It's not true that Doug didn't spend - he just didn't spend what we didn't have, and the late nineties was the time when we had more than ever before so he spent more.
The majority of that money was from the floatation of the club, plus the £12.6m we got for Yorke, as I recall. Where we went wrong was that Gregory spent it on players of a certain age that meant no re-sale value. Merson, Dublin, Steve Stone, etc. What that meant was the funds effectively died and couldn't be recycled through the club.
Where I think MON and Randy got it right is that their big spends were on younger players, such and Young, Downing and Milner. We've already seen the benefit of that with Milner and are about to with Ash. Did they actually spend more than £5m, which is a modest fee in today's market, on a player over 25?