Substance over Form: Friend of the Taxpayer?

Cases, Current Events, Income Tax, Tax Controversy, Tax Court

In the recent Complex Media[1] case, the Tax Court addressed a taxpayer’s ability to recast the form of a transaction under the “substance over form” doctrine. Since taxpayers typically control the form their transactions take, tax decisions routinely stick taxpayers with the consequences of that form. Some courts have precluded taxpayers from even raising substance…
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Is that Side Hustle a Business or Hobby?

Income Tax, Tax, Tax Controversy, Uncategorized

Hobby loss tax rules of IRC § 183 are nothing new. However, there are a couple of recent developments that make the application of those rules especially relevant: Starting in 2018, the Tax Cuts and Jobs Act (“TCJA”) went into effect. Under the TCJA, taxpayers lost the ability to take miscellaneous itemized deductions. Previously, taxpayers…
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Transfer to Third Party at Direction of Beneficiary Deemed Gift from Beneficiary

Estate and Gift Tax, Estate Planning, Tax, Tax Controversy

In a newly released Chief Counsel Advice opinion[1], the transfer of assets from a foreign entity referred to as the “Foundation” directly to a third party (the “Recipient”) at the request of the beneficiary of the Foundation (the “Beneficiary”) was deemed to be a gift from the Beneficiary to the Recipient. This is a logical…
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Ninth Circuit says Nice Try on Passive Rental Activities

Income Tax, Tax, Tax Controversy

Introduction The U.S. Court of Appeals for the Ninth Circuit recently affirmed a District Court’s ruling against a married couple who claimed their losses related to three vacation properties were not limited under the passive activity loss rules of IRC § 469.[1] The couple argued that the management company responsible for renting the property to…
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Lothringer and Alter Ego

Business Transactions, Income Tax, Tax, Tax Controversy

A recent case shows how a shareholder and corporation, being considered alter egos, can cause unintended consequences. In Lothringer,[1]a corporate shareholder’s individual property was subject to enforced collection action by the IRS to satisfy corporate tax liabilities.[2] The court’s finding that the corporation was the shareholder’s alter ego allowed the IRS to hold the shareholder…
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