Tottenham Hotspur boast an academy rich with talent, with their most famous product having recently departed as a legend of the football club.

Harry Kane, who worked his way into the first team after numerous loan spells and fine youth-level performances, grew from a nobody into one of the finest finishers in Premier League history.

In fact, he departed north London having scored 278 goals in 430 games for the Lilywhites, with his tally in the English top flight only bettered by the record-holder Alan Shearer.

Pundit Jamie O'Hara would rush to praise the legacy left by the England captain back whilst speaking to talkSPORT, who joined Bayern Munich for a mouth-watering £100m sum in the summer: "I’ll put it out there; I think he is the greatest striker English football has ever produced. He’ll get 70 goals for England. He will break the Premier League record. How can we have any negativity whatsoever towards a man who’s got everything?"

Although that latter record now seems likely to remain intact, the former Spurs midfielder would continue: "What he’s done lasts forever. He is immortal in the game of football. You are always going to remember Harry Kane for what he achieved for Tottenham, for England and in the Premier League."

The 30-year-old is not the only man to have earned success after graduating from their academy though, with lesser names such as Kyle Walker-Peters, Harry Winks, Oliver Skipp and Peter Crouch showcasing enough talent to shine around the pinnacle of English football.

However, when it comes to players Spurs have produced, only Ledley King really comes close to Kane with regard to quality and the lasting memory his presence at the club left behind.

How good was Ledley King?

Emerging into the senior squad in 1999, the domineering centre-back quickly established himself as a mainstay in the starting side, although he was initially deployed in midfield.

It was perhaps this stint in the engine room that gave him such prowess in possession, which when blended with his freakishly powerful physique, made him unstoppable at times throughout his career.

A true one-club man, the 42-year-old would enjoy his entire career in north London, amassing 322 appearances and winning a sole major honour. However, many will look back on King's career with sympathy, given the injury woes he suffered.

In fact, during one stint the defender was forced to undergo separate training sessions to manage a longstanding knee ailment, with manager Harry Redknapp labelling him "an absolute freak" for his ability to perform at such a high level despite a lack of midweek activity.

This was one of the numerous glowing testimonies that have come the way of King, the likes of which journalist Darren Lewis sought to supplement: "It is no exaggeration to say that on his day he would have walked into any Premier League team in the country. Yes, he was that good," he wrote.

Then, former teammate Dimitar Berbatov would weigh in, comparing the former England international with some of the Premier League's greatest within his role: "For me he was up there with [Nemanja] Vidic and Rio [Ferdinand]. He was so intelligent and read the game so well. He was always intercepting balls purely because he knew where the striker would be."

King was a true mountain of a centre-half, and clearly a devastating opponent to face when fit. As such, it should come as no surprise to see The Times include him within the top 25 on their list of Spurs' players of all-time, comprised in 2009.

He will forever remain a cult hero at the club, and yet Mauricio Pochettino arguably had an opportunity to secure his clone in 2015. A Rolls-Royce in possession, but boasting a hulking physique and a blistering turn of pace, had they signed Virgil van Dijk when they could have all those years ago, perhaps King's legacy might not be as strong as it is today.

Did Spurs nearly sign Virgil van Dijk?

Since moving to Liverpool, the classy Dutchman has earned some of the highest praise seen in recent history for someone in his position.

With Rio Ferdinand suggesting he was the best centre-back on the planet as of May 2022, former Ballon d'Or winner Michael Owen would then claim: "Well, I go further, I think he's the best centre-half of all time."

So, to think that the Lilywhites had him on their list of potential signings around the time they swooped for Toby Alderweireld is incredible to think about, as they were so close to achieving greatness.

In an article by The Athletic, they would write about that interest: "Interestingly, in the summer of 2015, when Spurs signed Alderweireld, Southampton replaced him with Van Dijk. Had Levy failed to get Alderweireld then Van Dijk, then at Celtic, is understood to have been the next name on the list of centre-back targets."

However, their indecision cost them, still unconvinced by his performances for the Scottish champions: "Van Dijk’s performances in Scotland were excellent but there is always a question mark over whether players can make the step up from the Scottish Premiership to the Premier League."

The 32-year-old has since gone on to play 227 times for the Reds following his £75m switch, with his acquisition the catalyst that ushered in unparalleled success for Jurgen Klopp.

With the 58-cap international at the back, they have since won the Champions League, Premier League, FA Cup and EFL Cup, with Van Dijk instrumental in all of them. The former competition was even won at Spurs' expense, as the defender earned a clean sheet in the final against Pochettino's men.

His German manager would add to the rich list of praise afforded him, building on the "monster" label that Gary Neville handed him: "He’s so important for us, not only as a player but as a person as well. I couldn’t say a bad word about him even if I wanted to."

Whilst King remains a huge favourite for Spurs, had they signed Van Dijk, perhaps under Pochettino they could have instead been the side to earn such success by claiming the elusive silverware they continue to strive for.