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Where has it all gone wrong for Tottenham?

Every few years, a team seemingly “too big to go down” gets dragged into a relegation battle. Invariably, they find they’re not too big to go down.

Leeds in 2004, Newcastle in 2009, Aston Villa in 2016. Of course, none of these happened in a vacuum, but were the consequence of years’ worth of bad decisions, and Tottenham may be about to follow them.

Leeds chased the glory of the UEFA Champions League and paid the price. Financial mismanagement led to relegation, administration and two decades in the wilderness.

Newcastle never quite recovered from parting ways with Sir Bobby Robson. The steady decline continued under Mike Ashley, with the marquee signing of Michael Owen spectacularly backfiring. Alan Shearer’s departure was later felt and following chaos in the dugout in the 2008/09 season, the Newcastle hero regrettably took them down.

Villa’s problems started when losing Martin O’Neill. Not satisfied with the direction the club was going, O’Neill left the club, with Villa going through Gerard Houllier, Alex McLeish, Paul Lambert, Tim Sherwood and Remi Garde before being relegated in 2016.

Leeds were far too ambitious for their own good even if they lived the dream, Newcastle was a series of poor decisions and a hole created by a club legend, while Villa started with the loss of a high-quality manager who was never properly replaced.

No one will accuse Tottenham of being overly ambitious, but there are certainly similarities between their demise and that of Newcastle and Aston Villa.

Tottenham never really replaced the irreplaceable Harry Kane. Savvy clubs can sell their best player for a massive sum and rebuild adequately, as Liverpool did when selling Philippe Coutinho, building a squad that could win a Premier League and UEFA Champions League.

Tottenham, under Daniel Levy, were never that savvy. Getting £86m for a 30-year-old with a year to run on his contract was incredible business from the selling club, not that it’s done them much good, even if replacing a figure like Kane is difficult.

Interestingly, Southampton were relegated three years after losing homegrown icon Matt Le Tissier and Newcastle were relegated three years after losing the talismanic Shearer. Tottenham sold Kane three years ago…

Considering Kane’s departure, new boss Ange Postecoglou’s first season was certainly impressive, but when European football was added, the side collapsed. The departure of Son Heung-min added to their woes with Thomas Frank tasked with turning Tottenham’s fortunes around.

It’s hard to know how the Brentford boss would have fared were his side not littered with injuries, but it’s similarly hard to fathom how Tottenham have so often started with two of Rodrigo Bentancur, Pape Sarr, Joao Palhinha and Yves Bissouma in their midfield. The January addition of Conor Gallagher made that easier to understand.

Tottenham fans have spent years protesting about the running of the club and how they bring in so much money and don’t spend it. The issue is not that Tottenham couldn’t or wouldn’t sign players, it’s that they’ve spent years signing the wrong ones and they’re now teetering on the brink of relegation as a result.

Tottenham fans must be wondering how on earth it’s come to this. What was the sliding doors moment that took them from playing in a UEFA Champions League final to potentially playing in the Championship?

A good place to start is 19th November 2019.

Mauricio Pochettino turned Tottenham from nearly men to UEFA Champions League regulars and even UEFA Champions League finalists. Levy’s top priority should have been doing whatever it took to keep Pochettino at the club. Instead, he failed to back, and then opted to sack, one of Europe’s finest managers.

The summer of 2019 was an opportunity for Tottenham to kick on. Instead, they spent nearly £100m on Tanguy Ndombele, Ryan Sessegnon and Jack Clarke. Spurs started the season poorly, and Pochettino was shown the door, replacing him with Jose Mourinho in a move that might have been considered an upgrade were it made four years earlier.

It’s worth remembering that in Mourinho’s two full seasons at Manchester United, Pochettino’s Tottenham outscored United by 13 points. Levy fell for Mourinho’s allure and his apparent guarantee of trophies… only to sack him on the eve of a cup final.

Antonio Conte was in soon after, an affair that ended entirely predictably, with the fiery Italian saying "20 years there is the owner and they never won something, but why? The fault is only for the club, or for every manager that stays here?"

It was not a thinly veiled attack of Levy but a full-frontal assault, and it was hard to argue with.

Levy deserves credit for much of his running of Tottenham Hotspur; he’s turned the club in a financial giant, lining up amongst Europe’s best without the history of Bayern Munich, Real Madrid or Bayern Munich, nor the Middle East money of Manchester City or Paris Saint-Germain.

But that’s where the credit ends. Levy didn’t know how to run the football side of things and shoulders responsibility for the misdirection on that front. His departure last summer came long after the damage had been done and the rot had set in.

The appointments of Johan Lange and Robert MacKenzie have have done the club no favours either, with the duo spending £350m on Dominic Solanke, Archie Gray, Wilson Odobert, Lucas Bergvall, Antonin Kinsky, Xavi Simons, Mohammed Kudus, Mathys Tel, Kevin Danso, Luka Vuskovic, Kota Takai.

Poor choices at boardroom level, poor recruitment in the transfer market and poor managerial hires. It’s never one bad decision that brings about a crisis, but several.

Over the last few years, Tottenham have made one bad decision after another, and chickens are coming home to roost.

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