He set up the security guard, Chuck Eastman, to get locked up. Everyone at the prison already didn't know who Simon was supposed to be. What does Simon think would happen when he goes missing after a prisoner is broken out, and Chuck is left in a maximum security prison for superheroes and villains
The security guard just got a life changing amount of money deposited into his account. Does Simon think the government won't take the money and lock him up
The way this ended shows that his brother was right, and he's a selfish person that only thinks about himself. He could have came through the next day, and broke Trevor wearing a Doorman mask.
I don't think it was a failure of Simon's character, but a failure in the writing for the show.
