5 Worst Investments Pro Athletes Ever Made

worst investments - 5 Worst Investments Pro Athletes Ever Made

Source: Jeff Kern via Flickr

All too often, we read about millionaire pro athletes that have blown through their fortunes buying expensive cars and treating huge posses to lavish nights out on the town.


Unfortunately, a number of pro athletes have lost their money another way: bad investments.

Be it businesses gone bust, bad steps into unfamiliar markets or even just a bad decision (or a string of them), there are a lot of ways to lose a lot of money. Just because these people have made millions because of their athletic prowess, it doesn’t make them immune to many of the same pitfalls as other investors.

Here’s a look at five of the worst investments pro athletes ever made.

Pro Athletes’ Worst Investments: Curt Schilling’s Video Game Fail

Pro Athletes' Worst Investments: Curt Schilling's Video Game Fail

During Curt Schilling’s 19-year career in the MLB, he earned nearly $115 million.

Instead of investing his savings in a low-risk mutual fund or other safe investment, he founded and funded the launch of one of the worst investments in video game history: 38 Studios. Schilling sank $50 million of his own money into his vision of building a billion-dollar video game company.

To make matters worse, the state of Rhode Island gave 38 Studios $75 million in loans. The company released its only game, Kingdoms of Amalur: Reckoning, back in 2012. A few months later, the company declared Chapter 7 bankruptcy.

Schilling reportedly never took a salary while serving as the CEO of 38 Studios and lost every cent of his $50 million.

Pro Athletes’ Worst Investments: Lenny Dykstra’s Bad Choices

Pro Athletes' Worst Investments: Lenny Dykstra's Bad Choices

It’s one thing for a pro athlete to get swindled by nefarious financial advisors, but former MLB player Lenny Dykstra actually became a financial advisor himself.

CNBC’s Jim Cramer hired Dykstra in 2005 to publish a premium investment advice column on TheStreet.com. Subscribers paid $999.95/year to get his trading advice. Cramer says that Dykstra had a good instinct for stock picks.

“Lenny was doing really well, coming up with some terrific winning ideas,” Cramer once said of Dykstra.

Unfortunately, Dykstra became extremely reckless and made a string of bad investments. He sunk millions of dollars into a private jet, the publication of a glossy financial advice magazine for professional athletes and huge real estate investments like Wayne Gretzky’s $18.5 million home.

Dykstra was sentenced to three years in prison in 2012 for grand theft auto and providing false financial statements.

Pro Athletes’ Worst Investments: Mark Brunell’s Real Estate Timing

Pro Athletes' Worst Investments: Mark Brunell's Real Estate Timing

Former NFL quarterback Mark Brunell was one of many victims of the real estate downturn in 2007. However, few people lost as much as Brunell did.

During the last 10 years of his playing career, Brunell earned $52 million. After retirement, Brunell and former teammates formed real estate partnership — Champion LLC — which made some of the worst investments possible.

“The timing of the group’s real estate acquisitions at the height of the real estate market, in hindsight, clearly was not good,” Brunell said of the partnership after filing for bankruptcy in 2010.

Pro Athletes’ Worst Investments: Scottie Pippen’s Jet That Couldn’t Fly

Pro Athletes' Worst Investments: Scottie Pippen's Jet That Couldn't Fly

Michael Jordan’s right-hand man played a critical role in the Bulls’ six NBA championships throughout the 90s. However, off the court, Scottie Pippen made some of the worst investments imaginable.

Pippen bought a $4.3 million Gulfstream private jet back in 2002. Incredibly, he reportedly didn’t know at the time the jet needed $1 million in repairs before it could even fly.

The grounded private jet may have been one of Pippen’s dumbest investments, but it wasn’t his most costly. He reportedly lost $27 million in the real estate market as well.

Pro Athletes’ Worst Investments: Johnny Unitas’ String Of Bad Investments


Johnny Unitas’ investing career began early when he opened Maryland’s first tenpin bowling alley back in 1961. Within three years, the bowling alley declared bankruptcy and Unitas lost his relatively modest $21,666 stake.

Unitas was later part of a massive Florida real estate partnership that acquired 788 acres of land, a crab and catfish supply company and a hotel and restaurant in south Florida. The partnership soon fell apart.

The final blow to Unitas’ investing career came in 1984 when he purchased chip maker National Circuits Inc. for $3.5 million. After years of mismanagement, National ended up one of the worst investments of his career. National’s assets were sold to a rival company for $1 million in 1990, and Unitas was forced into bankruptcy.

As of this writing, Wayne Duggan did not hold a position in any of the aforementioned securities.

Article printed from InvestorPlace Media, https://investorplace.com/2016/09/worst-investments-pro-athletes/.

©2022 InvestorPlace Media, LLC