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8 Huge Financial Meltdowns by Major League Baseball Players

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It’s not easy being rich if you are big league ballplayer, at least judging by the list of athletes who have declared bankruptcy.

The reasons vary – from bad advisors to profligate spending by young men ill equipped to be entrusted with millions of dollars. Even some of the game’s all-time greats have fallen on hard times.

In the past, we’ve looked at other athletes who frittered away their millions. Baseball player Lenny Dykstra was notable for his business of offering financial advice to other wealthy athletes.

(Related: Top 10 Worst Financial Meltdowns by Athletes and 8 of the Worst Financial Meltdowns by Athletes)

With the World Series starting this week, we decided it was time to look at 8 Huge Financial Meltdowns by Major Leaguers.

Johnny Evers with the Cubs, circa 1910.

8. Johnny Evers

Lifetime Earnings: $53,950

Evers’ name will live on as part of the Cubs infield of Tinkers to Evers to Chance, but we thought it was interesting that such an iconic player from baseball’s earliest day couldn’t escape bankruptcy. (So early, in fact that the Cubs were regulars in the World Series.) Evers retired in 1918, when that amount was worth more than $850,000 when adjusted for inflation. Of course, most ballplayers of that era had to work to provide for their families after they retired. Evers was no exception, operating a sporting goods store in Albany, New York. He filed for bankruptcy in 1936, but was able to keep the store and pass it to his descendants who kept in going into the 1990s.

Former Minnesota Twins Harmon Killebrew. (Photo: AP)

7. Harmon Killebrew

Lifetime Earnings: $825,000

Playing in an era before the money got really big, Killebrew nonetheless did vey well for himself as he slugged more than 500 home runs for the Minnesota Twins on his way to the Hall of Fame. Unfortunately, the man who by all accounts was decent and honorable wasn’t good at making financial decisions. Loans from four banks and Twins owner Calvin Griffith, as well as one co-signed by baseball star Reggie Jackson, left Killebrew in the red when a car dealership and car leasing business failed. Unable to make payments on his house, “Killer” as he was known, filed for bankruptcy in 1989, vowing to make good on his debts.

San Francisco Giants Hall of Famer Gaylord Perry. (Photo: AP)

6. Gaylord Perry

Lifetime earnings: $1.6 million

Perry was famous for his 300 wins and admitting that he threw a spitball, even calling his autobiography “Me and the Spitter.” By athlete financial meltdown standards, Perry’s bankruptcy was relatively minor. He lost more than 400 acres of farmland he owned for 15 years to foreclosure in 1989. Perry, for his part, says he was going to give it up anyway. At the time, six years after his Hall of Fame 22-year career ended, he was mourning the loss of his wife in a car accident. Perry coached college baseball until he retired.

Former Philadelphia Phillies' Scott Eyre. (Photo: AP)

5. Scott Eyre

Lifetime Earnings: $17 million

Eyre is probably the least known of the players on our list, having toiled as a relief pitcher for several teams for 13 seasons ending in 2009. Still, with salaries exploding he managed to rake in a good amount of dough. Eyre had his assets frozen as his career neared its end because he invested his money with wealth manager Robert Allen Stanford, who was running a Ponzi scheme. Things were so bad for Eyre that the Phillies agreed to give him an advance on his 2009 salary so he could keep a roof over his head.

Jack Clark, also known as "Jack the Ripper" is a former MLB player. (Photo: AP)

4. Jack Clark

Lifetime Earnings: $20 million

“Jack the Ripper” as he was known for the prodigious power that helped him belt 340 home runs for the San Francisco Giants, St. Louis Cardinals and New York Yankees was riding high with a huge contract from the Boston Red Sox in 1992. That’s when his spending habits – 18 cars including a Ferrari and a Rolls Royce, a huge credit card bill and a multimillion dollar home – caught up to him. He declared bankruptcy, listing $6.7 million in debts, as his career came to an end. Clark was quoted as saying that while he accepted some of the blame, he was a victim of a financial team that did not give him good advice.

Jose Canseco, former MLB outfielder. (Photo: AP)

3. Jose Canseco

Lifetime Earnings: $45 million

Canseco first came to prominence as part of the “Bash Brothers” with Mark McGwire on the Oakland A’s. Then he blew the whistle on the use of steroids in the game. No one believed him at first, or wanted to believe him, but his accusations of rampant use started a cascade that led to a black eye for some the sport’s biggest stars and baseball itself. In 2012, Canseco filed for bankruptcy listing debts of about $1.7 million. In an interview he explained that his problems stemmed in part because the more someone earns the more they have to spend on family and friends. His formula was that he spends half on them, half on himself and then don’t get him started on the cost of living increase. And don’t get us started on his failure to pay taxes for several years or his complaint that he felt enslaved because of fines, penalties and wage garnishments over that small matter.

Tony Gwynn at the 2011 Baseball Hall of Fame induction parade.

2. Tony Gwynn

Lifetime Earnings: $47 million

Tony Gwynn was a great hitter who flirted with becoming the first to hit .400 since Ted Williams in 1941 and was considered one of the most likeable players in the sport. Unfortunately, taking care of his loot was not his strong suit. In 1987 while still playing, Gwynn was the victim of his agent who Gwynn said used him to co-sign loans that went into default. That caused Gwynn to file for bankruptcy claiming debts of about $1.6 million. Then in 2012, it was reported that he owed $400,000 in back taxes for three separate years. Gwynn died of cancer in 2014.

Former Boston Red Sox pitcher Curt Schilling. (Photo: AP)

1. Curt Schilling

Lifetime Earnings: $105 million

Schilling had an amazing career topped by the sight of his bloody sock as he pitched the Red Sox to a victory over the New York Yankees in Game 6 of the 2004 American League Championship Series. That win drew the series even and helped the Sox win their first World Series since 1918. His run of good luck ended with his foray into video gaming when his 38 Studios (named for his uniform number) famously tanked after getting loans worth $75 million from the state of Rhode Island. Schilling personally guaranteed the loans and invested $50 million of his own. And the money lost by Rhode Island caused mega problems for the state’s budget.

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