Spurs have continued to splash cash across recent transfer windows, but are seeing little return on sizable investment. Too many players on their books have struggled for form and fitness, leading to a humble tumble down the Premier League standings being taken.
Ange Postecoglou did deliver long-awaited silverware in 2025, as a Europa League triumph brought a 17-year barren run on the trophy-winning front to a close, but said success only served as paper over some alarming cracks.
Having finished 17th last season, there remains the very real possibility that Tottenham could slip even further this term and through a trapdoor that leads into the Championship. Fate, heading into a final day showdown with Everton, remains in their own hands and heads remain just above water for now.
If Roberto De Zerbi can complete a scramble towards top-flight safety, then plans for future growth can start to be pieced together. Domestic rivals United have shown what can be achieved when surging from 15th to third in the space of 12 months - with Champions League football back on the agenda at Old Trafford.
Could Tottenham stage their own resurgence in 2026-27? When that question was put to Hutton, the former Spurs defender - speaking exclusively to GOAL courtesy of Uudet Kasinot - said: “From what I've seen this season, I don't see it.
“I might have said the same thing against Manchester United but they seem to have really galvanised and come together under Michael Carrick.
“It's going to be an interesting summer for them [Spurs]. I think the injuries haven't helped this season and everything that's happened. They've struggled at home but I don't see them challenging for top four next season, if I'm honest.”
Having worked through three managers since parting company with Postecoglou - in the form of Thomas Frank, Igor Tudor and De Zerbi - change is now required on the field if Spurs are to dispose of their pretenders tag and become genuine contenders once more.
Talk is cheap, but ambitious signings are not. Vast sums of money will be required in order to make Tottenham competitive at the business end of the Premier League table, and said cash may be in short supply.
Asked if elaborate spending will be required in order to turn Tottenham around, Hutton added: “Huge money, absolutely huge. I think this has been the Achilles heel for a number of years where they have gone out and spent a decent amount of money but I just don't think they've got it right.
“The numbers that they're spending, £50-60 million, on players that are not maybe really hitting the heights or not hitting the ground running has definitely hampered them this season.
“Again, the injuries haven't helped but I think when you look at the squad in general, they've just not hit the form. Is that because of pressure? Is it a mentality thing? I'm not so sure but that's two seasons in a row now where it's been disappointing finishes in the league and the fans demand more so it's about having a squad that can deal with it.”