Treasury Secured Puts (TSPs)

Frankly, I think this is confusingly formuated by Thierry De Mitri … maybe on purpose as their business is tax advising? Honi soit qui mal y pense …

These are the relevant passages from your quote above:

What Uncle Sam will pay me at the May 31 2025 maturity of my treasury note is the principal aka nominal aka par value of the bond plus the final interest due on May 31 2025.
I’ll pay income tax on that final interest payout of 0.25% but certainly not on the nominal.

That third quoted sentence above is particularly confusing, as it kind of implies that “the reimbursement” is the debtor paying back the principal at maturity and that this is taxable, while in fact it’s only any reimbursement above the principal that would be taxable, i.e. the final interest payment.

Anything else wouldn’t really make any sense, would it? Think about it: you lend someone money (let’s say no interest, it’s your friend). They pay back that money to you. That’s not income, is it?

No, doesn’t worry me. I carry only few Put positions over the year end to avoid suspicion and it works out fine. See this post for a more detailed discussion.