Former Tottenham manager Tim Sherwood has told talkSPORT he had to persuade Spurs chairman Daniel Levy to not sell Harry Kane to Leicester.
The ex-Spurs player and manager was the man to hand Kane his full Tottenham league debut in 2014 following his loan spells at Leyton Orient, Millwall, Norwich and the Foxes.
Since then, Kane – now 29-years-old – has become the club’s all-time top scorer with 271 goals in 425 appearances, as well as being England’s captain since 2018.
But it turns out Kane’s career nearly took a totally different path, as Sherwood lifted the lid on having to persuade Tottenham’s hierarchy not to sell their academy graduate just before his Premier League debut.
When asked by talkSPORT Drive host Andy Goldstein why he handed Kane a chance in the first team, Sherwood said: “I just saw a boy with a lot of ability, but most of all a mental capacity that is second to none.
“[He had] a drive to want to improve and want to earn the opportunity to play in the first team.
“On my watch, he earnt that over a period of a couple weeks I just knew there was no way I could leave him out anymore and I told him he was going to play and the rest is history.”
When asked whether Levy was keen on Sherwood’s plan to start a 20-year-old over experienced strikers Jermaine Defoe and Emmanuel Adebayor, he said: “Yeah but I think it was driven by Franco Baldini who was the sporting director there.
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“I remember telling Harry he was going to play, it was on the Friday before the game against Crystal Palace on the Saturday and [Baldini] asked me to come see [Levy] with him.
“So we sat down and Daniel asked me what the team was on Saturday, so I wasted my time telling him what the back four was and the midfield.
“As soon as I got to Harry he was asking me why certain, more experienced players weren’t ahead of him, and I said he’d earnt the right.”
He continued: “It was a tough conversation, I think Daniel genuinely trusted my judgement on players but he was obviously getting told by someone else this player possibly wasn’t good enough for the Premier League.
“Tottenham wanted players good enough for the Premier League and the Champions League. It was obviously Franco Baldini getting in his ear and telling him he wasn’t good enough.
“They had a bid lined up from Leicester to sell him for £600k which I obviously resisted. There was no was I was letting the boy going for that. He’d have eaten £600k worth of food since joining the club at ten [years old].”
When quizzed on whether Levy was keen on selling Kane on, Sherwood said: “I don’t know if he was prepared [to sell him], but he and Baldini put it to me that this is what was on the table.
“But in the end Daniel had to trust someone, and the trust came from Harry getting in the team and subsequently scoring three in three games.
“I think he realised either the price tag has got to go up or maybe this kid is good enough for the first team and that was the case eventually.”
Tottenham also managed to keep hold of Kane in 2021 when the striker was heavily linked with Manchester City.
However his future now remains uncertain again with his contract expiring next summer.
With no major trophies to his name and the prospect of potentially no Champions League football next campaign, Kane could finally be heading for his first permanent move away from north London.
“I wouldn’t like to make a decision for him,” Sherwood said.
“Harry knows what he wants, he knows himself. If he asked for my advice, I’d tell him he needs to do what’s in his heart.
“If you cut him in half, he’d bleed white.”
But after weighing up whether staying at Tottenham was a risk with him turning 30 this year and titles looking unlikely thanks to the chaos off the pitch at the club, Goldstein then pressed Sherwood on whether he thinks Kane should stay.
After a long pause, he eventually replied: “Yes.”