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T-bills are highly liquid.
Better yet, if he kept it in the SP500 then it would be liquid and a better investment than whatever Trump Org is doing.
Depending on what maturity rate you choose. I think the shortest is little over a month?
Not super liquid if you are considering taxes.
Liquid means something can be sold quickly for its market value. In other words there are lots and lots of potential buyers bidding for it, so low-balling won't work, so you will get a fair price. Whereas an illiquid investment, like real estate, has few potential buyers. If you are in a hurry to sell real estate, buyers can lowball you.
Liquidity has nothing to do with whether it is wise to sell right now.
T-bills are constantly bought and sold on the secondary market before maturity, the maturity value is built into the market price. If your T-bill matured in 10 years you could sell it tomorrow if you wanted, and you would get a fair price.
You can find quotes here. Want a T-bill that matures on Mar 31? You can easily buy it. Or sell it.
Taxes depend on if your investment was profitable, not liquidity. Something can be illiquid but subject to no taxes (if you lost money on it) or very liquid but subject to high taxes (if you made a lot of money).
Of course, it's possible that selling an investment today wouldn't synergize with your particular tax avoidance strategy. But that's not a liquidity problem, that's a you problem.
You're right, that guy doesn't know much about liquidity. Trump could have parked his money in T-Bills and made 4.8% annually on them, risk free. And no state taxes.
Sounds like a smart thing to do if you're going to pay a fat judgement. Trump is bad at planning and shouldn't get the benefit of the doubt. He just didn't plan on losing at all.