Put options cap your downside, and cap your time horizon. You can pay the premium for a very long horizon if you want -- if you think the company is going to fail all the way to zero, the prices pretty far out of the money are often pretty low even at 2 years out.

It would be pretty disappointing if the stock kept climbing and then crashed 2 days after the options expired; but at that point you might have given up on your traditional shorts as well.

It would be even more disappointing if the stock barely moved, and then crashed 2 days after the option expired. In that event, the put goes to zero and the traditional short wins the jackpot.

A more abstract way to make the same point is that a put or call is making a bet about volatility, whereas traditional long or shorting is a pure directional bet.

I know this pain. I bought some Jan 19' $10 put options in Kodak right after they announced their nonsense cryto abomination.

I knew it had run on speculation and was going to come down. The problem was I timed it wrong. By Feb 7th after my options expired Kodk was trading in the mid $2 range, down from $11. I lost my entire option bet, oh well. Lession learned.

I think frequently about buying puts but never pulled the trigger. It's so, so tempting because in cases like that, you are 100% sure that you're right, and in fact you actually are right.

The last time I thought of buying puts was a month ago when Tesla was at 350$, propped up by the "funding secured" claim. It was so obviously bogus and a sign of desperation. But I was terrified of buying an all-or-nothing lottery ticket, so I didn't. That one would've been a big winner and now I feel the pain of missing out. Hearing your similar Kodak story is useful to reinforce my resolve that I should just stay with vanilla investing strategies.

The traditional short has to close their position at some point is well. It’s never an unlimited duration.