Friday marked exactly 15 years since Tottenham Hotspur last won major silverware. Their fans have turned a win in the 2019 Audi Cup into a sort of half-meme, half-coping mechanism. But in terms of the genuine article, Spurs’ 2-1 triumph over Chelsea to lift the 2008 League Cup remains their last trophy.
On Sunday, Tottenham and Chelsea meet again on the day the rebranded EFL Cup will be decided. The difference this time is that the trophy will be contested by Newcastle United and Manchester United, rather than the two London rivals.
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Chelsea have problems of their own. Despite having bought every player in world football, they sit tenth in the Premier League table. But this is a side that won the Champions League, European Super Cup and Club World Cup as recently as 2021. They’re hardly starving for success. But is it the man who lifted an FA Cup and a Premier League title with them not too long ago that stands out as they meet Spurs.
Antonio Conte was the last manager not named Pep Guardiola or Jurgen Klopp to lift the Premier League title. The success didn’t stop there. When the inevitable acrimonious split came, a touchstone of Roman Abramovich-era Chelsea, Conte returned to his home nation. He led Inter Milan to their first Scudetto in over a decade. It was his fourth as a manager, having racked up three Serie A titles with Juventus.
Conte left almost immediately after winning the league, reportedly due to a dispute with the board over transfers. This meant that when he walked through the doors of the Tottenham Hotspur Stadium, the north London club was getting a manager in his prime. Spurs has gone down the “serial winner” route before, but Jose Mourinho was ultimately too shopworn to have an impact. However, Conte was breezing in on the back of one of the finest achievements of his career.
Conte has been in situ now for around 15 months. Spurs have not exactly clicked under his stewardship. His tenure has been far from dreadful. They qualified for the Champions League last season and made it to the knockout stages this year. They trail AC Milan 1-0 after the round of 16 first leg. Their league position at present is not an improvement but is a maintaining of standards. Spurs sit fourth, though fifth-placed Newcastle do have a game in hand on them.
But Conte wasn’t hired to keep Spurs ticking over. You bring in a manager of his stature and standing to win trophies not tread water. But the closest they’ve come to ending their 15 year wait was a two-legged defeat to Sunday’s opponents Chelsea in last season’s EFL Cup semi-final. Conte will have noticed the poetic nature of the defeat, though he likely won’t have appreciated it.
The Italian has spent much of his Spurs spell with an eye on the exit door. The idea of Conte leaving has gained steam in the manager’s absence, as he recovers from gallbladder surgery. Speculation is rampant over whether the former Italy head coach will remain. He has publicly doubted whether Tottenham can match his ambitions in the past and that view doesn’t seem to have gone away.
But shouldn’t a “serial winner” be able to turn a squad with the likes of Spurs record goalscorer Harry Kane in the ranks into champions of some kind? During his tenure, Conte has led his team in competitions big and small. Is it unreasonable to think he should at least have picked up an EFL Cup or a Europa League along the way? Or that he should prioritise doing so rather than throwing his hands up?
The safe, cuddly spectre of Mauricio Pochettino remains in the corridors of the Tottenham Hotspur Stadium. ‘Poch’ got more out of this club than anyone has in decades. A Champions League final and a genuine title challenge in the year Leicester City did the unthinkable might not fill a trophy cabinet, but they have lingered in the memory. But Conte has a far more impressive CV than the Argentine. Shouldn’t he be able to at least match, if not better, what Pochettino did?
Conte won’t match Pochettino’s achievements this season. If he turns tail and runs, seeking a club more conducive to his methods or perhaps just closer to trophies than Spurs are, then he never will. But if you’re a serial winner who has stopped winning, perhaps it’s easier to blame the club than yourself.
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