Jamie Redknapp, who started out at the club's academy before three professional seasons later on in his career, took on chairman Daniel Levy before Spurs faced Manchester United.
The north London side are on course for one of their worst-ever Premier League seasons, 15th in the league and crucially out of both domestic cups.
Manager Ange Postecoglou spoke up his ability to lift a trophy in his second campaign, but those hopes are all but over with Spurs only still active in the Europa League.
With manager after manager failing to end the club's trophyless streak since 2008, ire is now turning on Levy and ownership group ENIC.
Redknapp is one of those, explaining that the fish may well be rotting from the head down when it comes to the club's culture.
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"I've thought about the situation here long and hard since they lost against Liverpool because I played for both clubs," the ex-midfielder began. "I tried to figure out why Tottenham have been underachieving for so long?
"I think a lot of it does come from culture, a winning culture. When I was at Liverpool I didn't win as much as I'd have liked to there but every season the environment was to try and win.
"But here I just think as long as they've got the American Football and they've got Beyonce in the summer, they're happy, the owners are happy.
"It looks like a business model that everyone can be happy with that can be successful. But does that breed a winning environment? No, it does not because something is fundamentally wrong."
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The majority of match-going Spurs fans are seemingly in agreement with their former no.15, with thousands attending a protest ahead of the clash against United.
Should things go sour against the Manchester side, Postecoglou's position will again come under the microscope, and Redknapp can't quite see why he isn't gone already.
When comparing other managers being sacked despite doing better than the Australian, Redknapp explained: "There's never any rhyme or reason when he's [Levy's] got rid of managers.
"When you look at even [Andre] Villas-Boas, he was seventh in the league.
"It's hard to second guess what someone like Daniel Levy will do, he'll look at things and try to assess, but when he comes under enormous pressure that's when he tends to change the manager.
"But he's probably thinking right now, 'who else do I bring in?' There are candidates out there I think will do a great job here, but I think that's the problem."
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