
Peter Brouillet-Imagn Images

Bernie Kosar tried everything from restaurants to car dealerships, but most of it ended in financial ruin. He even declared bankruptcy, with over $18 million in debt and a business portfolio that looked more like a clearance rack.

11. Jamal Lewis

October 19, 2008; Landover, MD, USA; Cleveland Browns running back Jamal Lewis (31) is tackled by Washington Redskins safety Chris Horton (48) and safety LaRon Landry (30) in the third quarter at FedEx Field. The Redskins won 14-11. Mandatory Credit: Geoff Burke-Imagn Images
Geoff Burke-Imagn Images

Jamal Lewis got into trucking and real estate development, but the ventures hit a wall. He ended up filing for bankruptcy after his post-football investments couldn’t keep up with the bills.

10. Terrell Owens

Sep 12, 2010; Foxboro, MA, USA; Cincinnati Bengals wide receiver Terrell Owens (81) looks to the bench after missing a pass during the second half against the New England Patriots at Gillette Stadium. The Patriots defeated the Bengals 38-24. Mandatory Credit: David Butler II-Imagn Images
David Butler II-Imagn Images

T.O. didn’t just drop passes—he dropped millions on bad investments and shady financial advisors. His business ventures were so unsuccessful, he ended up going public about being nearly broke.

9. Chris McAlister

Aug 4, 2007; Baltimore, MD, USA; Baltimore Ravens cornerback Chris McAlister during a scrimmage against the Washington Redskins at M&T Bank Stadium in Baltimore, MD. Mandatory Credit: James Lang-Imagn Images Copyright © James Lang
James Lang-Imagn Images

Chris McAlister once had a $50 million NFL contract, but post-retirement life hit him hard. He admitted to being broke and living with his parents after a string of failed business decisions and financial missteps.

8. Michael Vick

Jan 6, 2002; St. Louis, MO, USA; FILE PHOTO; Atlanta Falcons quarterback Michael Vick (7) in action against the St. Louis Rams at the Edward Jones Dome. Mandatory Credit: James D. Smith-Imagn Images
James D. Smith-Imagn Images

Vick’s name was once tied to a sporting goods line and other endorsement ventures, but they all crumbled under the weight of his legal troubles. His off-field business potential never had a real chance to grow.

7. Andre Rison

Dec 7, 1997; Kansas City, MO, USA; FILE PHOTO; Kansas City Chiefs receiver receiver Andre Rison (89) in action against the Oakland Raiders at Arrowhead Stadium. Mandatory Credit: James D. Smith-Imagn Images
James D. Smith-Imagn Images

“Bad Moon” Rison lived up to his nickname with some wildly reckless spending and terrible investments. One of his worst moves? Backing a music label that never took off and burned through his cash.

6. Warren Sapp

Nov 11, 2013; Tampa, FL, USA; Tampa Bay Buccaneers hall of famer Warren Sapp talks as he is inducted into the Ring of Honor at halftime against the Miami Dolphins at Raymond James Stadium. Mandatory Credit: Kim Klement-Imagn Images
Kim Klement-Imagn Images

Warren Sapp was a beast on the field, but his business choices were a mess. After investing in failed real estate deals and blowing millions, he filed for bankruptcy, claiming he couldn’t even afford a pair of shoes.

5. Fred Taylor

Oct 27, 2019; Jacksonville, FL, USA; Ex-Jacksonville Jaguars running back Fred Taylor (white shirt) looks on prior to the game between the Jacksonville Jaguars and the New York Jets at TIAA Bank Field. Mandatory Credit: Douglas DeFelice-Imagn Images
Douglas DeFelice-Imagn Images

Fred Taylor lost millions through shady financial management and tried launching a marketing firm that didn’t take off. He’s since spoken openly about the hard lessons learned from putting trust in the wrong people.

4. Ray Rice

Jan 12, 2013; Denver, CO, USA; Baltimore Ravens running back Ray Rice (27) runs the ball in the first half against the Denver Broncos during the AFC divisional round playoff game at Sports Authority Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
Mark J. Rebilas-Imagn Images

After his NFL career ended, Rice made attempts to rebrand through business ventures, including trying to get into sports management. But public backlash and lack of interest from partners shut those doors quickly.

3. Mark Brunell

Oct 3, 2004; Cleveland, OH, USA;Washington Redskins #8 Mark Brunell talks with head coach Joe Gibbs on the sidelines at Cleveland Browns Stadium. The Browns beat the Redskins 17-13. Mandatory Credit: Photo by Matthew Emmons-Imagn Images (©) Copyright 2004 by Matthew Emmons
Matthew Emmons-Imagn Images

Brunell was once one of the NFL’s top quarterbacks—and one of its worst businessmen. He invested in fast food franchises, real estate, and a chain of Whataburgers, only to end up filing for bankruptcy.

Read More: Top 7 NFL Stars Whose Accounts Didn’t Survive Retirement

2. Lawrence Taylor

Lawrence Taylor is a two-time Super Bowl champion, a nine-time First Team All-Pro selection, the NFL MVP (1986) and a 3-time NFL Defensive Player of the Year (1981, 1982, 1986). Xxx Bw Lawrence Taylor 0202 S Fbn Usa Ny
Robert Deutsch, USA TODAY, USA TODAY via Imagn Content Services, LLC

LT’s post-career life has been filled with legal troubles and business stumbles. From failed ventures to bad endorsements, his financial decisions have been as chaotic as his playing style.

Read More: 14 Former NFL Stars Who Got Humbled by Life After Football

1. Johnny Unitas

Sep 1972; Unknown location, USA; FILE PHOTO; Baltimore Colts quarterback Johnny Unitas (19) in action during the 1972 season. Mandatory Credit: Tony Tomsic-USA TODAY NETWORK
Tony Tomsic-Imagn Images

Yes, even Johnny U took a shot at business and missed. His electronics company went under in spectacular fashion, leaving him in deep debt despite his iconic status in the sport.

Read More: 10 Times NFL Stars Filed For Bankruptcy

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