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.

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Tax Evasion and Swedish Supergroups

ABBA-early-costumesLike any American who has ever been to a dance or listened to the radio, I’ve heard ABBA’s “Dancing Queen.”[fn1] But in the last week or so, I’ve learned a couple new things about them. A week ago, listening to Sound Opinions’s Valentine’s Day episode, I learned that the band was made up of two married couples.[fn2] And yesterday, thanks to several friends on Facebook, I learned that (a) ABBA used to dress outrageously, and (b) it was apparently for tax reasons. Continue reading