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.

The One Big Beautiful Bill Act relieves some of the tax burden that comes along with tip income for tax years 2025-2028. But not in some of the ways that it was initially explained. Yes, tip income is still taxable income. No, customers do not have to pay tips in cash for them to be deductible. But the tip does have to be voluntary, qualified, and reported to the IRS.

Do you love giving your clients great news? I do. Especially when it is about a tax benefit they can receive as the result of the hard work that they have put in throughout the tax year. That is what the overtime deduction is for the taxpayer. A little bit of tax relief for their hard work. But before sharing the good news with them, we need to make sure that we understand that No tax on overtime is not a blanket statement that will apply to all overtime compensation and all taxpayers. It is our responsibility to do our due diligence to understand who it will impact and how.

The tax code is not kind to gamblers. All gambling wins are reportable as income. Losses are only deductible to the extent of wins and even that has limitations. Expenses of gambling, such as travel, meals, and lodging, are not deductible for casual gamblers. In Part 1of this two-part article we will discuss deducting gambling losses for recreational and professional gamblers. We will also discuss additional deductions professional gamblers can take and how they were affected by the OBBBA.

This month's Tax Court cases feature warnings to lawyers (and appraisers?) in the ongoing syndicated conservation easement wars; teasers about the impact of Loper Bright Ent. and Section 7701(o)(1); useful practice tips, and the conclusion of Boechler, P.C. (equitable tolling won't save a losing case).