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What do you mean he dressed shitty? Every photo I’ve seen of him he has a collared shirt and slacks on which is what people in Medellin wear if they’re older than like 55. I live in Medellin and see lots of older guys dressed like Pablo.
He just wasn't very fashionable. He dressed like a nerdy dad dropping his kid off at soccer practice. That stands out as an oddity to me for one of the most powerful men in the world.
Example:
I’m pretty sure that at the time that photo was taken he was in the middle of running for political office and hiding the fact his money came from drug trafficking. I assume that look you described was exactly what he was going for.
That makes sense. I was actually wondering if his goal was to appear less intimidating, and more average. I think it could also lead to his enemies underestimating him.