Mauricio Pochettino is interested in working with Harry Kane again if he's appointed by Tottenham's rivals Chelsea - giving Manchester United a transfer headache.
Erik ten Hag's side are the frontrunners to sign Kane, 29, from Spurs this summer. The England captain has just 14 months left on his existing deal and is being tipped to leave Tottenham in pursuit of a maiden major honour, with United plotting an £80million bid.
Pochettino, meanwhile, is in advanced talks to become the next Chelsea manager, despite being regarded as one of Tottenham's greatest ever coaches. It's believed the Argentine will check if Kane is up for joining him at Stamford Bridge in a controversial move.
As reported by the Daily Mail, Pochettino remains a huge admirer of Kane and could table an offer if given the budget by Chelsea. Kane established himself as one of Europe's best strikers under Pochettino, who was in charge of Tottenham between 2014 and 2019.
A move to Old Trafford is expected to be Kane's preferred option for a number of reasons. Firstly, moving to Chelsea would tarnish his legacy at Tottenham due to the rivalry between the two clubs. Kane is Tottenham's record scorer with 274 goals to his name.
Secondly, Kane wants to become the Premier League's record scorer. Alan Shearer is the current record holder with 260 goals, with Kane on 207 strikes. The latter admitted last month: "I'm getting closer, so it's for sure something I want to achieve." As such, a move abroad seems unlikely - although Bayern Munich and Barcelona remain interested.
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The problem for Kane and United is Tottenham chief Daniel Levy, who is renowned for being a tough negotiator in the transfer market. He values Kane at £100m, with United willing to walk away if Levy wants to spend the summer thrashing out a deal.
There's every chance United will move on to an alternative target if Tottenham don't accept a bid in the region of £80m before United's pre-season tour gets underway in July. Ten Hag wants his squad to be assembled nice and early this summer.
United have learnt from the lessons of last summer, when they spent weeks chasing Frenkie de Jong's signature to no avail. There are other, younger names on their striker shortlist - including Benfica talent Goncalo Ramos, 21, and Napoli star Victor Osimhen, 24.
United are willing to walk away, but Chelsea may not be. They have been the biggest spenders in Europe since Todd Boehly's consortium completed a takeover last summer - investing nearly £600m in fresh talent - and may keep on spending for a while yet.
Like United, Chelsea are on the hunt for a new striker. As Pochettino knows, a player of Kane's quality would improve their struggling squad. The Blues are 11th in the Premier League table and could miss out on a top-10 finish for the first time since 1996.
Levy could pocket a fortune from Chelsea, but selling Kane to a London rival would be a huge risk. Levy is already unpopular with Tottenham's fanbase and such a sale could weaken his position further. Stranger things have happened in football before, though.