londonblue
Topgun Pilot
Id say going to Portsmouth would be far more ambitious.
Chesterfield are at their natural peak, but with Portsmouth a manager has a chance to wake the proverbial sleeping giant.
I wouldnt begrudge anyone leaving a small club to go there.
And we all know how the usually works out.
IMO, given the situation at hand, the most ambitious manager would stay at the highest level possible, prove themselves with a "smaller" club and then wait for the offers to come in from a bigger club. If he goes down a level chairman around the country won't know if he can handle a higher level. They may even question whether or not he believes he can manage at a higher level.