Juan Manuel Sánchez Gordillo, Mayor of Marinaleda from 1979 to 2023 (among other things) has been described exactly as a “modern Robin Hood” in newspapers^[1], especially in reference to their supermarket raids:

https://en.wikipedia.org/wiki/Juan_Manuel_Sánchez_Gordillo

In mid August 2012, Sánchez Gordillo attracted considerable media attention both within Spain and internationally due to his role in raids on supermarkets in nearby towns, Seville and Cádiz, where food was stolen and handed out to poor families and to food banks. The items stolen were part of a list chiefly made of rice, sugar, pasta, milk, olive oil and flour. Sánchez Gordillo did not personally remove food, but was outside in the car parks while members of his union conducted the raids. Several of these members have been arrested and later released, though Sánchez Gordillo himself has immunity from prosecution. Sánchez Gordillo has however said he is happy to waive his immunity and go to jail for his cause, in fact he said he expected to be jailed in order to make his message spread further.

I could make an argument that Director of Development positions at community charities would fit a Robin Hood role. They aren’t fundraisers, they are tasked with schmoozing and convincing rich folk to hand over large sums “to leave a legacy”. And then the charity turns around and helps whatever group of less fortunate they feel mission-driven to help.

Begging doesn’t really work for the big dollars. You have to use psychology, and that can be twisted to appear as manipulating/robbing the rich.

Billionaires rarely walk around with pouches of gold anymore, and probably most have some sort of personal security as protection against kidnapping and ransom. Security who, if we’re honest, are probably better trained, equipped, and fit than would-be Robin Hoods.

Not saying it’d be impossible, but the Hoods would have to do the kidnap thing and that rarely works.

Man I wish, my pathetic bank account needs some serious help… just like millions of others I’m sure.

<unpopularopinion>Bill Gates?</unpopularopinion>