In the case of Commissioner of Internal Revenue v. Wemyss, the U.S. Supreme Court ruled that gifts made in contemplation of marriage are subject to federal gift tax under Section 1000(b) of the Internal Revenue Code. The respondents, Mr. Wemyss and Ms. Vandenburgh, had entered into an agreement where she would marry him in exchange for a payment from him worth $400,000 dollars; this was considered as part consideration for her promise to marry and part settlement upon her property rights after their marriage ended by death or divorce. When they filed their income taxes separately without including this amount as taxable gifts, it led to a dispute with the IRS which argued that these payments were not exempted from taxation because they weren't "made out of detached and disinterested generosity". The court agreed with IRS's argument stating that such transfers don’t fall within any statutory exception mentioned in Section 1000(b). Therefore, it concluded that Congress intended all transfers be taxed unless specifically excluded.

In the dissenting opinion for Commissioner of Internal Revenue v. Wemyss, Justice Robert H. Jackson disagreed with the majority's decision to treat property settlements in divorce cases as taxable income. He argued that such settlements should not be considered gifts under federal tax law because they are made out of legal obligation rather than generosity or affection. Furthermore, he contended that treating these transfers as taxable income would unfairly burden divorced individuals and could potentially discourage couples from seeking divorces due to financial concerns. His view was based on a belief that alimony payments were intended to provide support for an ex-spouse after separation, not serve as a source of revenue for the government.