Not an exact match to your wording, but the first thing that comes to mind is

Costanza

For white Americans of a certain age, the most powerful example of the kind of wrongness being described is an episode of Seinfeld where the character George Costanza realizes that every single decision of his life has been the wrong one. He reverses course and consciously opts for the exact opposite of any decision he needs to make. By the end of the episode, he has a lovely girlfriend, a new home, a better relationship with his parents, and a job working for the New York Yankees by insulting their owner George Steinbrenner to his face.

As far as phrasing, you'd just work his name into a simile or metaphor or one of the informal expressions like pull a..., did a...

Not an exact match to your wording, but the first thing that comes to mind is

Costanza

For white Americans of a certain age, the most powerful example of the kind of wrongness being described is an episode of Seinfeld where the character George Costanza realizes that every single decision of his life has been the wrong one. He reverses course and consciously opts for the exact opposite of any decision he needs to make. By the end of the episode, he has a lovely girlfriend, a new home, a better relationship with his parents, and a job working for the New York Yankees by insulting their owner George Steinbrenner to his face.

https://www.youtube.com/watch?v=cKUvKE3bQlY

As far as phrasing, you'd just work his name into a simile or metaphor or one of the informal expressions like pull a..., did a...