MLB Players Who Went From Riches To Rags

Athletes | 2/26/20

It’s no secret to anyone that professional athletes make a lot of money. And baseball players make even more than most because their contracts are fully guaranteed and careers are often longer due to less injury risk.

Still, there are always plenty of people looking to take advantage of these players. And there are always addictions and demons that could cost players big bucks. Below are some of the most famous baseball players who have squandered their fortunes.

Lenny Dykstra

lenny dykstra mlb star
Focus on Sport/Getty Images
Focus on Sport/Getty Images

Lenny Dykstra has become the poster child for players who lost everything. The center fielders starred for the famous 1986 Mets team, for whom he hit mutiple dramatic home runs. He later continued to star for the Philadelphia Phillies.

After his career, Dykstra opened multiple successful car washes in Southern California. He also made a number of seemingly smart investments. It all fell apart in 2011 when he was arrested for bankruptcy fraud and spent more than six years in prison.

Curt Schilling

curt schilling mlb pitcher
G Fiume/Getty Images
G Fiume/Getty Images

Becoming a star with the Phillies in the late ’90s, Curt Schilling had a Hall of Fame worthy baseball career. He formed one of the great 1-2 punches of all-time with Randy Johnson on the 2001 Diamondbacks. He was then an integral piece of the Red Sox team that broke the Curse of the Bambino.

His post-playing career has not gone so well. Schilling founded a video game company that almost immediately folded. He was also fired from ESPN after making multiple incendiary comments over Twitter.

Jack Clark

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Focus on Sport/Getty Images
Focus on Sport/Getty Images

Jack Clark was a feared slugger for a number of teams in the ’70s and ’80s, most notably the Giants and the Cardinals. The first baseman was a four-time All-Star and also won two Silver Slugger awards.

Clark, who hit 340 homers in the majors, was much less successful off the field. Thanks to an unquenchable appetite for luxury cars, the longball hitter lost all his money. His 1992 bankruptcy filing noted that he owned 18 high-end vehicles.

Rollie Fingers

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Rich Pilling/MLB Photos via Getty Images
Rich Pilling/MLB Photos via Getty Images

Oakland Athletics pitcher Rollie Fingers was remembered for two things. For one, he had an incredible mustache that only a really confident guy could pull off. For another, he was a dominant reliever more than capable of mowing down opposing hitters.

He made some very interesting and very poor investments following his career. The businesses he put billions into included wind turbines, middle eastern horses and pistachio farms. The hurler was inducted into the Baseball Hall of Fame in 1992.

Cecil Fielder

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Sporting News via Getty Images via Getty Images
Sporting News via Getty Images via Getty Images

For a large portion of the early 1990s, Cecil Fielder was the most feared player in the game. The Tigers first baseman returned from Japan in 1990 and smacked 52 home runs. In his career, he hit 319 taters.

Unfortunately for the slugger, who made an estimated $46 million during his playing career, he also had a gambling problem. At one point, Fielder lost $588,000 in one weekend in Atlantic City and was sued y the casino.

Scott Eyre

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Jared Wickerham/Getty Images
Jared Wickerham/Getty Images

There’s plenty of money to be made if you’re a productive lefty out of the bullpen. And Scott Eyre made a nice career in this role, making around $17 million during his career which culminated in a World Series win with the 2008 Phillies.

Sometimes, however, players get caught up with predatory investors. Unfortunately for Eyre, he invested his money with Allen Stanford who was running a major Ponzi scheme. By the end of his career, Eyre was broke and taking advances on his paychecks.

Rick Wise

Rick-Wise-mlb
Via mlb.com
Via mlb.com

Rick Wise was a very good pitcher in the Major Leagues for a number of years. During his playing career, he was also known as one of the better hitting pitchers in the league, slugging 15 homers before retiring.

Players who last 18 years in the bigs often have a fair amount of money saved at the end. That wasn’t true for Wise, though, as he was deceived by a crooked agent named LaRue Harcourt who invested his money poorly. After paying back taxes to the IRS Wise essentially had nothing left.

Wally Backman

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Focus on Sport/Getty Images
Focus on Sport/Getty Images

Backman is the second member of the famed 1986 Mets to appear on the list. The second baseman, who hit .320 in ’86, played nine seasons for the Mets and five seasons for four other teams.

After his playing career, he became a successful minor league manager and was hired by the Arizona Diamondbacks. A domestic violence arrest derailed that shot though. And Backman later filed for bankruptcy as he didn’t have the money to pay back a number of creditors.

Bill Buckner

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Bettmann/Getty Imapges
Bettmann/Getty Imapges

Most baseball fans remember Bill Buckner as the unfortunate player who muffed an easy play during the World Series. Hard-core fans, though, know that Bucker had a fantastic career and was playing that game on very injured knees.

The line-drive hitting first baseman got his start as an outfielder in the Dodgers organization and went on to play for over 20 years. He then owned a car dealership in Idaho that went out of business. Buckner later had to file for bankruptcy.

Graig Nettles

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Michael Stewart/WireImage
Michael Stewart/WireImage

The New York Yankees team of the 1970s was brash and successful and full of big personalities. One of the biggest personalities was big slugging and smooth fielding third baseman Graig Nettles.

The long-time Yankee made the All-Star game six times during his career that also saw him win two Gold Gloves and two World Series Championships. He also had some terrible trouble with some financial investments. When he retired from the game in 1988, he was over $1 million in debt.

Tony Gwynn

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Focus On Sport/Getty Images
Focus On Sport/Getty Images

When people think about the greatest hitters of all-time, they mention guys like Rogers Hornsby, Ted Williams, and Tony Gwynn. Gwynn was an effortlessly excellent hitter who finished his career with a batting average of .338.

The left fielder played his entire Hall of Fame career in San Diego and made the All-Star team eight times. He also went over $1 million in debt thanks to bad investments. Gwynn was later diagnosed with parotid cancer and passed away in 2014.

Gaylord Perry

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MediaNews Group/Bay Area News via Getty Images
MediaNews Group/Bay Area News via Getty Images

During his career, Gaylord Perry was known for his attempts to doctor baseballs in whatever way possible. The spit-baller began his career with the San Francisco Giants and later played for another eight Major League teams.

The spitball worked quite well for Perry who made five All-Star teams and won two Cy Young Awards. He was named to the Hall of Fame in 1991. He had financial troubles post-career and ended up in bankruptcy court thanks to his failing North Carolina farm.

Denny McLain

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Mark Cunningham/MLB Photos via Getty Images
Mark Cunningham/MLB Photos via Getty Images

Denny McLain was considered to be maybe the best all-around pitcher in baseball during the late 1960s. The Detroit Tigers’ hurlers had one of the best seasons in MLB history when he won 31 games in 1968.

The pitcher, though, had significant problems with both investments and gambling. After his sixth season, the league suspended him over his gambling issues. When he came back from the suspension, he was not the same guy and retired penniless a few years later.

Pete Rose

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Joe Robbins/Getty Images
Joe Robbins/Getty Images

Pete Rose was one of the greatest players of all-time. During his career, he made a total of 17 All-Star teams and won three World Series along with the 1973 National League MVP. And of course, he smacked a record 4,256 hits.

But Rose was troubled off the field and for reasons beyond gambling. The Cincinnati Red also had issues with his taxes. He was required to pay back over $400,000 in back taxes and later served a short stint in prison.

Willie Aikens

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Focus on Sport via Getty Images
Focus on Sport via Getty Images

Willie Aikens was one of the top sluggers during the late 1970s and early 1980s. The outfielder, who played for three different teams, set a record during the 1980 World Series when he smacked two home runs in two separate games.

Unfortunately, the former Kansas City Royal had a substance problem that resulted in two long stints in prison following his career. Aikens’ story has a happy ending, though, as he got clean, apologized to fans and now works as a minor league instructor for the Royals.

Jose Canseco

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Kirby Lee/Getty Images
Kirby Lee/Getty Images

Jose Canseco was not only one of the best players of the 1980s he was also one of the coolest. The outfielder and his teammate, Mark McGwire, were known as the Bash Brothers and powered the Oakland A’s to three straight World Series appearances.

Canseco, who played 16 seasons in the majors and slugged 462 home runs, had some issues after his career was over. Thanks to costs associated with multiple divorces, the former Athletic ended up losing his house along with nearly $10 million.

Doc Gooden

doc gooden mlb star
Dave Kotinsky/Getty Images for Cantor Fitzgerald
Dave Kotinsky/Getty Images for Cantor Fitzgerald

Dwight Gooden was a baseball phenomenon from the day he first took the mound. The Mets hurler was the Rookie of the Year in 1984, won the National League Cy Young Award in ’85 and was a World Series Champion in 1986.

But, sadly, addiction spoiled what looked like a Hall of Fame career. Gooden was suspended multiple times during his 16-year career. The former Yankee still struggles with it today and it has cost him a fortune.

Harmon Killebrew

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Rich Pilling/ MLB via Getty Images
Rich Pilling/ MLB via Getty Images

The Minnesota Twins have a long and proud baseball tradition. There are a couple of choices for the greatest Twin of all time, but Harmon Killebrew is high up on the list. He played in Minnesota for 15 seasons and was inducted into the Hall of Fame in 1984.

Following his playing career, the 13-time All-Star worked as a broadcaster and invested in a number of businesses. A number of these businesses failed and Killlebrew went broke for years. He was later able to pull himself out of his troubles and passed away in 2011.

Chuck Knoblauch

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Andy Lyons /Allsport
Andy Lyons /Allsport

Chuck Knoblauch saw big league success almost immediately. Walking into a loaded Twins team, the second baseman was the American League Rookie of the Year in 1991. He was also a four-time All-Star and won four World Series Titles.

Knoblauch’s career had a strange end when he developed a case of the yips and could no longer throw the ball to first base. He’s had a troubling post-career as well. The former Twin and Yankee lost his money in divorces and had multiple arrests for domestic violence. After these arrests, the Twins reversed a decision to put him in the team’s Hall of Fame.

Steve Howe

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UNDATED: Steve Howe #57 of the Los Angeles Dodgers poses for a portrait. Howe played for the Dodgers from 1980-1985. (Photo by MLB via Getty Images)
UNDATED: Steve Howe #57 of the Los Angeles Dodgers poses for a portrait. Howe played for the Dodgers from 1980-1985. (Photo by MLB via Getty Images)

Steve Howe was a relief pitcher who dominated out of the bullpen from day one. During his first season, in 1980, he was named Rookie of the Year. In 1981, he closed out the World Series for the Dodgers and then made the All-Star team in ’82.

Howe had a serious battle with addiction, though, and was suspended from baseball on seven different occasions. The addiction issues also forced the lefty to declare bankruptcy. Howe was killed in a car accident in 2006.