It seems the obvious solution for both Kane and United. Kane approaches his 30th birthday in July still waiting to win his first major trophy, while United have made a proven goal scorer their No. 1 summer target as the key piece in the jigsaw that will make the club Premier League title contenders again.
Kane and United would appear to be the perfect fit, but sources have told ESPN that the prospect of dealing with Spurs chairman Daniel Levy in order to negotiate a deal for the England captain has left United focusing on alternative options including Napoli's Victor Osimhen and Juventus forward Dusan Vlahovic. Despite Kane entering the final 12 months of his Spurs contract this summer, one source has told ESPN that United will not risk a prolonged pursuit of Kane that drags out until final hours of the summer transfer window.
"United can't afford to start the season without a new striker," the source said. "And having dealt with Levy in the past, they don't want to go through that nightmare all over again for Kane with so much at stake, so they might not even get involved."
There are two sides to Levy's reputation as a formidable negotiator, however. Clubs trying to sign Spurs players find Levy, 61, who is the Premier League's longest-serving chairman, having been appointed in 2001, to be obstinate and difficult. But for his employers, he is the man who resisted Manchester City's attempts to sign Kane in 2021, secured a world-record £85 million fee for Gareth Bale from Real Madrid in 2013 and forced United to break their own transfer record in a £30.75m deal for Dimitar Berbatov in 2008.
After signing the Bulgarian striker just minutes before the deadline, a former United executive told ESPN that manager Sir Alex Ferguson and chief executive David Gill vowed never to deal with Levy again -- a pact they honoured until they both retired five years later.
"Daniel was determined that he wouldn't do a deal unless the fee started with a three," the former executive said. "Months of negotiation came down to the final minutes of the window and Sir Alex and David Gill never forgot that."
Fast forward 15 years to summer 2023 and United would be facing the same scenario if they identify Kane as the solution to the team's goal-scoring problems. Only Marcus Rashford, with 14 goals, has hit double figures in the Premier League this season; next up is Bruno Fernandes with five goals.
Since signing Robin van Persie from Arsenal in 2012, United have consistently failed to solve their centre-forward problem. Zlatan Ibrahimovic and Cristiano Ronaldo both scored goals but were in their mid-30s when they arrived, while Radamel Falcao, Edinson Cavani, Odion Ighalo and Wout Weghorst were nothing more than sticking-plaster signings, to varying degrees of success. Romelu Lukaku was expected to be the answer when he signed from Everton in 2017, but he was gone within two years after failing to live up to his initial £75m transfer fee.
If Kane does join United, he would be 30 before he even kicked a ball for the club. But Van Persie was a similar age profile when he arrived at 29, and the appeal of signing the Spurs forward is that he could be a catalyst for a title challenge, just as Van Persie proved to be. But Levy knows United are desperate for a striker, so it is inconceivable that he would choose not to exploit their weakness by demanding a huge fee for Kane -- a fee United would be unlikely to pay due to Kane's age, contract situation and the club's battle to comply with Financial Fair Play (FFP) regulations.
If the player himself were to force the issue by going public with a desire to leave, it might unlock the door to a move, but United simply cannot wait until late summer before signing a striker.
In the middle of this is Kane, a player who has given incredible service to Tottenham and remained loyal to the club much longer than many of his contemporaries would likely have been. He has broken Tottenham's all-time scoring record of 266 goals this season. But he will have seen lesser players at rival clubs win multiple trophies elsewhere and he is a player whose career deserves a silver lining. His dilemma is clear -- stay at Spurs and try to win that trophy, force a move or run down his contract and leave as a free agent in 2024.
There would be no guarantee of success at United, but despite the club's struggles over the past decade Kane's England teammate Rashford has won four major trophies since breaking into the team in 2016. He could win another two this season, with United still chasing the FA Cup and Europa League, having already won the Carabao Cup.
Some clubs find a way to win; others never seem to be able to cross the finishing line first. Spurs have proved to be the latter, even with Kane scoring goals so consistently.
Bayern Munich, yet to replace Robert Lewandowski, have a long-standing interest in Kane, while his pedigree would always appeal to the likes of Real Madrid, Barcelona and Paris Saint-Germain. But those clubs are all more likely destinations next year, when he would be a free agent, rather than in a summer when Spurs could demand in excess of £100m for their star player. Playing overseas would also end Kane's chances of breaking Alan Shearer's Premier League record of 260 goals -- Kane now has 203 following his brace in Saturday's 3-1 win over Nottingham Forest.
If Kane decides to force a move this summer, United would appear to be the obvious destination. But both Kane and United know that Levy will make it hugely difficult and potentially impossible. Something, somewhere, needs to give, but it won't be Daniel Levy.