Before the international break, Spurs hadn't conceded a goal and managed to keep star player Harry Kane. However, since all the teams returned, they have since then suffered heavy defeats to Crystal Palace, Chelsea and fierce rivals Arsenal.
Pressure on Nuno Espirito Santo is increasing but the 'stubborn' Daniel Levy is to blame, believes Crook, who criticised the Spurs chairman's stance on keeping Harry Kane at the club.
"What Tottenham have done, out of pure stubbornness from Daniel Levy is keep a player against his will, and at what cost?
"This squad, it looks tired, it looks like it's in need of an overhaul, it looks like a number of players who probably don't want to be there, you might even put [Tanguy] Ndombele in that list as well and they're going backwards.
"Yes they've kept the England captain, one of the greatest goal scorers in the history of the Premier League but the whole picture looks a lot bleaker from making that decision.
"They should have sold Harry Kane, bought in three or four players like Aston Villa [when selling Jack Grealish] have and made the squad more competitive.
"What they also should have done is have a plan when they fired Jose Mourinho and in the end not go down to number seven or eight on the list and hire Nuno Espirito Santo, a manager who was basically fired by Wolverhampton Wanderers."
Over the summer transfer window two of the biggest names in football were Jack Grealish and Harry Kane were linked with moves away.
The former's old club received £100 million from Manchester City and reinvested it into signing Danny Ings, Leon Bailey and Emiliano Buendia.
Meanwhile the latter kept their player and it looks like they might have been better off following Villa's approach instead.
Meanwhile the latter kept their player and it looks like they might have been better off following Villa's approach instead.
For now though, until the January transfer window at least, Kane, Spurs and Levy will have to mend their relationship and help Nuno achieve some much needed wins.