In terms of the player turning into a manager, that can work out (see Chris Powell at Charlton at the moment) but with respect to managers returning to previous seats of glory... I think it's unlikely to be a good move. One of the main reasons for this is that clubs change managers when fortunes are down. A manager of a 'glory days' team is going to be brought back when things are in decline and so, after the usual boost in form at the outset, he is left with a team that will never achieve the same level of success as before.
Couple that with today's lack of patience and, as often as not, they are in and out within 18 months.