Tottenham, the Europa League and an identity crisis that has ...

The last time FK Qarabag came to Tottenham was nine years ago last week. It was Mauricio Pochettino’s second season and his team had started slowly, with six points from their first five Premier League games (one fewer than they have right now). Enthusiasm for the start of their new Europa League campaign was limited, with almost 10,000 unsold seats in the old White Hart Lane. And when Qarabag went 1-0 up through an early penalty, the fans who did go might well have wondered if all this was worth it. This was Tottenham’s fifth consecutive season in the Europa League and the competition had often felt like a burden, slowing Spurs down in their pursuit of what they really wanted: Champions League football.

But in another light, that night against Qarabag turned out to be significant. Pochettino was trying out some new players he hoped would take his team to the next level. As well as a first Spurs start for Kieran Trippier, this was a second for both Son Heung-min and Dele Alli. After going 1-0 down, Son swept home an Andros Townsend corner, his first goal since arriving from Bayer Leverkusen. Two minutes later came the wonderful second: Son passed to Dele, who skipped away from a sliding defender, and returned the ball to Son, who scored.

The arrival of Son and Dele into the first team was far more important than the fact Tottenham won 3-1. They became two of Spurs’ best and most popular players of the modern era and Tottenham were excellent for the next six months, challenging Leicester City for the title and eventually going out of Europe in the last 16. But as they faltered near the end, it was impossible not to wonder whether they might have kept the pace with Leicester if they did not have those extra 10 European games.

Welcome to the dilemma of the Europa League. Spurs start their campaign against Qarabag this Thursday, their seventh in this competition since it was rebranded in 2009. (Not including 2016-17, when they dropped into it from the Champions League and were promptly knocked out by Gent.)

Ange Postecoglou will now face the same questions that Harry Redknapp, Andre Villas-Boas, Pochettino and Jose Mourinho all wrestled with before him: is this a trophy Tottenham should be pushing to win? Is this a chance to try out the young and fringe players? Above all, can a club that defines itself by being in the Champions League — ‘Top Four’s Our Everything’ FC — afford to put their eggs in this basket? Or can a club that has not won a trophy since 2008 afford not to?

Tottenham have not punched their weight in Europe’s second club competition since that rebrand 15 years ago. They have played in it enough times and generally been among the favourites, but their best run was under Villas-Boas in 2012-13 when they reached the quarter-finals and lost to FC Basel on penalties. More often than not, they have looked as if they were keener to get out of it than to win it and in doing so turned up their noses at a trophy that should not have been beyond them.

There is no reason Tottenham should not aspire to win the Europa League. Wishing you were in the Champions League instead is no excuse. Since the rebrand, Chelsea have won it twice (2013 and 2019) and Manchester United once (2017). Atletico Madrid have won it three times (2010, 2012, 2018). These are all teams you would associate with the Champions League, but when in the Europa League, they did not jealously wish they were playing on Tuesdays and Wednesdays. They tried to win on Thursdays instead.

Maybe that will change with Postecoglou. He is the first Spurs manager in years to not talk about Champions League qualification as an end in itself. (It’s not a “Willy Wonka golden ticket,” as he memorably put it last season.) He has spoken boldly about his own record of winning a trophy in his second season at a club. So why not? Why shouldn’t Postecoglou aim to take Tottenham all the way to Bilbao next May?

Tottenham’s mixed history with this competition started in 2011-12, in Redknapp’s last season at the club. This was the season after their famous run to the quarter-finals of the Champions League and Redknapp could not have made it clearer that his goal was to get back there. He played the kids, which meant some early minutes for Harry Kane and Danny Rose, as well as Tom Carroll and Iago Falque.

Quite unusually, Spurs failed to progress from their group, even with 10 points. But after defeat at home to PAOK in the penultimate game put them on the brink of elimination, Redknapp could hardly have sounded less bothered. “You can’t have it all ways,” he shrugged in his post-match press conference. “The important thing is that we have the players fresh for the Premier League at the weekend.” Spurs did in fact finish fourth in the league that season. And if Bayern Munich had beaten Chelsea in the Champions League final, then Spurs would have been back in the Champions League in 2012-13. Redknapp’s gamble almost paid off.

But when Villas-Boas replaced Redknapp in the summer of 2012, he took a very different approach. Before Spurs’ first game against Lazio — Hugo Lloris’ debut — he said in his pre-match press conference that he wanted to transform how everyone at the club saw the Europa League. “The most important thing for you is to change (the mentality) of the players so this midweek game starts being important once again,” he said. “If this was a Champions League game, most of the players would be willing and would be making sure they were completely fit.”

It was a brave policy from Villas-Boas given he was always going to be judged by whether he could finish fourth. It would have been easier to just focus on that and forget about Thursday nights. But there was something thrilling about how much he obviously cared about Europe. Especially as he kept playing Gareth Bale, in the season when he played as if unbound by traditional limits.

Of all Bale’s scarcely believable performances that year, one of the greatest was Lyon at home in the last-32 first leg. He scored a brilliant free kick at the very end of the first half and then another at the very end of the second.

When Spurs hosted Inter Milan in the last-16 first leg, they blew them away with a fast, relentless performance, winning 3-0. Days after beating Arsenal 2-1 at home, this was the high point of the Villas-Boas era. It felt at the time like they could win the Europa League and still have enough in the tank to get fourth. Of course, the reality was ultimately rather different. Spurs ran out of steam, only scraping through the second leg in Milan, then looking exhausted when they faced Basel in the quarters. Mohamed Salah ran rings around them at White Hart Lane, Bale injured his ankle, and while Spurs survived with a draw, they ended up drawing the second leg and losing on penalties. The “negative spiral” Villas-Boas had predicted of Arsenal actually belonged to Tottenham. They ended up fifth, one point behind Arsenal. Villas-Boas’ bet on Europe was a bust. He lasted only half of the following season.

So it was Tim Sherwood rather than Villas-Boas who took over for the knockout rounds the following year. Spurs had Benfica in the last 16, a tie most notable for Benfica manager Jorge Jesus taunting Sherwood when Benfica went 3-1 up at White Hart Lane. Sherwood said before the return leg that he had “no respect” for Jesus and that Tottenham had received “a lot of emails from Benfica fans apologising for their manager’s behaviour”. A second-string Spurs team drew 2-2 in Lisbon — two assists from a 20-year-old Kane — and were eliminated.

When Pochettino replaced Sherwood, there was a chance for a reset in Spurs’ relationship with the competition. It gave Pochettino a chance to look at new players who would soon enough be part of his first team. Kane was especially keen to make the most of his opportunities, burying a 20-yarder at home against Besiktas on his way to becoming first choice.

There was something slightly haphazard or even comical about Spurs’ campaign. When they travelled to Besiktas — playing in the Ataturk Stadium because Besiktas’ new stadium was under construction — the floodlights kept failing, forcing the players off the field. When Spurs hosted Asteras Tripolis, fans were treated to one of the most memorable European nights of recent years. Kane scored a hat-trick and ended up in goal after Lloris was sent off. Lamela scored a rabona (his first of two for Spurs) that no one who was there will ever forget.

But this campaign ended just like 2012-13: unpicked by Salah in the knockout rounds (this time with Fiorentina), with Spurs looking flat and exhausted. Fans might remember Roberto Soldado running through on goal with all the time and space in the world and messing up a pass to Nacer Chadli. Tottenham did not have the legs or the experience to compete in Europe and at home at the same time.

The following season — when their group stage started against Qarabag — they did at least get their revenge over Fiorentina, knocking them out at the last-32 stage. But it was a familiar story in the last 16, coming up against a stronger, sharper Borussia Dortmund and losing 5-1 on aggregate having rested several key players. The last European game at the old White Hart Lane ended in defeat and as Spurs stumbled at the end of their league season, finishing third in the end, it felt as if playing 10 games in Europe without even getting to the quarter-finals was the worst of both worlds.

Tottenham played as if they knew that their future was in the Champions League. They qualified for it the following season for the first time since 2010. Their first Champions League group stage campaign under Pochettino was a lesson in football at that level — they finished third and dropped back down to the Europa League.

Drawn against Gent in the last 32, Tottenham should have been big favourites. This was halfway through the 2016-17 season, when Spurs were at their peak, almost unstoppable, and were beating everyone they came up against. Maybe they thought they were too good for the Europa League at this point because they lost 1-0 in Belgium, with Dembele admitting afterwards that Gent “wanted it more than us, they were sharper, more motivated than us”. Spurs drew the return leg 2-2 after a Dele red card and were out of Europe again.

This was Spurs’ last involvement in the Europa League for three-and-a-half years. During that time, Pochettino took them to a Champions League final, a run that made their long Europa years feel very far away. But just over one year on from Madrid, they were back in it, managed by Jose Mourinho. You could be forgiven for memory-holing most of this campaign, which was played behind closed doors. What people will not forget is how it ended against Dinamo Zagreb. Spurs won the first leg 2-0 but looked frozen in the second leg in Croatia against a team whose manager had just been sentenced to prison. They lost 3-0 and were knocked out. Lloris said it was a “disgrace”, in what remains the most explosive post-game interview ever given by a Tottenham player. Mourinho was sacked four games later.

So is it a cursed history? Or is it just a story of an identity crisis, of a club that can never quite work out how seriously they want to take this competition? At times, Spurs’ desperation to be in the Champions League has meant they have taken their eye off the ball and in doing so missed the opportunity to win a trophy that would do more for their status — and the fans’ happiness — than merely showing up in the Champions League.

And even if Tottenham do not make it all the way to Bilbao — which is 14 or even 16 games away depending on where they finish in the initial league stage — it could be an invaluable chance to look at the Spurs players of the next generation. Qarabag could eventually mean to Lucas Bergvall and Archie Gray what it did to Dele and Son nine years ago.

(Top photos: Getty Images)

Jack Pitt-Brooke is a football journalist for The Athletic based in London. He joined in 2019 after nine years at The Independent.