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Notable Investments Made by NFL Players Throughout the Years

Joburg Admin / August 26, 2025

Professional athletes across all sports have increasingly recognized that their athletic careers are short, and their earning potential is finite. In days gone by, football, basketball, and soccer players might have planned for their future by opening a bar or a restaurant.

Today, wages are so high and earning potential so varied that athletes are instead looking at more eye-catching and glamorous ways to invest their money and prepare for their future. Just as the NFL spreads can be unpredictable, so can investing, meaning not every story finishes with a happy ending.

In this article, we look at some of the most high-profile and intriguing investments made by NFL players, with varying degrees of success. Read on to find out about dodgy casino deals, an incredible real estate venture, and a third-division English soccer team…

Dermontti Dawson – Real Estate Loser

60-year-old Dermontti Dawson spent 12 years playing for the Pittsburgh Steelers, where he racked up a series of awards and accolades. He was named in 6 First-team All-Pros and 7 Pro Bowls and in the NFL 1990s All-Decade Team before being inducted into the Pro Football Hall of Fame in 2012.

Unsurprisingly, Dawson was remunerated well for his services to the Steelers, with his highest-paying contract seeing him take home $4.2 million a year at one point. In 2010, though, he was declared bankrupt, with bills totalling over $70 million and assets valued at just $1.42 million.

The housing crash of 2008 saw the majority of his real estate investments—of which he had no controlling stake—go bust, ultimately leading to his own financial ruin.

https://www.youtube.com/watch?v=IZyp3PD7xHw

(Dermontti Dawson isn’t the only NFL player who has lost a fortune after retiring.)

Roger Staubach – Real Estate Winner

‘Captain America’, as he was fondly known as quarterback at the world-famous Dallas Cowboys has the Midas touch when it comes to both football and investing. During his professional career he won 2 Super Bowls and far too many individual awards and accolades to mentions.

Unfortunately for Staubach, he played at a time when the money on offer to football players was a fraction of what it is today. If he had played in the modern game, he could have lived off the interest on his salary alone.

Staubach would probably say now that his $25,000 a year salary during his playing career was a blessing in disguise, as it made him seriously plan for retirement. Two years before retiring, the Cowboys man founded The Staubach Company, a real estate firm focused on corporate tenants rather than building owners.

31 years on from that in 2008, Staubach sold the company for $613 million which, on a ROI basis, surely makes him the most successful NFL investor of all-time.

Tom Brady – Birmingham Bluenose

While Tom Brady has made several investments that have returned him millions of dollars, the most interesting by far has been his cash injection into English soccer side Birmingham City. Two years ago, just six months after retiring from professional football, Brady bought a 3.3% stake in the then-Champions League side.

His involvement with the club helped raise Birmingham City's profile overseas, but unlike other high-profile investors, Rob McElhenney and Ryan Reynolds, Brady’s first taste of English football failed.

At the end of his first season with Birmingham, the club was relegated to the English third tier. The sacking of manager Wayne Rooney—perhaps under Brady's guidance—along with a huge wave of investment, saw the club return to the second tier the following season after winning the league title with a record number of points.

It’s unclear how much involvement Brady will have in the club going forward, but along with the aforementioned McElhenney, Reynolds, and Snoop Dog, who is on the board at Swansea City, English football is beginning to have a distinctly American feel.

https://www.youtube.com/watch?v=MLxYN1E8FNU

(Tom Brady wasn’t a fan of Birmingham City manager Wayne Rooney.)

In Summary

In years gone by, it made sense for football players to look to the future and plan for their retirement. Nowadays, the salaries offered to players throughout their careers should be enough to sustain them for the rest of their lives.

That doesn’t make them immune to falling into the tempting world of investing, where following in Roger Staubach's footsteps is hard, but going down the same path as Dermontti Dawson is, unfortunately, all too easy.

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