Despite being known for making millions of dollars, many Major League Baseball players can lose the money in a heartbeat, whether it is poor investments, wild spending, or the people around these Major Leaguers hoping to get a handout from their friends or family.
A player works their whole life to get to the point where they can live comfortably, losing that money can derail their entire post-retirement plans.
Many Hall of Famers, Most Valuable Players, Cy Young winners, former All-Stars, and World Series Champions have fallen victim to bankruptcy, homelessness, and even prison time due to financial issues.
Here are the Major League Baseball players that went broke.
Bill Buckner
Bill Buckner could not catch a break! One of the biggest blunders in sports history was part of the Boston Red Sox in 1986, when he made an erroneous error in letting a ground ball go through his legs vs. the New York Mets. His post-playing career was not much better.
A batting champion and All-Star in his career. In 2008, the car dealership he was a partial owner of in Idaho went out of business forcing him to file for bankruptcy.
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Curt Schilling
Known for his clutch moments in the 2001 and 2004 postseasons. Curt Schilling was known as a big game player during his days in the Major Leagues. He won both a World Series Most Valuable Player award in 2001 and a National League Championship Series Most Valuable Player award in 1993.
He is the owner of three World Series rings, and in 2006 created a video game company 38 Studios in 2006, the company received a $75 million loan in 2010. They bounced a loan payment check laid off their entire staff and filed for bankruptcy.
Rollie Fingers
Rollie Fingers became one of the greatest relief pitchers of his era. He was a three-time World Series champion, the 1974 World Series Most Valuable Player, the 1981 American League Most Valuable Player, and the 1981 Cy Young winner. He has had his jersey number retired by two franchises, the Oakland Athletics, and the Milwaukee Brewers.
He entered the Hall of Fame in 1992. He put himself in $4.5 million in debt. He filed for bankruptcy in 1989. He invested in Egyptian Arabian horses, wind turbines, a pistachio farm, and an apartment-flipping scam. He filed for bankruptcy in 1989.
Tony Gwynn
The best pure hitter of his generation, Tony Gwynn, was an eight-time batting champion who batted .338 and finished his career with 3141 hits. He was a 15-time All-Star and appeared in two World Series with the Sandiego Padres. Known as “Mr. Padre” by the fans, he spent all 20 seasons with the organization.
Early in his career, Gwynn filed for bankruptcy. He faced liabilities of over $1.1 million due to poor financial decisions. He was billed in 2003, 2007, and 2009 for more than $400,000 of unpaid income taxes.
Pete Rose
The all-time leader in hits, Pete Rose, could not catch a break after his historic career was over. He was banned from baseball for life after being caught betting on games.
He did not claim income from selling autographs and memorabilia, earning him two counts of tax evasion, and he was fined $50,000 on top of the $366,041 that he owed. The three-time World Series champion and 1975 Most Valuable Player was sent to prison for five months due to his tax evasion issues and served that time in Marion, Illinois.
Denny McLain
The last player to ever win 30 games in a season. Denny McLain won the American League Most Valuable Player Award, two Cy Youngs, was a three-time All-Star, and was a member of the 1968 Detroit Tigers that went on to win the World Series. He gambled in his spare time, routinely making bets on horse racing that led to his debts.
There have been claims that he was injured due to punishment for not paying his gambling debts. He was also suspended for his gambling issues in Major League Baseball. McLain filed for bankruptcy after his career was finished.
Lenny Dykstra
Lenny Dykstra was a three-time All-Star and a part of the 1986 New York Mets that won the World Series. Originally a success after his playing career was over. He sold the car wash that he owned in California in 2007. He then purchased Wayne Gretzky’s house to flip it but was unsuccessful.
In 2008, he started a high-end jet Charter company. It was soon revealed that Dykstra was committing credit card fraud, bouncing checks and lawsuits against him. In 2012, he spent over six months in prison and was ordered to do 500 hours of community service.
Harmon Killebrew
The Hall of Famer Harmon Killebrew was a six-time home run leader, 13-time All-Star, and the 1969 American League Most Valuable Player. He spent most of his career with the Minnesota Twins and arguably their best player of all time. Killebrew fell victim to fraud and had two failed car companies.
He lost his home in 1988 and was $700,000 in debt. He owed money to multiple banks, former teammates, and other Major League ball players.
Gaylord Perry
Gaylord Perry became a two-time Cy Young winner and a five-time All-Star. Known for doctoring baseballs using spitballs, Elected to the Hall of Fame in 1991. In 1986 Perry declared
bankruptcy after amassing $1.2 million in debt to $1.1 million in assets. His 400-acre peanut, soybean, tobacco, and corn farm in eastern North Carolina failed to turn a profit.
Steve Howe
A former All-Star, National League Rookie of the Year, and World Series Champion. He followed it all up by declaring bankruptcy in 1983. He had $340,000 in debt and checked himself into rehab for alcohol and drug abuse. He was given a lifetime ban in 1992 and successfully appealed it and retired in 1996. He died at age 46 after a drug related car accident took his life.
