Did you? That was at the very end, after he'd insisted T-Mobile was wrong about when his contract was ending, and had emailed the CEO about it, only to be told again that he was wrong.

Why would a reporter call customer service to ask whether he could switch plans? Wouldn't he look at his contract?

It's ok to ask the other party to modify a contract. The other party is under no obligation to do so, but sometimes doing a modification makes sense.