Category Archives: Tax Planning Strategies

Does Donald Trump pay no federal tax? Probably.

Why won’t Donald Trump release his tax returns? Maybe because he pays no federal income taxes.

David Cay Johnston, winner of the Pulitzer Prize, has come out with a new book, The Making of Donald Trump, and in an interview with Slate, he says that Trump, “probably hasn’t paid taxes in almost 40 years.”

That’s very possible (and legal), as The New York Times has pointed out in several stories, including this analysis from James B. Stewart.

Whatever he pays, Trump’s returns would in all likelihood be as fascinating as a return could be. Johnston has previously reported that Trump filed a return in 1984 with a Schedule C showing zero self-employment income and more than $600,000 in deductions.

You cannot make this stuff up.

“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