If you’re going to pull off a successful blackmail operation, you’ve gotta make sure the material you have is actually blackmail-able. Sure, you might have photos of your boss with another woman, but if he’s the head of your local Swingers Club, he’s both not going to care and might actually ask for additional copies.

One apparent blackmailer learned this the hard way after he confronted Madonna with photos he had of her as a 17-year-old showing a lot of skin. Apparently seeking some sort of attention or benefit from the singer, she instead responded that she a) didn’t care; and b) would recommend he save them until they become more valuable so he could sell them.

Power move.

When a man tried to sell to Madonna naked photos of her, thinking she will buy them so he won't share them in public, but she didn't give AF about it pic.twitter.com/1O32gTIhE8

— Madonna Daily  (@madonnaxdaily) August 19, 2025