By Allan Sloan

This is commentary by Allan Sloan, an independent business journalist and seven-time winner of the Loeb Award, business journalism's highest honor.

I've never gotten along with President Donald Trump. I wrote articles criticizing his business practices and overpriced casino purchases in the 1980s and 1990s; we had a nasty final argument about 30 years ago that he started by calling me and that I ended when I slammed down the phone on him with a curse; and I've never gotten anything resembling a civil response from him or his representatives since he entered the national political scene a decade ago.

But despite the wretched history between us, I'd really like him to appoint me to a high-level post, something that would make him my boss.

Why do I say that, albeit with my tongue tucked firmly into my cheek? Because that would allow me to benefit from a little-known tax break that Trump's billionaire and centi-millionaire appointees are benefiting from.

And that megawealthy appointees of Democratic presidents have benefited from, as well.

Here's the deal.

If you're appointed by the president to a job that is subject to conflict-of-interest rules, you don't have to pay federal capital-gains tax when you sell the assets that pose the conflict, provided that within 60 days of the sale you invest the proceeds in U.S. government securities or a diversified equity investment such as an index fund.

No, I'm not making this up. This break is embedded in Section 1043 of the Internal Revenue Code, which tax expert Robert Willens hunted up for me at my request.

This provision, passed in 1989 when then-President George H.W. Bush wanted it to be easier for wealthy Wall Street types to join his cabinet, is designed to keep public service from being prohibitively costly for people who have assets on which they have substantial gains.

To be sure -- three of my favorite weasel words -- unlike some parts of the tax code, Section 1043 isn't a total loophole. Why not? Because if you sell the assets that you bought with the tax-deferred money from selling the assets that posed the conflict, your tax basis -- the assets' cost for tax purposes -- reverts to what you originally paid for those conflict-causing assets.

Willens says, however, that there's a solution to that problem if you've got patience and enough other assets and income to pay your bills. To wit: if you hold on to the assets you bought with the conflict-sale proceeds until you die, your heirs get to step up the basis, tax-free, to what the assets were worth on the day that you passed away.

Pretty neat.

To be sure, no one is going to confuse my financial statement with those of billionaires such as Treasury Secretary Scott Bessent, Commerce Secretary Howard Lutnick, or Education Secretary Linda McMahon.

But my wife and I are long-term investors who don't do much trading, and we've got stocks (which I won't disclose, unless the Senate takes up my nomination) that we've held for years on which we have substantial gains.

So I'd love to be able to sell them and diversify our assets without having to pay Uncle Sam a share of the proceeds.

It turns out that there's no regulation about how long you've got to stay in the job to keep the federal tax deferral. So in theory, I could sell the conflict assets, stay in the job that Trump gave me for a few weeks, then resign and resume my regular life. That would be lucrative but incredibly tacky.

As I said, I'm writing this article tongue in cheek. I'm not holding my breath waiting for a presidential appointment and I wouldn't be foolish or arrogant enough to accept one in the unlikely event that Trump offered to nominate me for it.

But as April 15 approaches, it sure is fun to contemplate the tax break that I'd get from a presidential appointment. Even though I know I'll never get it.

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March 11, 2025 01:30 ET (05:30 GMT)

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