Jake knows Olivia is hiding Russell across the hall. He tries to tell her that Russell will never talk no matter how much they torture him. The guy is just like him. The only difference is that Jake is in love with her. Command would call that a defect. This is something Russell doesn't have. Their conversation leads to Olivia recalling some not-so-fond memories. Watch this scene from Scandal Season 4, Episode 21: A Few Good Women.