Speaking exclusively to Genting, Sheringham said: “Without a doubt, if you look at hindsight, then you would say it looks like they should have done the business.
“But that’s probably why he [Levy] is a ruthless businessman because he said, whatever the figures were, if they were offering £150m and he wanted £170m, that’s the way he’s done things in the past.
“And you’ll know, the next time that they want someone, if Liverpool want Son next and they offer £120m and he says £140m, you know he means £140m, because that’s the way he works.
“But I’m sure, with hindsight now and the performances, if you could say, ‘Look, take it back and we’ll take that £150m, because I don’t want a player that will under-perform and (is) possibly pulling everybody else down,’ it’s a situation that probably Levy didn’t envisage that was going to happen.
“Hindsight is a wonderful thing.”
Talking From Experience
When Sheringham himself left Spurs for Manchester United, he had an infamous run-in with then-chairman Alan Sugar.
So from personal experience, he knows there might be a difficult few months ahead for their star striker and chairman.
“I think everybody’s surmising about what the relationship is, maybe it’s not as bad as has been suggested,” he said.
“Maybe Harry’s just having a downturn in his performances and that’s where he’s at, who knows? Only those two know about the ins and outs.
“But from an outside opinion, that’s all we can go on – it looks like he’s been given assurances that he could go if the right money came in.
“From Kane’s interviews that he did, saying that he’d love to play with the likes of De Bruyne, I’m amazed that he didn’t go.
“He looks like he’s got the hump that he didn’t go, and that drains on your performances when you are not happy with something.
“I’m sure he doesn’t mean to be playing the way he’s playing at the moment.”
Impact On The Squad
With just one goal and one assist in the Premier League this season, Kane is well down on the levels we have come to expect from him in previous campaigns.
And Sheringham believes that having an unhappy and underperforming Kane could also be affecting the rest of the squad.
“He’ll have a massive influence, I can’t ever imagine him being a bad apple around the place, around the football club, (but) his whole demeanour is powerful,” he explained.
“For him not to be like that will have a big effect on the rest of the players because they look up to him.
“And if he’s not happy it brings other people down, and I think that’s probably worked against Nuno [Espirito Santo] in his short tenure.”