So like, according to the organizers, if they were born with a penis, it doesn't matter if they transitioned, they are considered men.

This trans man (a person born with a vagina who transitioned ) is entering the contest, because if trans women are considered men, trans men are considered women.

So this dude is entering a "female" beauty contest to show how dumb the rules are. He is allowed to do so because said dumb rules make him a woman in the eyes of the organization.