Why Tottenham and trophies have never gone together – and why Ange Postecoglou must snap that streak

Tottenham’s trophy drought is, for anyone who hasn’t been paying attention, 17 years old.

More than 6,000 days have passed since Jonathan Woodgate’s header against Chelsea at Wembley Stadium, back when people still thought Carabao was some kind of reindeer.

But the great trophy-laden era for Spurs, two decades of serious league silverware, the 1961 FA Cup Double and a song about cup glory at White Hart Lane, ended with UEFA Cup victory in 1984.

Four full decades since then have produced one FA Cup and two League Cups. Fewer major trophies than Everton and Leicester City.

“It’s in black and white,” Mauricio Pochettino would say when quizzed about winning something that shows five strong years, finishing runners-up in the Premier League and Champions League.

The idea that Tottenham and trophies should go together is a misnomer.

Yes, a big club with a huge fanbase, a fantastic stadium and a beautiful training ground, but while they won those three pots in 40 years, Manchester United won 31, Chelsea 21, Liverpool 19, Manchester City 18 and Arsenal 17. That is without messing around with Community Shields, Super Cups, etc.

Spurs are lucky that anyone still considers English football a Big Six and not a Big Five.

The desperation to compete with the elite drove them through Jose Mourinho and Antonio Conte and a handbrake to Ange Postecoglou, fearing they lost something dear along the way.

It goes to the heart of Tottenham’s great mystery. What’s most important? Trophies or entertainment? Danny Blanchflower’s classic quote no longer appears in the build-up to kick-off, but followers of a certain vintage know that well.

“The big misconception is that the game is first and last about winning,” said Blanchflower, captain of the ’61 doubles winners. ‘It’s nothing of the sort. The game is about glory. It’s about doing things in style, with a touch of flair, about going out and beating others, not waiting for them to die of boredom.’

Although it was not possible to win trophies in a pragmatic way under Mourinho and Conte, everyone agreed that there had to be nicer ways to win nothing.

Under Postecoglou, they have regained a sense of adventure and restored their identity. At their best they are delighted, even though they have sunk from their winter doldrums closer to the bottom three than the top four of the Premier League and in the grip of an injury crisis and a poor run of results, reasons for cheering are hard to come by find.

Protest songs aimed at Daniel Levy are back in fashion and when the chairman is under fire, the manager is a little less confident, held hostage to the promise that he will always win something in his second season.

So they could do with tangible success in one of the knockout competitions to ease the pressure and restore some confidence in the plan as they go into this semi-final against Liverpool, the Premier League leaders, Carabao Cup holders and a team that scored six when they ended up in N17 last month. As my colleague Sami Mokbel reported last month, this semi-final is seen as crucial for the future of Postecoglou.

His ranks were depleted when Liverpool last visited and are not much better off now.

There is £12.5m goalkeeper Antonin Kinsky, who is 21 from Slavia Prague and was able to move in straight away after his work permit arrived on Tuesday. Rodrigo Bentancur returns from suspension. Radu Dragusin and Archie Gray, who played against Newcastle through illness on Saturday, are feeling stronger and 17-year-old flying winger Mikey Moore is back in contention after contracting a virus.

However, with James Maddison and Pape Matar Sarr both suspended, there could be as many as ten missing.

These are testing times for Postecoglou. His tense and irritable behavior after the match does him no favors, but those who think he hasn’t tried other things because his main message is that he won’t change his attacking policy are not looking closely.

His full backs have been kept in check to meet the emergency in central defence. With Dragusin and Gray ill against Newcastle on Saturday, he adapted his usual 4-3-3 shape to provide more protection with two deep midfielders in a 4-2. -3-1 formation.

It cost Maddison his place in the team and ultimately didn’t work as they lost again. That is seven defeats in fourteen games. Another bold decision against Newcastle was dropping Son Heung-min, and that was probably with this draw against Liverpool in mind.

Son has not been at his best this season, playing more minutes than Postecoglou would have liked due to the absences of Richarlison, Wilson Odobert and Moore, and the poor form of Timo Werner.

Son looked flat in the 2-2 draw against Wolves in the final match of last year, missing a penalty before being taken off after just over an hour.

Postecoglou has given him a breather, a rare flawless week without a match, followed by half an hour from the bench against Newcastle, hoping he will shine against Liverpool because he knows he will be needed.

Arne Slot, who Tottenham came so close to appointing in place of Postecoglou, has built the best squad in the country and anyone looking for ways to trouble them will start by looking at the space behind their full backs, especially behind Trent Alexander-Arnold when he plays.

Slot hinted at selecting a strong team at Spurs, defended Alexander-Arnold against criticism after Sunday’s draw against Manchester United and shifted towards Ruben Amorim’s tactics.

‘We always try to find arguments,’ says Slot. ‘Nine times out of ten the best argument is the quality of the team you are dealing with or their game plan.

‘United had a very good game plan: no build-up, just bring the ball long and don’t give us the chance to press them high and go to a low block, which makes it difficult for any team to create chances, which we have done properly. a lot actually.’

Spurs need Son’s sack, and he will go into the semi-final feeling refreshed and perhaps more rested after the clause was activated to extend his contract until next year. “It’s great to extend his stay,” Postecoglou said. ‘And the aim is to ensure that he finishes his career at Tottenham successfully.’

Back to that. Trophies. A tall order, but Tottenham have beaten Manchester City and Manchester United to get this far, so why not Liverpool? Why not dream of Wembley?

It would relieve pressure on the Postecoglou project.

Juande Ramos and George Graham, the last managers to trouble Spurs’ trophy cabinet, might say this doesn’t guarantee much anymore. Mourinho was sacked less than a week before the Carabao Cup final four years ago.

Ryan Mason had to lead them through the defeat to Manchester City, so the competition is not and never can be the ultimate target. Levy did not mention that he had won the award in 2008 when he was recently asked at a fans forum about his fondest memories of two decades as chairman.

He spent a billion on the stadium to host Champions League football, but for Postecoglou, stopping the clock on the trophy-less years is an essential development.