Glenn Hoddle won plenty of trophies as a player with Spurs and Monaco, but the league title is the one that got away.
The former Tottenham and England manager knows what it’s like to finish in the upper echelons of the table, leading the London club to three top-four finishes in the old First Division.
He played at a time when the Merseyside clubs were dominant, and knows how important it is to seize chances to break that kind of dominance when they come along.
With that in mind, he acknowledges that his old club will never have another chance as good as this to lift the Premier League trophy.
Speaking to JOE ahead of Tottenham’s FA Cup fourth round meeting with Colchester United, BT Sport pundit Hoddle pointed to the disarray suffered by more established teams this season.
“Other teams will build in the summer, Chelsea can sort themselves out and get players back together – an opportunity like this might not come again,” he said.
“They have a squad that can do it, they’re contenders for the title, and in the end it comes down to whether they believe they can win it.”
Spurs are just five points behind league leaders Leicester City, and had they beaten the Foxes at White Hart Lane – instead of losing to a late Robert Huth goal – they’d be top.
Hoddle suggested back-up for Harry Kane is the only area in which the club is really lacking, although he noted they would need to make good use of their squad in the absence of injury victim Jan Vertonghen.
He admitted that, while January is “a tough time to buy,” manager Mauricio Pochettino may regret not moving for one player who has switched clubs during this window.
“Charlie Austin is one who maybe slipped through the net for them, even if it was just on a six-month loan deal,” he said, suggesting it now comes down to “whether Son can play there, or whether they can do what others do and play without a striker.”
As for their chances on other fronts, Hoddle remains convinced that the squad is strong enough to compete.
“I think they’ve got the squad to take on the trophies that they are in at the moment, obviously the Europa League and they’re well placed in the league,” he said.
“They are playing well enough and got a great history in the FA Cup and something the fans adhere to. They are well capable of winning it but obviously they have got a tricky tie thought at Colchester.”
Watch Colchester v Tottenham in the Emirates FA Cup fourth round live and exclusive on BT Sport 2 from midday this Saturday. Visit btsport.com for more info.