Why don’t Tottenham win trophies?

LONDON — The days are getting longer, and as February turns into March another clear sign of spring sprouts up through the mud: the annual discussion of whether this will be the year Tottenham Hotspur end their trophy drought, and whether trophies alone are the best measure of success for a modern football club anyway.

Tottenham head up to Sheffield United on Wednesday evening knowing that a win will put them in the FA Cup quarter-finals for the first time in five years. Win that game and they will be back at Wembley for the semi-final in April.

And people will start to wonder whether, maybe despite the dismal first halves, despite Antonio Conte’s expiring contract, despite his absence for much of February, this will be the season that Tottenham ends the pain and actually win something.

But until that day comes, this will be the question Tottenham are eternally asked.

And if they lose to Sheffield United or fail to overturn the deficit against AC Milan next week, then this will be chalked up as yet another trophyless season (last Friday marked 15 years since Spurs last won anything: the League Cup in 2008).

We will all have to wait until next spring to see if we will get a different answer.

There is a section of Spurs fans — and not a small one either — for whom the failure to win trophies is a damning failure on the part of owners ENIC.

For them, it makes up the entire case against ENIC and Daniel Levy without the need for recourse to anything else. If you walked past the anti-ENIC protest outside the stadium on Feb 5, before the Manchester City game, you would have seen one banner hanging from a fence simply saying, ‘LONGEST TROPHY DROUGHT IN 71 YEARS’.

Another banner centres on a gravestone, which reads ‘DANIEL LEVY ENIC’ at the top, and then ‘1 Trophy’ underneath. It ends with ‘DIDN’T LISTEN TO THE FANS’, which is both an unusual thing to put on a gravestone, and a strange analysis of the decisions that Levy has taken over the last few seasons.

But the verdict is clear: to have owned and run for Tottenham for more than 20 years, and to have only one trophy to show for it, is something that should be held against Levy and ENIC.

To many people, this is a distasteful banner and an unfair judgement, but there is clearly a group of fans, both match-going and online, who feel this way about the ownership of the club. (The comments section of this article will make this clear too.)

There is at least a very simple logic to what you might call the trophy-based critique of the ENIC years. Because trophies are the simplest marker of success in football. Competitions are what give competitive football its structure. And the goal of any competition is to win it. We are not operating at an advanced level of analysis here.

Tottenham start every season in three domestic competitions, and tend to be in Europe every year too. And yet despite all these competitive opportunities they have had in the 22 years of ENIC, only once have they had that magical moment of Spurs hands touching silverware. And that was just over 15 years ago when Juande Ramos’ Spurs beat Chelsea 2-1 to win the League Cup. (Only one Spurs player from that day is still playing: Tom Huddlestone of Manchester United Under-21s.)

Since then, nothing at all. Spurs are now halfway to the 30-year gap they suffered between winning the 1921 FA Cup and the First Division in 1951. And that was a very different time: Spurs only played two seasons in the top flight in the 1930s, none at all in the 1940s, and of course there was no league football at all for six years because of World War II.

But what makes this era so frustrating for many fans is that Spurs have not spent the last 15 years languishing in the second tier. We are living through a time of financial stratification and Tottenham find themselves stratified quite near the top. They have been in the top flight since 1978.

They have been in Europe for 16 of the last 17 seasons. Since the season when they won the 2008 League Cup, their worst league finish is eighth (in 2008-09). Top four always used to be the holy grail and they have finished there seven of the last 14 years.

There are plenty of teams who are shut out from competing for the biggest trophies, but ENIC’s Tottenham should not be one of them.

And yet, take a look at the teams who have won trophies in the last 15 years and many of them are teams who are far less well set up to win than Spurs.

Since this particular drought started, the League Cup has been won by Birmingham City and Swansea City, while Portsmouth, Wigan Athletic and Leicester City have also won the FA Cup. And of course, Leicester also won the Premier League in 2015-16. There is always an element of randomness in dictating who wins what.

Obviously, the teams who have won the most trophies — Manchester City, Chelsea, Liverpool and Manchester United — have far more money than Tottenham. And if you were launching a defence of ENIC, you would point to the fact that they have stayed competitive with those sides for the last 20 years despite not having the benefactors of City or Chelsea or the commercial weight of Manchester United or Liverpool. (We have been through these arguments enough times elsewhere.)

But even though Spurs have not been dominant enough to guarantee success, they have been good enough to go close.

Close enough to launch two plausible Premier League campaigns under Mauricio Pochettino, to lose a Champions League final and a League Cup final under the same manager.

They lost a League Cup final, too, under Ryan Mason in 2021, as well as another under Harry Redknapp on penalties the year after they won the competition. And in the FA Cup, they lost two semi-finals under Redknapp and two under Pochettino.

In part, it comes down to luck. So many of these big games are decided by fine details. What if Sadio Mane had not kicked the ball onto Moussa Sissoko’s out-stretched arm?

What if Michel Vorm had kept out Ander Herrera’s winner at Wembley? What if Spurs had made the most of their dominance against Chelsea the previous year? What if Spurs had held on to beat Arsenal at the old White Hart Lane in March 2016, finally gone top and put pressure back on Leicester City?

We could do this all day, but the point is that Spurs have been good enough to be denied by variance, moments, little contingent details. They have not been far away during this 15-year drought.

You might say that it comes down to ‘mentality’, although that feels like the wrong word.

If Tottenham did not have a ‘winning mentality’ under Pochettino, why did they win more Premier League games under his management than under any other manager before or since? And if Jose Mourinho and Conte brought such a ‘winning mentality’ to the club since coming in, why haven’t Spurs won more?

Perhaps the right way of looking at it comes down to priorities.

It has felt ever since the 2008 League Cup win that the priority of the club was to get into the Champions League.

That is why it mattered so much when they beat Manchester City to fourth place in 2010, and why, two years later, it was so painful missing out as Chelsea won the final in Munich and pinched their place in the competition.

When Pochettino was manager he was unfailingly on-message about this, explaining how the domestic cups were not as important as the Premier League and Champions League, and how winning a trophy for the sake of it was not his goal. (Even some fans who still adore Pochettino feel frustrated by this and wish he had invested more in the FA Cup and League Cup.)

This mood has survived after Pochettino too. Mourinho took Spurs to the League Cup final in 2021 but Levy still sacked him at the start of that week because he thought Mason would give Spurs a better chance of finishing fourth.

Mourinho has spoken since about how strange he finds it that he was not given the chance to lead Spurs out at Wembley.

But with Spurs now a semi-regular Champions League participant, and with the trophy drought continuing, might the mood be changing? If Conte guides Spurs to fourth at the end of this season it will be a success, but if he can win them something he could ensure a legacy different from any of his predecessors.

This article originally appeared in The Athletic.