Maybe Wynton for academy coach, because he really does seem to have produced some quality youngsters in recent years through his WYNERs thing BUT is that selection bias? I mean did promising young players choose to go to his academy because of the contacts he has etc and then when they're a bit older it looks like he made them good, when in reality they would have been just as good anyway if they had trained elsewhere?
He seems to clash with too many people to be the 1st team manager IMHO.
And to all the people saying he was a great player - no one is arguing that, but great players do not necessarily make great managers and vice versa. Look at Maradona and the mess he made of the Argies at the last WC... and at the other end of the spectrum Mourinho, who never even played professionally.
I just don't think it's worth getting Wynton's knowledge and contacts in exchange for the dressing room and board room disharmony it may cause.