Chris Waddle has given an honest verdict on Antonio Conte, what Daniel Levy needs to do to keep him in north London and when he thinks improvements will be seen.
Tottenham have produced a mixture of performances and results under the Italian so far and already experienced on transfer window.
The winter window saw four first team departures and just two arrivals, after Spurs were linked with a number of players who made the move elsewhere.
The Lilywhites now sit seventh in the Premier League, five points off fourth-placed Man United and with two games in hand.
Former Tottenham player Waddle has admitted that he believes it could still be a while until normality is fully resumed, after the hardship of the pandemic and this could cause uncertainty over Conte's future at the club.
"I think Tottenham was going the right way and I thought great training ground, fantastic stadium, everything was going in place. They had all these NFL games come in, boxing, rugby. They were taking money, and then Covid hit....I think it set them back another two years," Waddle admitted in an interview with Compare.bet.
"Realistically I think this season, next season is going to be difficult still for them and I think maybe the season after that, when everything is back to normal hopefully, I think you will see Tottenham then be in a good position to strengthen, to buy top-class players, not sell their top-class players.
"Whether Conte wants to hang around for two-and-a-half more seasons, I don’t think he will," he added.
Before Nuno Espirito Santo was appointed, the 52-year-old was linked with a managerial move to N17, but he wasn't quite ready to make the move.
The final straw for the Portuguese head coach was the 3-0 defeat to Man United, who were also having their own managerial issues and had been linked with Conte.
Spurs came out on top and the Italian made the move back to the capital in November.
However now he has been in the job a few months, it is clear that there is a lot of work to do both on and off the pitch and he needs backing from the likes of Daniel Levy and Fabio Paratici to help him take the squad to the next level.
If the ex-Chelsea boss isn't given this support then he has shown previously that he isn't afraid to walk away and the 61-year-old has given his verdict on what could be to come for Conte.
"I think Conte is a good manager," Waddle said. "He’s proved that, but he likes to get a strong team. He likes to spend money. He likes to get good players like Pep [Guardiola] has got and like [Jurgen] Klopp has got.
"I think he’ll stay until the end of the season now, but listen. A lot of clubs will give him offers," he added.
"It could be Man United, for all we know. It would be tempting, because Man United do spend money, so he might think, ‘Yes, I can turn Man United around, because I’ve got a cheque book which I can go and spend.’" Waddle said.
"Will he be lured back to Italy? Spain? There are a lot of big clubs around the world who wouldn’t be frightened to back his ideas in the transfer market and buy quality players and go and win, because he proves he can do it, but you’ve got to say, he needs a cheque book.
"He’s looked at Tottenham and he’s thinking, ‘Yes, we’ve got some good players, very good players, but overall, we’re not as good as Liverpool. We’re not as good as Man City. We’re not as good as Chelsea,’ and that’s where he wants to be," he added.
"If Tottenham can say, ‘No, in the next two years or two-and-a-half seasons, we can’t get near them on demand of wages, transfer fees,’ that might turn his head and think, ‘I don’t want to finish fourth, fifth, or sixth. I want to be first.’ If he doesn’t see that ambition with Tottenham, I think he’ll move on."
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This is why the summer transfer window is such a pivotal one for Spurs and if they aren't able to show their ambition through transfers and back Conte, it will be difficult to keep him in N17.
In January, Tottenham missed out on the likes of Adama Traore and Luis Diaz and will need to recruit quality players to help upgrade their current squad in various areas.
If the Italian's wishes aren't fulfilled by those above and he is made offers from other clubs that will grant his wishes, as Waddle alludes to, then what will keep him at Spurs?
Not only do the Lilywhites need to continue their fight for a top four spot in the final few months of the season and progress as far as possible in the FA Cup, they then need to put the hard work in during the summer to strengthen the squad in time for the 2022/23 campaign.
