Despite having overseen another positive season with Spurs which has delivered a top-four finish and Champions League qualification, questions are being asked of Pochettino’s future.
He has dropped subtle hints during the 2017-18 campaign that he could soon be heading for pastures new, and some reports have suggested that he could cross London to succeed Antonio Conte at Stamford Bridge.
Former Blues striker Cascarino admits such an appointment would be “a massive coup” for Chelsea, but doubts it will happen as Spurs would be left “absolutely devastated”.
He told talkSPORT: “Could this be worse than Sol Campbell going from Spurs for Arsenal?
“I feel a lot of Tottenham fans would think it was. Their manager! All he has done over the last few years at Spurs, he’s created a fantastic team.
“If he went across London to a club like Chelsea, supporters would be absolutely devastated.
“Considering what he’s done at the club, I think they would be so upset.
“The throwaway comment that Poch made a few weeks ago, ‘With me or without me’, that says a lot. Why would you say that?
“One thing is clear, Chelsea will see this as an opportunity for a big coup of taking a manger they really believe would take the club in a new direction.
“Poch has got a fantastic record, he has nowhere near to funds that have been available at Chelsea, so I could see that making a lot of sense.
“It would be a massive coup for Chelsea.”
He has turned Spurs into top-four regulars while also helping to smooth the transition into a refurbished White Hart Lane following a season-long spell at Wembley Stadium.
Speculation regarding moves elsewhere is nothing new, with the likes of Paris Saint-Germain and Real Madrid having been linked with his services in the past, but there will be a few high-profile posts up for grabs this summer and Tottenham will be desperate to ensure their Argentine head coach does not fill them.