Tax Tweaks For Your Consideration November 18, 2025November 17, 2025 In response to last Thursday’s post, How To Make $60 Billion, Bob F. reminded me that you’d have to win more than $200 million a week for more than 1,000 weeks in a row, not $100 million, because “the cash option is valued at less than half of the total of the annuity option.” And the other problem, Bob notes, is that “the jackpot resets to $50M after a win, so you can’t win $100 million (let alone $200 million) drawing after drawing. But luckily there are two drawings per week, Tuesday and Friday, so it will still only take 2000 weeks if you win every time.” Pull that off, in order to match the poorest of today’s 25 richest Americans, and you’d face yet another problem: In the 38 years of extraordinary good fortune it took to net $60 billion this way, the fortunes of those 25 richest Americans may have grown considerably. By just how much would depend, in part, on whether we reform the tax code. Which leads me to today’s topic. Tom L.: “A friend suggested that once you hit a net worth of $1 billion, you should be given a parade and a little award that says, “you won capitalism.” After that, all income is taxed at 100%. If you complain that you can’t live on $1 billion, we take the award away (at least you had the parade).” → I love it! Sort of. What I’d really like to see is an end to the “stepped-up basis at death” and other tax loopholes that make the estate tax a joke. And income from wealth and speculation taxed at the same rate as income from work (though I would keep the Qualified Small Business Stock exemption that incentivizes innovation). With that rate rising to 45% (say) on income above $25 million (say). And an IRS adequately funded to collect the taxes due — out of fairness to the majority who already pay every penny due. And a voluntary corporate tax surcharge — like this — that would only begin to kick in if the corporation’s highest paid employee (typically, the CEO) makes more than 50 times as much as her median employee . . . and that would steepen gradually to 5% when top total compensation exceeded a thousand times the median. Voluntary, because the board of directors could choose to raise median worker pay and/or limit top pay in order to avoid the tax if they felt that was in the best interest of the shareholders. If inequality has become a problem in America (and does anyone think it has not?), this would be a nice little way to lean against it. See, also, the Patriotic Millionaires Equal Tax Act. (To make tougher capital gains treatment more palatable, we should perhaps consider netting out inflation in calculating taxable gains. So if you had bought something for $1,000,000 40 years ago and sold it now for $2,500,000, you’d have no tax to pay, because after inflation you’d actually have lost money. As it stands now, you’d have to pay nearly $500,000 in federal and state tax on that capital “gain.” Now that virtually all preparation is computerized, the logistics of the calculations might not be difficult at all.) BONUS Who Will Replace MTG In Trump’s Clown Car— Andy Borowitz at his substantive best.