Category Archives: Tax Planning Strategies

Darryl Strawberry vs. the IRS: a 30-year battle goes on

Former baseball star Darryl Strawberry is learning that going to bat against the IRS is way tougher than hitting a major-league curve ball.

As Darren Rovell of ESPN reports, the Straw signed a contract with The New York Mets almost 30 years ago that included an annuity with a 5.1% annual rate. Now the IRS has seized the annuity, which currently has about $1.28 million remaining, and is going to auction it off toward paying more than a half-million bucks that Strawberry still owes the IRS for debts going back as far as the late 1980s.

The minimum bid for the annuity, which pays out through 2035, is $550,000. If you think the Mets will still be in business for the next 20 years and you’d like to bid on the annuity, you can find more information on the sale here.

“The Situation” is in a not-so-good tax situation

Did you know that “Jersey Shore” reality show personality Michael Sorrentino, aka “The Situation”, and his brother Marc, grossed almost $9 million in a variety of ventures over four years? Me neither, until I read the U.S. District Court indictment, reported inThe New York Times,charging the brothers with conspiracy and filing false tax returns. Michael…Continue Reading

How Oregon is helping a billionaire save some bacon on Bacon

There are two current mysteries about Francis Bacon’s Three Studies of Lucien Freud. First, who paid $142.4 million, the most ever paid for a work of art at auction, in November for the triptych? Second, why is it currently being displayed a mere three miles from my home, in the well-regarded-but-let’s-face-it-not-internationally-renowned Portland Art Museum? Can’t…Continue Reading

Apple avoids billions in taxes, and it all looks legal; those guys really are smart

Lawmakers are using words like “gimmicks” and “schemes” to describe how Apple Corporation has used a web of subsidiaries spanning the globe to avoid taxes. There are hearings this week at which Congressmen are expected to say they are shocked, shocked, to hear of tax loopholes being exploited. As The New York Times reported, Congressional…Continue Reading

Sex and the IRS: making “friends” with your IRS auditor, extreme version

Dear IRS: I’ve Read About This In Your Manuals, But I Never Thought It Would Happen To Me… Sometimes I sort through tedious tax court cases looking for some mildly interesting nugget to share, and sometimes a thing of sheer weirdness lands in my lap. An Oregon man has filed a lawsuit claiming that an…Continue Reading

Gay marriage at the Supreme Court: Taxes, as usual, are the key to everything

Edith Windsor saw the federal government claim more than $360,000 in taxes on the assets she inherited from her spouse’s estate when her spouse died in 2009. How could that be, when you are allowed to inherit an unlimited amount from a spouse free of estate tax? Edith’s spouse was a woman. She and Thea…Continue Reading

Morningstar says, “Go west — or east — for college savings plans.”

Morningstar, the mutual fund reviewer and financial advisory firm, has come out with its ratings of Section 529 college savings plans, with top ratings going to plans in Alaska, Utah, Nevada and Maryland. Morningstar’s top-rated plans: Alaska’s T. Rowe Price College Savings Plan (managed by T. Rowe Price Associates, Inc.), Maryland’s College Investment Plan (T.…Continue Reading

A potentially costly catch

Derek Jeter’s slog to 3,000 hits mercifully ends, and with a home run no less. A fan, Christian Lopez, is in the stands for his 23rd birthday and catches the ball. Fan agrees to give the ball back to Jeter. Yankee management buries fan in a pile of swag, including signed jerseys, bats, and premium…Continue Reading