Geoff Nulty
Player Valuation: £950k
I think to dominate for a long period of time, over more than one cycle of a squad, you need quality off and on the pitch and not sure we ever had that since Moores (which was before my time). The 80s success was down to Kendall 100% so regardless of what might have happened without a European ban, once he stepped down it was only ever going one way. There wasn't that leadership on the board for sustained success.
Seemed like a lot of stuffed shirts running the club at that time - Sir Philip Carter was a good clubman and a respected voice in the league, but it needed someone way more dynamic to take the reins at that time.
The prem was a bit of a slow burner, as well, IIRC - people talk about it now like 1992 was some sort of year zero, the day the money faucet was turned on. But it took a while to get going which makes it all the more aggravating to have missed the boat - it needed ambition to borrow money and think big like you say, but it wasn't like a wild 100-1 shot that needed a crazed visionary to see.
The complacency and inaction stretches back into the Moores era, too. I've long believed this to be the case, and reading Gavin Buckland's new book - Money Can't Buy Us Love - just confirmed it for me.