Audrey Walton put $200 million of Walmart stock into two GRATs and reported a $0 taxable gift. The Tax Court blessed it, and casino magnate Sheldon Adelson later moved $7.9 billion to his heirs the same way. Here is how the grantor retained annuity trust estate tax strategy works, the Walton case that made it bulletproof, and what a zeroed-out GRAT saves at the 2026 numbers.
Donald Trump claimed a $21.1 million charitable deduction for a conservation easement on land he kept. The strategy is legal, but the fight is always about the appraised number. Here is how the conservation easement tax deduction works, what the §170(h)(7) crackdown changed, and how the 2026 charitable rules shift the math.
Peter Thiel turned a $1,700 Roth IRA into a $5 billion tax-free account by buying founder shares inside it. The strategy is legal, but the line between a brilliant move and a detonated IRA runs straight through IRC §4975. Here is how it works and where it goes wrong.
Your RSUs vested, the company sold shares to cover the tax, and you still got a five-figure bill in April. The reason is the flat 22% supplemental wage withholding rate. If your bracket is 32% or 35%, that rate is built to come up short. Here is the 2026 math and the two ways to close the gap before you owe a penalty.
High earners are told the backdoor Roth is a free move: contribute to a nondeductible IRA, convert it, owe nothing. Then the tax software says most of the conversion is taxable. The reason is the pro-rata rule and the old rollover IRA you forgot about. Here is the 2026 Form 8606 math and the one fix that has to happen before December 31.
Most people think the inherited IRA 10-year rule just means emptying the account by year ten. After the IRS final regulations, a non-spouse beneficiary of someone who died after their required beginning date must take an annual RMD in years one through nine, and the real cost is the tax bill waiting in year ten. Here is the 2026 math.
Company stock sitting in a 401(k) can be distributed in kind so the appreciation is taxed at long-term capital gains rates instead of ordinary income, while a full IRA rollover taxes every dollar as income later. The net unrealized appreciation election under IRC §402(e)(4) turns on one lump-sum distribution and one triggering event. Here is the 2026 math.
A gain rolled into a qualified opportunity fund today defers only to December 31, 2026, with no basis step-up, so the deferral is gone almost as soon as you claim it. Wait until 2027 and OBBBA's OZ 2.0 gives a rolling five-year deferral plus a 10% step-up, 30% in a rural fund. The 180-day rules are what let a 2026 gain make the trip. Here is the math.
OBBBA made the excess business loss limitation permanent and reset its threshold, so for 2026 a noncorporate taxpayer can deduct only $512,000 of net business loss on a joint return against nonbusiness income, down from $626,000 in 2025. Everything past the cap becomes an NOL carryforward usable against no more than 80% of future income. Here is the §461(l) math and why it bites the cost-segregation and short-term-rental crowd hardest.
A rental with an average guest stay of seven days or less is not a 'rental activity' under §469, so its losses are not automatically passive. Materially participate, and a cost segregation study can drop a six-figure loss straight onto your W-2 income, no 750-hour real estate professional test required. Here is the 2026 math and the three places it quietly fails.
A vehicle rated over 6,000 pounds escapes the $20,300 luxury-auto cap that cripples ordinary cars. But the Section 179 deduction for it stops at $32,000 in 2026, and the tool that actually writes off the full SUV is 100% bonus depreciation, which the One Big Beautiful Bill Act just made permanent. Here is the 2026 math and the door-jamb label that decides it.
OBBBA raised the SALT deduction cap to $40,000, then phases it down to $10,000 for incomes over $500,000. For a business owner who pays more than that in state tax, the pass-through entity tax election still deducts every dollar at the entity level, above the cap and outside the phaseout. Here is the 2026 math.
