The title is a major provocation, but not too far from reality. Leaving aside the history of the two clubs, on one side one of the most successful and historic teams in Europe, on the other a team that has not written memorable pages, current reality brings Milan and Tottenham closer together than we would like to admit.
The facts say so, the performances say so, the constant climate of protest towards the ownership says so, the very few trophies won while opponents collect them says so, and the repeated humiliations suffered on the pitch say so. Milan, since RedBird arrived, is becoming the Tottenham of Italy, spitting with disdain on its glorious history built with great effort and pride over the years.
We leave you with three statements, fairly recent, from three very important coaches who have recently managed Spurs. We are talking about Conte, Mourinho (they need no introduction), and Postecoglou, who won the club’s only trophy in the last 17 years.
For instance, even broader discussions around the modern game, such as analyzing World Cup 2026 outright markets, reflect how football today is increasingly driven by long-term planning, expectations, and the pressure to consistently compete at the highest level.
Milan and Tottenham: uncomfortable structural similarities:
Let us start with Antonio Conte, who erupted in a press conference after a 3–3 comeback draw: "I think now it is much better to go into the problem, because the problem is that we have shown we are not a team. They are used to it here, they do not play for anything important. They do not want to play under pressure, under stress. The history of Tottenham is this. 20 years with this owner and they have never won anything. Why? Is it only the club’s fault or the coaches’? I have seen the coaches who have been here… So far I have tried to hide the situation, but now enough. Because I do not want to see what happened today anymore, because it is unacceptable. Also out of respect for the fans, who follow us and pay for a ticket."
We then move on to José Mourinho, who before the Europa League final between Roma and Sevilla admitted, answering a specific question in a press conference: "The only club in my career for which I no longer have deep feelings is Tottenham. Probably because Mr Levy did not allow me to play a final and win a trophy. It is the only club."
And finally we come to Ange Postecoglou, dismissed after winning the Europa League against Manchester United. The Australian-born coach spoke a few weeks ago about Spurs without filters: "Tottenham as a club used to say ‘we are among the big ones’, and the reality is that, according to my experience over the last two years, they are not. When Arsenal need players, they spend £100 million on Declan Rice. I do not see Tottenham ever doing something like that. When you enter Tottenham, what you see everywhere is ‘Audere est Facere’, ‘to dare is to do’. It is everywhere. And yet their actions are almost the opposite of this, right? You have to give credit to Daniel Levy (the club chairman, note) because that path led to a new stadium and new facilities, taking a safe route. I think they did not realise that, to truly win, at some point you have to take risks. It is really curious to understand what they are trying to build. What are they? Obviously they have built an incredible stadium, incredible training facilities. But when you look at spending, particularly the wage structure, they are not a big club."
Apologies for the length, but these are statements of incredible force. When have we ever heard words like this in the world of football, an environment always very muffled and never inclined to “real” controversy, the kind that touches on important truths that everyone knows and nobody says? Three top-level coaches, and all three in agreement about the club’s many problems. The most important one: there is no intention to win. There is not even an intention to try to win. They just muddle along, relying on the stadium and the huge Premier League revenues. It is not hard to believe, half seriously and half jokingly, that if people on the fourth floor of Casa Milan read the title of this piece they would exclaim: “If only, at least we would have a stadium!”
Let us return to the argument in order. The common points are becoming worrying. A club that claims ambition only in words but every year does not really compete for anything. Tick. Tight wage bill compared to rivals. Tick. Players lost on the transfer market for a few hundred thousand euros (Eze to Arsenal, Thuram to Inter). Tick. A centralising figure who interferes in all areas of the club. At Tottenham until last year there was the executive chairman Daniel Levy (who left the club after 24 years in the role) and at Milan there is CEO Giorgio Furlani. Tick again. In London, fans and coaches have complained openly about Levy. In Italy there is unprecedented protest, with petitions and stadium demonstrations, against CEO Furlani, accused of overstepping his role and effectively turning Milan into his personal “playground”. It is now out in the open: in January the Mateta case caused embarrassment when Tare was overridden by the CEO. Something similar had happened years ago, when Maldini was still there, when Dybala’s agent was contacted.
Milan, extreme attention is needed...
It is very easy to slip into the abyss without realising what has happened: Tottenham went from playing Champions League and Europa League finals to fighting relegation for two consecutive seasons. And this year it is not even certain they will stay in the Premier League, as pointed out via those at Milan News.
Be extremely careful, do not play with fire. With this mentality and this gradual acceptance of repeated sporting humiliation, almost becoming anaesthetised to mediocrity, it is very easy to end up in tragic situations, sportingly speaking. There is a vital need to restore sporting dignity to Milan, which unlike Tottenham, as history shows, has had it in abundance.
