On March 10, 2021, the Tax Court issued a Memorandum Opinion in the case of Caylor Land & Development v. Commissioner (T.C. Memo. 2021-30). The primary issues presented in Caylor Land & Development v. Commissioner were whether consulting payments made between the petitioner and its microcaptive insurance company were ordinary and necessary business expenses or insurance expenses. Brief Background (to Lay a Foundation for Judge Holmes’ Puns) in Caylor Land & Development v. Commissioner The