Absolutely agree with the above. Although founder members of the PL we as a club were waging internal battles - see the Scholar bankruptcy, sale of club to Sugar, then the subsequent Sugar v Venables court case. By the time the dust settled on all that we THFC were miles behind...
To make matters worse Sugar, despite (or perhaps because of) his bluff & bluster, rags to riches schtick was the wrong man at the wrong club. Small time.
My old man was part of the coaching set up at the club. At a meeting Sugar asked why Spurs couldn’t be more like Wimbledon - buy low sell high? The staff were shocked and concerned to say the least. His right hand man, Claude Littner stopped the staff having biscuits - they had to buy their own..
I don’t need to remind supporters of the embarrassing Armstrong / Bergkamp comparisons, ‘Carlos Kickaball’ utterances or washing cars with players shirts.
The club was a mess for many years. Reactionary appointments (Woolwich have Wenger, we’ll get our own in Gross) and terrible player signings.
TBF Enic/Levy continued this trend for more than was necessary or bearable. The current trajectory, for me, began with Harry, went back a few steps with Tactics Tim and AVB, soared upwards under Poch and hopefully Mourinho can put some icing on the cake.
Don’t underestimate the damage caused in the 90s though...
I think you have to give Jol a bit of credit because he did a very good job with an average set of players before Ramos ruined everything (cheers for the trophy, though), but definitely agree that our doldrums during the 90s have been a massive handicap. We still have a dodgy reputation because of all those years of being repeatedly whipped by the big boys while absurd shit like lasagnagate was happening to us. We have made massive strides but hopefully we are nearing the summit now.