Continuing our series on Famous Tax Quotes (quotes from court opinions and rulings with language that is colorful or that concisely states an important tax principle), in Caylor Land Development, Inc. v. Commr., T.C. Memo 2021-30, the Tax Court analyzed whether an Anguilla insurance company was providing “insurance.” It first held that there was no risk distribution, and therefore the company was not providing insurance. The Court also held, as an alternative ground, that what the company was selling was not “an arrangement that looks like commonly accepted notions of insurance.” In discussing this alternative ground, the Court stated:
Writing and delivering “claims made” insurance policies after the claim period is * * * just plain silly. * * *
The calculations of the premiums * * * started in a normal place * * * [b]ut the calculations soon took a detour to crazy town.