He's a media personality and one of the best pundits in England, while having played the game itself. He certainly has some kind of idea of the ins and outs at a club like Arsenal. Not as much as someone like Henry, but I think enough to have a fair opinion on things from the outside.
That's true, though I think Robbie is also the most honest of these people and you can't blame him after being given such a chance. That being said I think it's a bit of a shame for such a channel to be dependent on the characters they have to really become successful. The idea is right but it doesn't help the format at all having them shout at each other week in week out to become relevant.