The Tax Court(!) in the New York Times. Plus Art.

Earlier this week, the New York Times ran a fairly breathless story about Susan Crile, an acclaimed artist, and the Tax Court’s decision regarding her problems with the IRS. Ultimately, the Times says, this case is A. Big. Deal. The Times‘s lede:

If you say you are an artist, but you make little money from selling your art, can your work be considered a profession in the eyes of the Internal Revenue Service?

Spoiler: the answer is yes. Spoiler that the Times is apparently unaware of: we’ve known that the answer was yes for a long, long time. That is, although the Times assures us that the case is “seen by many as an important victory for artists,”[fn1] they’re wrong. This is, at best, a marginal victory (that will ultimately lead to a loss) for Ms. Crile. Continue reading

Ethics on Wall Street?

I recently started reading Confidence Games by Tanina Rostain and Milton C. Regan, Jr. The book is an overview and history of the late-90s early-2000s tax shelter explosion; I’m not far enough yet to have gotten to the details of the shelters (and the period slightly pre-dates the mid-2000s start of my legal career), but I just read a couple pages that made me reflect on my training in the tax department of Willkie Farr & Gallagher LLPContinue reading

Bruce Rauner and the Cayman Islands

On Friday, the Chicago Sun-Times ran an exposé on Illinois gubernatorial hopeful Bruce Rauner’s finances. Specifically, the Sun-Times informed its readership (and the world at large) that Rauner has at least a portion of his fortune in the Cayman Islands, a tax haven country.

To which I reply, Duh.

Seriously, I’m not entirely sure how this could be more of a non-story. But to explain why it’s a non-story, I should probably unpack what the Sun-Times says, what it doesn’t say, and what it probably should say.  Continue reading

The IRS Looked at Bitcoin . . .

bitcoinsA couple months ago, I posted about the problems with taxing bitcoins. In short, we didn’t know if bitcoins were currency or property. Largely, of course, the difference is immaterial: receipt of currency or property constitutes the receipt of taxable income, and using property or foreign currency to acquire goods or services constitutes a taxable realization event.[fn1] The most significant difference is that if bitcoins were property, any gain or loss could be capital, whereas if they were a currency, that gain or loss would essentially always be ordinary.

Continue reading