Broke Baseball Players: 5 Hall-of-Famers Who Struck Out at Money Management

No matter what time of year it is, we’re devoutly loyal to our sports. Whether it’s hockey, football, basketball or baseball, we all look up to pro athletes for their competitiveness, team spirit, physical prowess and Olympian determination.

We also seem to take a strange curiosity in them when they make poor banking choices and, sometimes, fall flat broke. How can pro athletes have such great command of their athletic abilities but no command over their own earnings?

In honor of a new round of baseball Hall of Fame inductees this summer, let’s take a look at five all-star baseball Hall of Famers who showed us the right way to swing for the fences — and the wrong way to manage money.

The Baseball Finance Hall of Shame

5. Harmon Killebrew 

“Somewhere between fame and 50, Harmon Killebrew lost his way, his marriage and his financial security,” wrote Jay Weiner of the Minneapolis-St. Paul Star Tribune. That was in 1989, when retired slugger Killebrew’s legendary standing with Minnesota Twins fans would become tainted with details of debt, bankruptcy and more.

“Killer” killed any ball that came his way, and was a member of the famed 500 home run club (573, to be exact), with 2,086 career hits. But by the late 1980s, Killebrew was in grave debt. According to the Tribune, the Hall of Famer owed more than $700,000 to several banks and teammates, went into foreclosure on his $270,000 Oregon dream house, and endured the failure of his car dealership.

Though Killebrew bounced back through autograph signings before his death, he was forced to move back to his native Idaho and rented a modest condo during his financial troubles.

4. Tony Gwynn

manage moneyTony Gwynn was and will always be known as “Mr. Padre” for spending his entire 29-year career with the San Diego Padres, where he amassed 3,141 hits with a .338 batting average.

But Gwynn’s financial woes started long before his Hall of Fame induction in 2007. In fact, they began just five years after he began playing pro ball. In 1987, Gwynn filed for Chapter 7 bankruptcy, claiming debts of more than $1.1 million, and assets of nearly half that.

Gwynn had gotten into some money management tangles with his then-agent, and while it didn’t put a dent in his ball playing, it’s still an infamous part of Mr. Padre’s history.

Photo credit:

3. Gaylord Perry

The father of the spitball made a controversial entry into the Hall of Fame in 1991 after years of accusations that Perry frequently doctored the ball on his way to 3,534 career strikeouts. He wasn’t considered one of the most honest pitchers in the game, but it wasn’t until his post-baseball years that an honest living turned out to be less than lucrative.

After throwing his last pitch in 1983, Perry retired to his 500-acre farm in North Carolina as tobacco and peanut farmer. But business wasn’t good and within three years, Perry had filed for bankruptcy and had to recoup his debts the humble way — as a baseball coach for a local community college. He’s since bounced back, financially.

2. Johnny Evers

broke baseball playersThe man who revolutionized the double got hit with double financial trouble. Turn-of-the-century second baseman Johnny Evers’s name is known best for “Tinkers to Evers to Chance,” popularizing the shortstop-to-second base-to first base double play combo with teammates Joe Tinker and Frank Chance on the Chicago Cubs.

Evers went through two bouts of financial strain. Early on in 1910, he was the driver of a car accident that killed a friend, and suffering through a subsequent, deep depression, spent his life savings and went bankrupt after a pair of shoe store investments went under. Post-baseball, Evers opened a sporting goods store in Albany, N.Y. Bankruptcy didn’t elude him again, and in 1936, Evers filed for Chapter 11.

Photo credit: Out of the Park Baseball

1. Rollie Fingers

GoBankingRates listed famed relief pitcher and Hall of Famer Fingers as one of its five worst broke athletes ever, but he’s worth repeating again — not because of his strange facial hair choices, but his even stranger financial investments.

Fingers carved out the niche known as the late inning reliever, saving 341 games over a 17-year career with the Oakland Athletics, San Diego Padres and Milwaukee Brewers. Fingers’ relief pitching skills could have come in handy to salvage a losing game with several eccentric business choices.

The pitcher funneled millions of dollars into pet projects such as pistachio farms, wind turbines and Afghan race horses, but that only lasted three years. He eventually filed for bankruptcy, owing $4 million in losses. (At least he still has one pretty cool mustache going.)

Why Are There so Many Broke Baseball Players?

That’s the million-dollar question. Cliff Goldstein of the Wall Street Journal’s Market Watch wrote:

“Many athletes ‘go pro’ right out of high school or college, without ever having real world experience managing money or setting financial goals. Compounding this problem are financial ‘advisers’ who look to take advantage of athletes’ lack of financial knowledge and inability to keep track of their large bank accounts.”

Goldstein added that many athletes make unrealistic investments, combined with an overestimation of how long their careers will last.

Goldstein’s advice doesn’t just apply to professioanl athletes. Have clear financial goals, he wrote. “It’s easy to be outraged by athletes making large sums of money, spending it gaudily and then going bankrupt, but there’s an important lesson that can be learned from it: Long-term wealth outweighs short-term gains.”

Think of your finances as a baseball team — your dollars are your players, and you’re the manager. With some strategy and hard work, you can command a winning season that’s worthy of some true moneyball.

  • Tony Ciccolella

    As a baseball agent, I strongly encourage my clients to utilize financial advisors. Not just any financial advisor, but ones that are experienced in the lifestyle of the professional athlete and understands their Collective Bargaining Agreement and pension programs. Also, utilize tax professionals who also just specialize in professional athletes and communicate with the players financial advisors to help plan the players future. We obviously screen out the financial advisors and tax professionals first to ensure they meet our standards. Now obviously in the long run, it’s the players responsibility on how and what they spend money on but its good to know that our players have someone watching over their money and not investing in risky business.

    • LongTimeEconomist

      Tony, not all agents are as scrupulous or knowledgeable as you. As a one-time stock broker and a person who has acted as a money management advisor to some wealthy people, I have long thought that high income athletes should just be putting as much as they can into a no-load index fund like the Vanguard S&P index fund or a no-load balanced fund with a long history like Wellington Fund.

  • PatrickLA

    The one player who was a financial wizard at making money on sound investments was infact one its most despised, dirty players..Ty Cobb. He invested heavily in Coke when he had heard it was going to be put in cans and he made millions, which in the 50-60’s was a fortune!

    • Don Merkle

      Millions $$$ today..ain’t anything to sneeze at…PatrickLA…..Go Dodgers , exciting and fun team to watch…saw them take 3 of 4 in St. Louis last week. Am Missourian and strong WhiteSox fan. Lived in SoCal and Dodgers favorite NL team. donWsox

      • jg what PatrickLA wrote before your dumb comment…as he states, Ty Cobb made millions, which in the 50-60’s was a fortune…I swear to God people don’t read anymore, its either that or some people are just too damn dumb!

        • eagle2435

          jg, he is agreeing with him, saying having millions of dollars even today is good….its good to be able to read, but even better if you can comprehend what is written. You must be one of the ones who are just too damn dumb.

  • Don Merkle

    Reason Cardinals obtained “ROLLIE” and blew him” bye” before donning a Redbird Uni !..Ha I don’t know ! donWsox

  • jg

    Gwynn must have really sucked playing 29 years and only getting 3100 hits, how the hell does he bat over .300 then? Doesn’t anyone proof read things anymore….dumb ass!

    • GBR Casey

      via ESPN

      • DJ

        Gwynn only played 19 years, not 29. that’s why

  • Dick Delson

    They might be great ballplayers, but that doesn’t make them rocket scientists. The smart ones got financial advisers. The dummies are broke.

    • Colin

      It’s generally the ‘financial advisors’ who made them broke. Anyone can claim to be a financial advisor – there are no qualifications, just print up some business cards and off you go. Best advice for people like this (sudden wealth): Don’t go with one advisor – spread you money around between 3-5 of them, replace the one with the worst returns over a 2-3 year period, and never invest in a restaurant.