Headlines we’re sure to see It’s not as if the question of Donald Trump running for president from jail hasn’t been addressed before. It’s just that Trump’s arrest seems more imminent. The chances of Trump actually being held in jail pending trial for any of four separate investigations seems remote. That doesn’t stop the speculation. Newsweek (Wednesday): CNN (Wednesday): Mad Magazine should run a “Headlines We’re Sure To See” bit on Trump’s arrest. We’ve been here before.