Baseball’s Biggest Tax Cheats
Posted by: Richie Rich in Autographs, Baseball Cards, Baseball Law, Pete Rose, Taxes
Baseball has a long history of its players cheating.
Spitballs, corked bats, interference, sharpened spikes, stealing signs, and performance enhancing drugs among those transgressions.
And sometimes, there’s cheating that happens off the field. And not just marital infidelity. There’s also the guys who try to cheat Uncle Sam out of his take.
So in honor of this April 15th – TAX DAY – here’s a look at Baseball’s biggest tax cheats. Well, the ones who got caught anyway.
Derek Jeter
In 2001, Jeter purchased a $13 Million Apartment in Trump Towers near the World Trade Center. Which would make you think he’s a resident of New York. But Jeter has claimed to be a resident of Florida since 1994 … I wonder if it’s merely a coincidence that Florida has no state income tax.
Well, the New York Department of Taxation and Finance didn’t think it was a coincidence, and in 2007 charged Jeter with evading three years worth of Taxes from 2001-2004. New york said that Jeter was indeed a resident of the Empire State and not the Sunshine State.
Jeter reportedly settled the case with New York in 2008. The terms and value of the settlement are unknown.
Barry Bonds
Okay this one is totally speculative and unofficial since the Feds didn’t include any Tax Evasion charges in their indictment of Bonds back in 2007.
But it was widely reported in 2006 that Bonds handed over at least $80,000 in ”possibly undeclared $80,000 in cash from memorabilia sales” to his mistress, Kimberly Bell. Bell said that Bonds “instructed her to deposit the money in amounts less than $10,000.”
My guess is that the Feds dropped the Tax Evasion charges because Bell was an unreliable witness – she’s got man-hands, after all.
Willie McCovey
In 1986, McCovey was inducted into the Baseball hall of Fame, presenting him with even more lucrative cash opportunities to appear at card and memorabilia shows.
However, from 1988-1990, McCovey underreported his income from those shows by $69,800 and as a result, received two years’ probation and had to pay a $5,000 fine in 1995 for tax evasion.
McCovey claimed a hired accountant made the error.
Duke Snider
Also in 1995, another Hall of Famer fell victim to tax evasion charges. Duke Snider, the former Brooklyn/ Los Angeles Dodger great was nailed with two years’ probation and $5,000 fine after he pleaded guilty to failing to report $100,000 in income from promotional appearances at card and memorabilia shows from 1984-1993.
Snider apologized and acknowledged his wrongdoing
I made the wrong choice. I was knowledgeable. I was aware of the crime I was involved in. And I made the wrong choice. I hope the effects of it won’t hurt baseball that badly
Both McCovey and Snider were nabbed in part to a 1989 Card Show in Atlantic City that showcased the 11 living players who had hit 500 Home Runs.
Darryl Strawberry
In 1994, the IRS slapped Strawberry with a lien after he underreported his income by $502,043 from 1986-90. Once again, it was income from card and memorabilia shows.
The following year, Straw cut a deal and pled guilty to one count of tax evasion - he had to spend six months in home confinement and then 100 hours of community service. The deal allowed him to keep playing baseball.
In 2008, Strawberry started paying some of it back, agreed to pay back the IRS for 1989 and 1990 back taxes.
Cecil Fielder
In late 2008, the IRS filed a lien against Fielder for $273,123 in unpaid taxes from 2001-2004.
It’s just one of many examples of the poor monetary choices the former slugger has made in his career, mostly stemming as a result of his massive gambling debts. It’s also belived to be one of the reasons he and his son are no longer on speaking terms.
Speaking of his son …
Prince Fielder
As much as the younger Fielder would have you believe he’s unlike his old man, the IRS thought differently in 2005 when it slapped Prince with a Lien for $409,149 in unpaid taxes.
The taxes were from 2003, when Fielder received his $2.4 million signing bonus from the Milwaukee Brewers. To his credit, Fielder paid off the lien in January 2009, before he signed a new two-year contract with the Brewers.
Pete Rose
In 1990, Rose pled guilty to two charges of tax evasion. Rose admitted to filing income tax returns that did not show income ($345,967) from selling autographs, memorabilia, and gambling winnings.
Rose was fined $50,000 and sentenced to five months in prison and 1,000 hours of community service. He also had to pay the IRS over $350,000 in back taxes and interest. Rose was released from prison in January 1991.
And if that wasn’t bad enough … Rose got slapped AGAIN in 2004 when the IRS filed a Lien for $973,693 in uupaid taxes from 1997-2002. This time however, Rose acknolwedged the debt and tried to negotiate payment terms.
Wesley Snipes – Okay not a ballplayer, but he played a convincing one in “The Fan”



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April 16th, 2009 at 11:02 pm
I always love when they say Rose cheated paying taxes on gambling winnings. Last I looked it was illegal to bet in Ohio on that stuff. How can you tax illegal income?
And what about the dude? (Lenny Dykstra) aside from business people saying he owes them a fortune. I thought he had some tax issues a few years ago as well.
April 17th, 2009 at 8:53 am
Spike -
To the IRS, all income is income.
Even if it’s illegal income. You are supposed to report gambling winnings as income.
You can also deduct gambling losses … but only to the extent of your gambling winnings.
Richie Rich, CPA
not kidding
April 18th, 2009 at 7:54 am
Hmm I’d like to see a “Pimp’s” IRS return. (Insert tasteless joke here.)
No wonder this blog lakes updates since Richie is a CPA!
Glad your not still upset over that link, you thought I was Spaming.