Summary

Thurgood Marshall Woodward v. Commissioner of Internal Revenue…

That uncertain and difficult test may be the best that can be devised to determine the tax treatment of costs incurred in litigation that may affect a taxpayer's title to property more or less indirectly, and that thus calls for a judgment whether the taxpayer can fairly be said to be 'defending or perfecting title.' Such uncertainty is not called for in applying the regulation that makes the 'cost of acquisition' of a capital asset a capital expense.
Source: Wikisource

Thurgood Marshall Woodward v. Commissioner of Internal Revenue…

More fundamentally, however, wherever a capital asset is transferred to a new owner in exchange for value either agreed upon or determined by law to be a fair quid pro quo, the payment itself is a capital expenditure, and there is no reason why the costs of determining the amount of that payment should be considered capital in the case of the negotiated price and yet considered deductible in the case of the price fixed by law.
Source: Wikisource

Thurgood Marshall Woodward v. Commissioner of Internal Revenue…

In our view application of the latter regulation to litigation expenses involves the simpler inquiry whether the origin of the claim litigated is in the process of acquisition itself.
A test based upon the taxpayer's 'purpose' in undertaking or defending a particular piece of litigation would encourage resort to formalisms and artificial distinctions. For instance, in this case there can be no doubt that legal, accounting, and appraisal costs incurred by taxpayers in negotiating a purchase of the minority stock would have been capital expenditures.
Source: Wikisource

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