March 25, 2025 at 2:21 am

He Won Big In A Raffle, But When They Tried To Guilt Trip Him Into Donating His Prize, He Stood Firm And Walked Away

by Benjamin Cottrell

man winning money in raffle

Canva/Reddit

Fundraisers often rely on generosity, but sometimes they end up running on guilt.

When a man won a 50/50 raffle, he was met with an unexpected request: Donate his winnings right back to a good cause!

Did not donating make him a Scrooge, or was he simply standing up for himself?

Read on for the full story.

AITA for not donating money I won in a raffle to charity?

Today, a buddy and I went to a local bar to have some lunch and a few drinks.

The place was pretty crowded.

On the other side of the bar, an organization was holding a fundraising event for a local animal shelter.

After about an hour, some people from the fundraiser approached us and were selling raffle tickets for their event.

There were a few different prizes, so the two ended up playing along.

There were two separate raffles.

One was for donated items such as a TV, camping equipment, etc.

The other was a 50/50 raffle.

Since I wasn’t interested in any of the prizes, I purchased $20 worth of tickets for the 50/50 raffle.

My friend did not grow up in the United States and was not familiar with the 50/50 raffle.

This type of raffle has a bit of a bad reputation.

I explained to him that the money raised was split 50% for the organization and 50% for the person who had the winning ticket.

I also mentioned that they often try to coerce the winner into donating the money back to the organization at the end.

About an hour later, someone from the organization got on stage and started announcing the winners of the raffles.

The last drawing was for the 50/50 raffle.

His assumptions about the raffle ended up coming true!

The emcee read the winning numbers, and I realized that I was the winner.

As I went up on stage to get my money, she informed me that it was $290.

As she handed me the money, she asked if I would be donating it to her organization.

My response was, “Did she ask the winner of the TV if he would be donating his winnings to the organization?”

Then, I shook her hand and walked off the stage.

AITA for not donating the money?

Knowing when to say know is probably one of the top five skills needed in adulthood.

What did Reddit think?

If it’s going to be a proper contest, then there has to be something in it for the winner!

Screenshot 2025 03 10 at 11.59.43 AM He Won Big In A Raffle, But When They Tried To Guilt Trip Him Into Donating His Prize, He Stood Firm And Walked Away

This user isn’t on board at all with the charity organizer’s unfair antics.

Screenshot 2025 03 10 at 12.00.37 PM He Won Big In A Raffle, But When They Tried To Guilt Trip Him Into Donating His Prize, He Stood Firm And Walked Away

There’s more than one way to be charitable.

Screenshot 2025 03 10 at 12.01.42 PM He Won Big In A Raffle, But When They Tried To Guilt Trip Him Into Donating His Prize, He Stood Firm And Walked Away

There’s nothing worse than a prize with a catch.

Screenshot 2025 03 10 at 12.02.17 PM He Won Big In A Raffle, But When They Tried To Guilt Trip Him Into Donating His Prize, He Stood Firm And Walked Away

Even in the face of pressure and societal expectations, this winner walked away with his fair share and felt good doing it!

Generosity should never feel like an obligation.

If you thought that was an interesting story, check this one out about a man who created a points system for his inheritance, and a family friend ends up getting almost all of it.