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Charlie Sheen’s Income Tax Woes – Things Are Looking Better
When it comes to celebrity gossip, Charlie Sheen, who I mainly remember as the star of Two and A Half Men, is in a class by himself. You could, for example, look up the Charlie Sheen Effect, if that sort of thing interests you. At any rate, given all his other issues, it is not shocking that he has tax troubles. The IRS has been trying to collect from him for the years 2015, 2017 and 2018. He recently got some good news from the Tax Court and there may be some lessons worth learning from his case. Based on the public record, we don’t know how much the IRS is trying to get from Charlie Sheen. It is reasonable to infer that it is considerably more than the $3.1 million offer in compromise that the CPA and United States Tax Court Practitioner Steven Jager negotiated for Sheen. We also don’t know whether any of what the IRS is looking for is the result of an audit or whether it is entirely the result of Mr. Sheen filing without paying. Continue reading to learn how to negotiate your tax debt like a celebrity.
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Lessons Learned from the Tax Court: The Root of the Issue
When is a business really a business? As Supreme Court Justice Potter Stewart said in 1964, “I know it when I see it.” The US Tax Court, however, maintains a slightly less subjective standard. The Roots were pretty sure they were running a bona fide business; the IRS, however, didn’t share the sentiment. And since we’re reading about them in a segment called “Lessons Learned,” one should assume it did not go the way the Roots would have liked.

The Lessons From The Supreme Court Zuch Opinion
There is a great scene in the movie On The Basis Of Sex. The actors portraying Ruth Bader Ginsburg and her husband, Martin Ginsberg, a very high-level tax attorney, early in their careers are reading in separate rooms. He comes in with something he wants her to read and she snaps that she doesn’t read Tax Court cases. In that moment she showed her future as a Supreme Court Justice. Not many Tax Court cases reach the Supreme Court. So when one does it’s exciting. And, as it happens, Commissioner of Internal Revenue v Zuch contains some practical lessons worth considering.

Fractional Art Investing Is Real — How To Advise Your Clients On The Tax Consequences
In mid-November a portrait of a young Vietnamese woman by the artist Gustav Klimt, which was part of the estate of the late Leonard Lauder (the cosmetics billionaire), was sold at a Sotheby’s auction for $236.4 million. It set the record for the most expensive work of modern art ever sold at auction according to Bloomberg. That’s probably out of reach for most of our clients. But what if they could join together to buy an interest in the painting with an entity holding the asset? That’s the idea behind the burgeoning fractional art market. While, in general, the art market has been struggling for a few years, the fractional art market has been expanding. According to the website Digital Original, “Fractional art ownership is no longer a niche concept – it’s a growing investment trend that’s accessible, flexible, and supported by cutting-edge technology.” What, you may be asking, does this have to do with taxes? It may be more than you think for your high-net-worth clients. As a trusted advisor it’s important that you are aware of both the types of investment opportunities your clients may be buying into and the tax consequences.
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