What's the best way to insult someone with a gift?

My personality disordered MIL is an artist at giving insulting gifts. An absolute master. She likes to pretend she is very poor, although isn't, and she volunteered at a Catholic charity shop for used goods, so she would take home armloads of used crap donated from the homes of deceased elderly people and would give them as gifts, none of which was any use to anyone and was quietly donated elsewhere afterwards. But she also likes to give you weird things that are basically trash, not because she can't afford gifts, but just to get negative attention and make people upset.

1. She gave me her old used bathrobe as a Christmas gift, which was pretty threadbare, and made sure to call me the next day to tell me it had been hers, which I had consigned to the garbage because it wasn't even really fit for donation.
2. She gave her only granddaughter an old vitamin bottle filled with dish soap and a discarded bubble wand she had found in the park. Not even one dollar for her grandchild would be spent, hell the dish soap probably cost more than buying a bubble blowing kit from the dollar store would.
3. She gave my BIL a sandwich baggie filled with used discarded golf tees that she had picked up walking the public course, all chipped and full of dirt. Another item easily found at the dollar store.
4. Years later her only grandchild had developed an eating disorder after being bitten on the face by a pit bull and needing several surgeries to repair as she was depressed about her appearance, poor kid. My MIL immediately went out and bought herself some size XXXXL pyjamas, and then dramatically announced to her grandchild's mother/her daughter that they were too big and she was going to give them to her grandchild, who is way thinner than her and would never fit them. We intervened and told her she was not to do that, and she immediately began squawking about what she could possibly do with them now. The whole point, if you don't speak personality disorder, was that she bought them simply to give them to her to send her a message that she was fat, even though she was absolutely not, and to also upset her daughter.

Top tier personality disorder behaviour really.

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.

Mouthwash, breath mints, deodorant.... Basically any hygiene product.

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

Most folks have at least 1 commonplace food item that they can't stand. This time of year food gift baskets are everywhere and often specialized to certain tastes. So you get them something that looks like a nice goodie basket but then most things in it are tainted by a thing they don't like.

For me it would be licorice / anise.

Make a charitable donation in their name, and put it in a card. This is actually genuine as you spent actual money, but it’s also kind of an anti-gift. Sometimes the donation even gives you a free gift like a calendar or T shirt which you can pass along. Some people may be triggered by specific charities like The Satanic Temple, or Planned Parenthood. I would be quite upset if somebody gifted me a PeTa donation. But in that unlikely event, I would laugh and gift them back a Heifer International donation.

Get them soap and instructions about maintaining proper hygiene.

I think something that goes against their personality. Someone who hates the spotlight give an improv class, someone who's afraid of heights a rock climbing class, for picky eaters a food tasting, I hate listening to instructions so I hate yoga so if you got me a yoga class. Even better if you go with them so they can't back out. It's easy to say I wanted to get you out of your shell and thought you would like it if you tried it.

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.

Give them a gift card, but you've spent more than half of it.

Or give them a gift card to a store that either does not exist in their area or a store that they wouldn't want to shop in.

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.

One trick I heard is to get them a gift card towards a Las Vegas vacation. If they go to Vegas they are way more likely to lose money than win at the tables.

Season tickets to Manchester United.

The best way is the one where you know lots of (not so well-known) context and circumstances, and then it can work as an insult, but you can deny some of the knowledge and therefore you can appear innocent.

Save your money

"Oops I forgot" is a powerful weapon here: condoms for a buddy who's trying for a baby, funny dog meme for a person whose dog just died, gift certificate to romantic restaurant for someone who just broke up with their partner, etc. They can't prove you didn't forget about their issue

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 gift card for a shop that sells cringe stuff only

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.

Premium expensive aftershave be sure to get it giftwrapped aswell. It can be a knockback whammy, you tell them they stink and you pay an arm and a leg to tell them.

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

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.

Birthdays: birthday cake flavored vodka (implies they are a drunk)

You could get them a bag of dicks

if they think they are funny then get them a rubber chicken. if they are stinky get them perfume.

A large bottle of cologne. Plausible gift that makes them think they smell bad.

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

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

xs condom and a blow-up doll

A fruit bouquet

To take the higher ground with kindness and empathy

Gift them a panda.

Christmas fruitcake.

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.

Give them something you know that they hate

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