From forgettable loan spells in the English Football League to being crowned the best player in the world, it is little wonder that Harry Kane’s former manager views his historic Ballon d’Or victory as the ultimate modern-day fairy tale.
"This is a Cinderella story we’ve never seen before," ex-Tottenham Hotspur manager Tim Sherwood, who handed Kane his full Premier League debut, tells Sky Sports.
"He keeps breaking records, and I keep thinking, ‘Are we talking about the same kid?’ There was always a chance, because he felt like there was no ceiling—he would always just break through and go further. I mean, not even Harry would say he could believe it, I would suggest."
The Bayern Munich striker’s recent coronation in London made him the first English winner of the Ballon d’Or in 25 years and just the fifth in the prestigious award’s history.
The last Englishman to claim the prize was Michael Owen, who enjoyed a much more straightforward route to the top of the game. Owen won the award at the tender age of 22 in 2001, a mere four years after making his senior debut for a giant club in Liverpool. By contrast, Kane’s triumph has arrived at the age of 33, some 15 years after his tentative first steps in senior professional football out on loan at Leyton Orient in League One.
"I think we have to highlight his journey," says Sherwood, whom Kane publicly thanked on stage during his Ballon d’Or acceptance speech.
"Even when we go back to Michael, he was a superstar as a kid, and he got the opportunities at a very young age at Liverpool, which is a giant football club. Kane came through the hard way, really. He was a player who wasn’t universally loved. He’s not like a Max Dowman, for instance, who is a superstar at 16 years of age. He struggled to get some game time and to get a manager to really, really buy into what he had."
Kane himself openly acknowledged his arduous path to the summit during his acceptance speech in the capital.
"My journey wasn’t straightforward; I didn’t go straight to the top, I had to experience a lot of loan moves and fight my way to get to where I am now," Kane reflected.
For Sherwood, it was precisely those low-key, gritty loan spells at Orient, Millwall, Norwich City, and Leicester City that forged Kane into the world-class operator he is today.
"I hear a lot of people talking about failed loans," Sherwood notes. "We never felt like that because we felt that him playing in Under-21 football was a waste of time. They were really good loans, and those loans were the reason why we’ve got a player like that."
Kane’s ‘Sliding Doors’ Moment
For a long period, Kane was very much out of the cold at Tottenham Hotspur. It was not until Andre Villas-Boas was dismissed and Sherwood subsequently took the reins that a door finally opened for the young forward.
Sherwood handed Kane his first-ever Premier League start—and the then-20-year-old immediately seized the opportunity by scoring the opening goal in a dominant 5-1 home victory over Sunderland in April 2014.
"He wasn’t getting anywhere unfortunately," Sherwood recalls. "He wasn’t around the first-team squad, so I suppose it’s a sliding doors moment that I managed to take over until the end of the season and I managed to give him a stage where he could perform."
And perform he has, on a scale few could have predicted. Kane has accumulated nearly 550 senior goals for club and country, cementing his status as Tottenham’s all-time record goalscorer, England’s leading marksman, England’s top scorer at World Tournaments, and the highest-scoring English player in the history of the UEFA Champions League.
His extraordinary scoring exploits scaled breathtaking new heights during the previous campaign when he plundered an astonishing 73 goals across all competitions. Sixty-one of those strikes came in Bayern Munich colours, leaving him 19 goals clear of any other player across Europe’s top five leagues. In fact, it was the highest single-season tally by any player since Cristiano Ronaldo netted 61 times for Real Madrid during the 2014/15 campaign.
For Sky Sports pundit Jamie Carragher, Kane’s lucrative £100m transfer from Tottenham to Bayern in the summer of 2023 was the catalyst that finally unlocked global recognition and the ultimate respect his talents merited.
"It’s a move he needed to make," Carragher tells Sky Sports. "I thought he might be obsessed with the Premier League goalscoring record, but he’s obsessed with goalscoring records, not just that one. But it also gives him a great chance of winning the Champions League and being involved in Ballon d’Or selections. There’s no way Harry Kane could’ve won the Ballon d’Or if he was playing for Tottenham."
‘Kane is an Example to All Young Kids’
The switch to the Bundesliga has delivered the team silverware that Kane so desperately craved throughout his career. Despite capturing three Premier League Golden Boots with Tottenham and breaking the club’s goalscoring records, individual accolades were never the primary motivation, according to Sherwood.
The lengthy trophyless period in north London ultimately drove Kane to seek a fresh challenge in Germany, where he has since secured back-to-back Bundesliga titles and a German Cup.
"The boy loves Tottenham," Sherwood says. "He wanted to win there, but he was winning individual accolades at Spurs, and it wasn’t enough for him. When we all grow up, we all want to be footballers, and we don’t want to be footballers because we want to be rich. There are possibly some players like that now, but that certainly wasn’t his motivation. He wanted to go to a team that could win, and he picked Bayern, and we have to say it’s been a good choice."
Sherwood adds: "He’s a 100 per cent team man. If I told you he would rather win the Champions League and the Bundesliga title than the Ballon d’Or for himself, that would be the truth. Not every player would say that, but I genuinely believe that that is the measure of the man and that’s what you’re talking about, and that’s why he’s such a dream to manage. The work rate and the example he shows to any young kids coming through, and to genuinely go around the houses to try and make it, and he certainly made it."
Is Kane England’s Greatest-Ever Player?
Kane continues to rewrite the record books in German football. He stands as the fastest player to reach 100 Bundesliga goals, holds the record for the most goals in his first 100 Bundesliga appearances, and is the fastest player to register 100 goal contributions in the competition.
It is statistics pertaining to his overall play, however, that prove Kane is far more than a conventional penalty-box poacher. His exceptional vision, tactical awareness, and sublime passing range elevate him into an elite playmaker. This multifaceted ability was vividly displayed during Bayern’s 2-2 Champions League home draw against Arsenal, where Kane frequently dropped deep into midfield before executing a magnificent, pinpoint pass from the center circle to set up Alphonso Davies for an equalizer.
His creative output has been evident for years; during the 2020/21 Premier League campaign with Tottenham, Kane claimed the Playmaker of the Season award for registering the highest number of assists in the division.
Yet, when considering whether his comprehensive skill set, records, and now a Ballon d’Or crown make him England’s greatest-ever player, Carragher diverges, pointing toward another English Ballon d’Or laureate.
"I would still always put Bobby Charlton as the greatest England player ever," he says. "He’s won the World Cup. He’s won the Champions League with Manchester United. As a midfield player, he was the leading goalscorer for a very long time for both United and England. I’d still always say Bobby Charlton, because right now this England team, even though it’s been a golden period for us, Harry Kane and the others still haven’t got their hands on a trophy, and that’s what Bobby Charlton did."
Could Kane Return to Spurs?
As Kane closes in on becoming England’s most-capped player of all time, questions naturally linger over his long-term future. While there are still plenty of trophies to contest abroad, Sherwood believes another historic milestone might eventually lure the striker back to his homeland.
"I believe he will come back for that individual accolade to be the Premier League top scorer in the future, maybe in a couple of years’ time," the former Premier League-winning captain suggests.
Kane currently sits 47 goals behind Alan Shearer’s long-standing all-time Premier League scoring record of 260 goals.
"He will only come back to a team he believes can win," Sherwood continues. "At the moment you’re looking at Man City with the troubles they’ve got, so Liverpool possibly, that could be a chance for him. Tottenham could be in the frame if they start progressing. Manchester United could be in the frame, but they’ve got a long way to go to prove that they can win anything as well. I’m not sure it’s ever going to be Chelsea or Arsenal because of the Tottenham connection.
"So, it’s on a positive note for Tottenham fans if they can start progressing and you can prove to him that he can come back and he can possibly have a good chance of winning at your club as he will have at Liverpool, Man Utd and Man City—but we don’t know what’s going to happen with them—then there’s an opportunity he might come back and see out his career where he started it."
It would provide a remarkably fitting final chapter to Kane’s extraordinary footballing journey.