Tottenham: Harry Kane, Nuno Espirito Santo & Conference League – can Spurs emerge from the confusion?

Nuno Espirito Santo took his second Spurs preseason win at League One MK Dons on July 28th

It seems much longer than a good two years since Mauricio Pochettino sat at the national stadium in Singapore and told a room full of journalists that he would have likely quit as a Tottenham coach if they had won the Champions League final six weeks earlier.

“But after the final, I didn’t think it was great to end like this,” he continued. “I’m not a person who avoids problems. I love great challenges.”

Back then, no one could have known what problems Spurs would face, nor the true extent of the challenge that lay ahead.

Nobody knew that Pochettino would be gone within four months, nor that his successor, Jose Mourinho, would follow him out the door not long after. Nobody knew a global pandemic would deliver a financial kick in the guts, so strict chairman Daniel Levy estimates it will cost Tottenham £ 200m in unrecoverable revenue.

There will be no Champions League final for Spurs this season. That their Europe campaign is taking place in the newly formed Europa Conference League is a dent in their pride, only mitigated by the knowledge that old rival Arsenal is completely missing out on.

With Nuno Espirito Santo, another new manager at the helm, it feels like a completely different club in some ways.

The Kane Confusion

It’s a measure of the change Tottenham has seen since then Champions League final loss to Liverpool that possibly only two of their starting XI in Madrid – Hugo Lloris and Son Hueng-min – will play for the Premier League opening game against champions Manchester City on August 15th.

Danny Rose and Toby Alderweireld’s departures this summer mean five players – including the entire defense – have left the club.

The irregular shape and injuries of Harry Winks, Moussa Sissoko and Dele Alli mean they have not all started the same Premier League game since December 26, 2019.

And then there is Harry Kane. It will be fascinating how the situation around the English skipper develops.

Striker Kane thinks he has a gentlemanly agreement to leave. He wants to move to Manchester City. City wants him. Tottenham denies the first piece exists, citing the three years he has left on his contract as proof the 28-year-old is not going anywhere.

Various rumors have been circulating about what will happen next, but until Kane returns to the club – or declares he won’t – and there is clarity about how he thinks about the future, the story won’t go away.

City of Tottenham’s first opponent of the new season just adds one more intrigue to a delicate situation that Levy needs to make the right decision.

Harry Kane has been with Tottenham since he was 11

Conference complication

It can be assumed that the anticipation for the play-off draw of the European Conference League on Monday is not exactly the same as for the group stage of the Champions League.

Spurs are in the competition after finishing seventh last season, their lowest level since 2009. They ended up behind West Ham United for the first time since 2008.

After beating Manchester City 2-0 in their ninth game for the Premier League leaders on November 21, Tottenham only picked up 42 points from 29 games.

If their average of 1,448 points per game over that period had spanned the entire season, they would be level with Aston Villa, who finished 11th.

Striker Lucas Moura believes Tottenham is to blame for being in Europe’s third division competition – a play-off win is still required to reach the group stage.

“It’s difficult to talk about justice in football,” Moura told BBC Sport.

“We know the Premier League is tough and if we don’t do well we won’t qualify for the Champions League or even the Europa League. It’s our fault. It’s everyone’s fault.”

“We have the quality to do better – better than last season. Let’s fight for it.”

Trophy search continues

Even if the memories of Tottenham’s chaotic search for Mourinho’s replacement are fresh, the club seems to be in focus again.

#NoToNuno may have been trending when it emerged that Spurs were focused on the Portuguese – after their attempts to lure Pochettino back down, talks with Antonio Conte and the mess over Paulo Fonseca and Gennaro Gattuso failed.

But the former Wolves boss Santo approached his task with pleasure.

“To dare is to be done,” he repeated in a chat with the club media, remembering the Spurs’ motto. “I love that. It’s what we want.”

Nuno worked hard for his players in preparation and drew parallels with the physical demands Pochettino placed on the squad. And technical director Fabio Paratici was very busy considering the amount of time he spent on the phone in public.

Spurs face Chelsea and Arsenal in their last two friendlies in preparation

Two new additions – Italian Goalkeeper Pierluigi Gollini and Spanish Winger Bryan Gil – have already arrived with the prospect of more to come.

In the early pre-season games, Nuno avoided the three-man defensive line-up that was the foundation of his success at Wolves, but when all of his internationals return and the club’s summer recruitment process is over, it will be interesting to see if he returns or calls the back four he switched to last season at Molineux with mixed results.

Gil’s signing and search for a striker – Fiorentina’s £ 40million Dusan Vlahovic has been most closely linked – suggests a fresh approach to whether or not Kane stays.

And for Moura, that justifies his belief that Tottenham’s search for a trophy – which has been mentioned every year since 2008 but always ends in disappointment – is nearing its end.

“I’m always a positive guy,” he said. “Of course there is a new philosophy or a new type of training when changing coaches. But it’s also exciting because every player wants to show something and show that they can start.

“We’re training really hard and I’m sure we’ll be ready for the season.

“My goal and the club’s goal is always to win something. It’s time for us to win a trophy.”