Baseball might be America’s pastime, but even legends of the game haven’t been immune to financial curveballs. From questionable investments to lavish lifestyles and messy legal battles, these stars learned the hard way that hitting home runs doesn’t guarantee a lifetime of financial security.
This list dives into the baseball icons who made millions on the field, only to watch it slip away off the field. Whether it was poor planning or bad luck, these stories are cautionary tales wrapped in pinstripes.
10. Denny McLain
Once a Cy Young winner and the last pitcher to win 30 games in a season, McLain had the world at his feet. Unfortunately, he fell into serious trouble with gambling, prison time, and failed ventures that wiped out his wealth.
9. Jack Clark
Clark had a powerful bat and a big league salary to match, but he reportedly blew through millions thanks to spending on luxury cars and mismanaged funds. His financial collapse led to a very public bankruptcy.
8. Darryl Strawberry
Strawberry’s career was filled with highlight-reel moments—and off-field turmoil. Legal issues, drug problems, and unpaid taxes drained his finances over the years.
7. Jose Canseco
One of the most controversial sluggers of his era, Canseco made a fortune during his playing days. But a mix of divorces, legal issues, and unsuccessful business deals eventually left him in financial ruin.
6. Lenny Dykstra
Nicknamed “Nails” for his gritty play, Dykstra’s post-baseball life spiraled into lawsuits, jail time, and a mountain of debt. He went from Wall Street wannabe to bankruptcy court regular.
5. Bobby Bonilla
Bonilla may still get a check every July, but the way his money was managed raised more than a few eyebrows. Despite his infamous deferred payments, he had several financial hiccups, including lawsuits and investment blunders.
4. Curt Schilling
Schilling was a postseason hero, but his attempt to launch a video game company turned into a massive flop. He lost tens of millions and dragged Rhode Island taxpayers along for the ride.
Read more: 15 Retired NFL Stars Who Are Way Less Rich Than You’d Think
3. Dwight Gooden
Like his former teammate Strawberry, Gooden’s talent couldn’t shield him from personal demons. Drug issues, legal troubles, and poor financial decisions cost him more than just money.
Read more: 14 NFL Stars Who Were Very Smart With Their Money
2. Pete Rose
Baseball’s all-time hit king saw his legacy and finances take a beating thanks to gambling scandals. He’s spent years trying to recover both his image and his bank account.
Read more: 15 NFL Stars Who Blew a Fortune Before 40
1. Bernie Madoff’s Mets Victims
This one’s a curveball—because it wasn’t one player, but several Mets icons, including the Wilpon ownership group, who got caught in Bernie Madoff’s Ponzi scheme. The fallout left the franchise financially gutted and scrambling for years.
