England greats Jamie Redknapp and Jamie Carragher believe Tottenham "won't ever win anything" as Ange Postecoglou battles the brutal realities of his side's inconsistencies.
Spurs fumbled a 2-0 lead against Chelsea on Monday (AEDT) at Tottenham Stadium, with two Cole Palmer penalties handing the visitors a 4-3 win.
Postecoglou's men gave him the dream start he needed to briefly silence the critics, with Dominic Solanke and Dejan Kulusevski netted early goals in the opening 10 minutes.
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But the two-goal cushion did not survive as long as all hoped as Jadon Sancho smashed the ball into goal in the 17th minute.
The slight shift in momentum made for an entertaining contest for the remainder of the opening half, but Tottenham struggled to establish a strong sense of control on return.
Palmer extended Chelsea's lead three via penalties following reckless challenge attempts from Yves Bissouma and Pape Matar Sarr, while Enzo Fernandez found the net to bring their score to four.
Son Heung-min slotted a late goal in the 96th minute but his efforts were not enough to cover the fact his team has won just one in their past seven games.
Son Heung-Min of Tottenham Hotspur and Moises Caicedo of Chelsea compete for the ball.
Son Heung-Min of Tottenham Hotspur and Moises Caicedo of Chelsea compete for the ball. Getty
Redknapp, a former England star, insisted Spurs need to recognise the easy target they present to teams if they wish to stand any chance of returning to challenging the title.
"You can't say that they ever looked comfortable. They are just too easy to play against," he told Sky Sports.
"It could have gone either way. It was chaotic.
"When you play against Tottenham, because of how ill-disciplined they are with and without the ball, they give you so may chances.
"If you are having a bad run, Tottenham are the perfect team to play.
"No one was sitting here with conviction that they were going to hold onto a 2-nil lead because of how open they play.
"There are times of pure joy, like when they played Man City and won 4-0. You think, 'oh, this could be the turning point' but then they just disappoint you again.
Sky Sports presenter Jamie Redknapp.
Sky Sports presenter Jamie Redknapp. PA Images via Getty Images
'Right now, Tottenham need to win a trophy," Redknapp continued.
"That is more important than anything else right now because that is the stick they always get beaten with."
Redknapp noted that teams like Ipswich and Crystal Palace had yet to achieve a victory in the Premier League this season until they faced Spurs - a fact which rattled many of the club's fans.
But the onus on Postecoglou's coaching style is not the only thing to blame, according to Carragher, who raised questions about the future of Tottenham owner Daniel Levy.
In 23 years of ownership at Spurs, Levy has witnessed 14 managers in the top job.
"Tottenham are so close to being a good side but they always let you down," Carragher said.
"If you want to be entertained come and watch Tottenham. I don't think they'll ever win anything but you'll certainly enjoy yourself.
"What Daniel Levy has done here in terms of the training ground and the facilities (is great). For me, I don't think there is a better stadium in the world. That has been Daniel Levy's strength.
Ange Postecoglou, Manager of Tottenham Hotspur, reacts during the Premier League match between Tottenham Hotspur FC and Chelsea FC.
Ange Postecoglou, Manager of Tottenham Hotspur, reacts during the Premier League match between Tottenham Hotspur FC and Chelsea FC. Getty
"But it might be a time for Daniel Levy, who I've been a supporter of because look at the work he has done, it's probably time for someone else to come in.
"To not win a trophy in that period of time with the managers they've had, they've never really gone out of their way in the transfer market, the wage bills are always the smallest.
"But now that (Levy's) work is done in terms of the stadium and a training ground, someone else needs to be in charge of this football club.
"If he has had that many managers, he is not making the right decisions. No one in this country ever expects Spurs to challenge for the title.
"We think it's a mentality thing but how could Arsenal have done it without going crazy spending wise and Tottenham couldn't when they were competing with them."
Postecoglou will face off against former Scottish rivals Rangers on Friday in the Europa League.