(Credit: Imago/Getty Images)

Jack Heath

Thu 21 August 2025 14:28, UK

Tottenham have seemingly missed out on Eberechi Eze to north London rivals Arsenal to join a growing list of players the club failed to bring in.

'Oh Wow. This is all Daniel Levy's fault' - Pundit slams Tottenham chairman after Arsenal hijack Eberechi Eze deal	‘It’s not dead, I expect him to turn up at Tottenham’ – Daniel Levy’s stunning plan revealed	'Here we go' - Tottenham fans explode after Eberechi Eze hijack

Eze was seen waving goodbye to Palace fans in their 0-0 draw with Chelsea last weekend (17 August) with a departure to the Lilywhites seeming inevitable given his signs of a farewell.

After it looked like the deal between Eze and Tottenham was done and dusted, north London rivals Arsenal have hijacked the Crystal Palace talisman and will be taking him to the Emirates.

The Eze in Arsenal colours “Here we go” announcement has left Spurs fans fuming with another comedy of errors from the penny-pinching tactics of chairman Daniel Levy.

Football Insider takes a walk down memory lane at some of the marquee signings Spurs missed out on down the years as they rue yet another missed opportunity, as per The Athletic.

After the arrival of Brazilian superstar Ronaldo, rumours suggested Fernando Morientes was surplus to requirements at the Santiago Bernabeu as the Lilywhites honed in.

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Reportedly, it was understood a fee between £6-7million had been agreed for the Spaniard, an absolute bargain for the forward.

However, Levy supposedly “asked that Spurs pay in instalments, over a 10-year period” as the Real Madrid sporting director put the phone down in anger.

In classic Levy fashion, the north London outfit failed to land a major player to improve their squad as his dire negotiation skills failed the club once again.

A shrewd businessman, sometimes the chairman’s money-saving tactics lost deals (Credit: Imago)

In a strikingly similar fashion to the Eze situation, The Athletic reported that “Spurs were one of the many interested parties and made inquiries” over the teenage sensation.

However, manager of the time Arsene Wenger managed to convince the Saints prodigy to head to Highbury, especially given the supreme stability in the red half of north London compared with their neighbours who were a much poorer side at the time.

The Lilywhites have always been big fans of lifting up youth and this missed opportunity was just another blow in a long list of talented prospects that could’ve gone on to be club legends.

Everyone who watches the Premier League is aware of the outrageous skill of Eden Hazard, who turned defenders inside-out during his time with Chelsea.

Yet, the Lilywhites were allegedly heavily interested in the Belgian when he was at Lille with then Spurs first-team coach Clive Allen deeming the failure to sign him a “regret”.

Allen had spoken to Joe Cole, who was playing at the French outfit at the time, who said: “he [Hazard] was the best player he’d ever played with.”

The Tottenham head coach even met with the chief scout and the Belgian, who was keen on a move to north London, but ultimately joined the Blues, Cole’s former side.

If the club had been more proactive they could have easily tempted the attacking wizard to move to the other side of the capital and saved numerous games of heartache the ex-Real Madrid winger caused.

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This is likely a transfer nearly all Spurs fans are aware of after the Anzhi Makhachkala winger caught the eye of several of the Premier League big boys.

The Lilywhites had seemingly won the race with the South American even undergoing a “medical only for Chelsea to hijack the deal at the very last minute”.

Levy was reportedly “incandescent” with this approach from their London rivals as Willian went on to enjoy several solid seasons in the west part of the capital.

I vividly remember when this saga happened and was completely flabbergasted by the actions of one of of our nemeses who, as per usual, pounced on our club’s appalling transfer management.

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Arguably one of the greatest centre-backs the English top-flight has ever seen, the north London side were a name away from landing the Dutchman.

In the 2014-15 season, Toby Alderweireld joined Southampton on-loan from Atletico Madrid and impressed in a talented Saints side.

Seeing his potential, the Lilywhites pounced on the Belgian who quickly became a club hero at White Hart Lane.

However, it was understood that Virgil van Dijk, then at Celtic, was “the next name on the list of centre-back targets” for the club, marking a crazy football butterfly effect.

Whilst Alderweireld will always have a place in my heart, imagining the towering Dutchman gives me goosebumps, an image and feeling we never got to witness.

Now the centre-piece of Bayern Munich’s defensive line, the France international was once nearly signed by Spurs.

“Spurs’ scouts raved about his athleticism and ball-playing” after he starred for France in the Under-17 European Championship.

“Deemed perfect for the [Mauricio] Pochettino project”, Tottenham were presented with an opportunity to sign the young defender for “£300,000”, an absolute bargain given his growth across his career.

Yet, Red Bull Salzburg swooped in to steal Dayot Upamecano due to their increased purchasing power, rendering the north London outfit unable to match them.

Landing superb youth prospects can be make or break in building a solid foundation at a club and the Lilywhites missed out on a supreme defensive gem.

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The Aston Villa academy graduate had impressed in the Midlands, catching the eyes of several Premier League suitors, including Spurs.

Reportedly, Levy submitted an offer of “£25m” which was completely inadequate for a player of his quality.

In rather comical fashion, the Englishman then joined Man City in the summer of 2021 for a British record-fee of £100m (Sky Sports) as the Lilywhites chairman missed out on an exciting star.

Indeed, the trajectory of the England international at the Etihad can be debated, but the 29-year-old enjoyed an outrageously successful period in Manchester.

I’d also be of the opinion that Grealish is a classic “Tottenham” player in his play style, yet, once more, Levy was unwilling to up his ridiculously low bid.

The Villa starboy nearly went to north London but the offer was way too low (Credit: Imago)

If you ask any fan of the club who is the one transfer they wished would’ve happen, I guarantee Paulo Dybala will always come up as being a hammer blow not to have signed him.

In August 2019, Tottenham had agreed a £64.4m deal with the Argentine (Sky Sports), in a bid to greatly bolster the attack.

The Argentina international was tipped as one of the stars of a new generation, yet, in cruel fashion, Juventus called off the deal at the last second after deciding the striker was not for sale.

In recent history, barring Harry Kane, strikers have been extremely hard to come by at White Hart Lane, especially when signing them.

This includes the long-list of failures such as Roberto Soldado and Vincent Janssen who were unbelievably awful during their time in London.

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