I feel as though if you know someone is into something like Lego or something similar, getting them something completely offbrand from somewhere online, not opening the box it was shipped in, and then explaining the post said it was official and that you can’t return it because you ordered it a couple months back could work.

That, or if you are in scouts, you could try and pull what our troop did once for a white elephant gift exchange during one winter court of honor and get rid of an old tent. Our troop got new ones not that long before the event and an old tent was then added as a white elephant gift, probably from our scoutmaster at the time. I ended up trading with one of my friends for that tent rather than the dumb looking card game I had been saddled with. Either way, getting rid of an old tent this way feels a bit insulting to whoever gets it, to me at least.

If they’re in the hospital, a potted plant.

Find out something that they were passionate about in life, but left by the wayside because they were ultimately a failure in it. Then get them something related to that. But make sure the gift is flawed in some way to be totally unuseable.

A gym membership. Implies overweight.

Makeover service. Implies not looking so good.

If you know a right-wing prepper, get them a subscription to Mother Earth News, a magazine that touts self-sufficiency and off-grid living with occasional ads that lean to conspiracy theories like “free energy”. It’s full of food saving and growing ideas. It’s also liberal AF.

Charitable donation in their name to an organization they likely oppose, but not “in your face”. Like if they’re republican, don’t donate to a blatantly liberal org, donate to one that teaches kids critical thinking skills and welcomes lgbtq or something like that. They get the tax writeoff, a real benefit, but would have to be visibly hateful of they rejected where the money went. Edit: how about a LGBTQ shooting camp. That’d take some mental gymnastics.

Gift tickets to a nice cultural event to someone that is anti-lgbtq. Local city playhouse has an Opera with lots of men in tights.

Any subscription or service that makes potential commentary on personal appearance or personal beliefs would be effective.

At one workplace secret Santa (which I always declined to participate in), one recipient got an empty spherical clamshell with cardboard retainer on which was printed the word “Nothing”, visible through the clamshell. The joke being that it was supposed to be “I didn’t know what to get you, so I got you nothing.”

This was not intended as an insult by the secret Santa, but was taken as one by the recipient who must have spent significantly more on whatever their recipient got.

Only you can judge how your recipient would take such a gift, but if this seems like a good idea to you you can probably find them on sale somewhere. (NB: I accept no responsibility if you choose this course of action.)

If I remember correctly, one of the recipients of a better gift thought it was funny so swapped their gift with it to cheer up the unhappy recipient. I am not sure if the swapper was their secret Santa or not.

There had been much offence, pouting and sulking… from a grown man.

You could get them a bag of dicks

paper bag full of dog dookie, with “plant fertilizer” written on it

Something utterly meaningless, like a bag of generic candy, from the closest corner store “wrapped” only in that store’s type of plastic bags, clearly purchased last-minute on your way over to them. As they unwrap it you slip an “oh, I forgot to take that” and snatch up the receipt that you’ve forgotten in the bag, but only after they’ve seen that the item was on sale for $0.99.

Any gift that suggests they need to improve something about themselves, especially if they’ve never shown any interest in that. Like a gift card for skincare treatments, or teeth whitening. Maybe a self-help book, or some exercise equipment. Cologne/perfume is good for deniability, but it might come off as more romantic than intended.

Also, giving any of these gifts to make someone feel bad about themselves makes you an enormous asshole. Use your words, be honest with people, and don’t go out of your way to humiliate or irritate people you don’t like. Life’s too short to spend it scheming.

Someone called it insulting once when I donated all my socks that didn’t have a second sock.

I liked the Canadian government giving Trump a framed photo of a former family business established in the Yukon: a bordello!

To take the higher ground with kindness and empathy

The cheap brand of something they know is crap. Say they are into water colour painting, get them the cheapest set you can find on Amazon, but not so cheap that it looks like a kids gift.

That really depends on the person and what they perceive as an insult.