A recent opinion in the ongoing litigation in the case of Clair R. Couturier makes a really important point about the distinction between a penalty and a tax. We will get to that, but I would also like to discuss the larger story of the case as I struggle with what the lesson is. I thought this case might be a good illustration of Reilly’s Second Law of Tax Planning – Sometimes it’s better to just pay the taxes – but I’m not 100 percent sure, so I will let you be the judge.

Big Beautiful Promises of No Tax On This, That, and The Other Thing
President Trump’s campaign promises oriented toward working stiffs and geezers – No Tax on Tips, No Tax on Overtime, No Tax on Car Loan Interest, No Tax on Social Security – were not precisely fulfilled in the Big Beautiful Bill, but they were not ignored. Rather than the exclusion implied by “No Tax,” we get deductions. Just so we don’t miss the connection, the first three get their own chapter in the Big Beautiful Bill – Delivering on Presidential Priorities to Provide New Middle-Class Tax Relief. The bone thrown to seniors is an exemption.