From a shambles at Chelsea to a mess in Milan: Christian Pulisic is swapping one crisis club for another

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The American's career certainly wasn't helped by the circus at Stamford Bridge, but there is a lot of uncertainty swirling around San Siro right now

Christian Pulisic clearly needed to leave Chelsea this summer. His career had stagnated at Stamford Bridge. He played under three different managers last season: Thomas Tuchel, Graham Potter and Frank Lampard. Not one of them considered Pulisic worthy of a regular starting spot.

Pulisic was obviously hindered by injury issues - again - while the chaos caused by the new owners' spending spree hardly helped matters. He was pushed down the pecking order by inferior players. It is, therefore, easy to understand why he jumped at the chance to move to AC Milan. If he remains fit, regular game time is guaranteed.

However, is he simply swapping one poorly-run club for another? Chelsea's new owners appear to have more money than sense, but they certainly don't lack ambition. They clearly want to win. But can we really say the same about their fellow Americans at San Siro?

Pulisic has done well to escape from the circus at Stamford Bridge, but there is a legitimate fear that he is walking right into the middle of a mess in Milan.

  1. Maldini's masterpiece ruined?

    Maldini's masterpiece ruined?

    Paolo Maldini called AC Milan's 2021-22 Serie A title triumph "a masterpiece" - and it was. He had been technical director for three years and acquired 21 players at a net cost of €75 million (£64m/$82m) - as much as Juve had paid for a single signing, Dusan Vlahovic, midway through the season.

    In that sense, Milan's Scudetto success felt more like a minor miracle. Nobody had expected them to challenge for the title that season - let alone win it. “It is a victory of ideas, of hunger, of team spirit," Maldini told the Gazzetta dello Sport in May 2022. "We were up there for two years, completely against all predictions. That's what made us so proud."

    But Maldini was also fearful. He knew full well that Milan had overachieved, that sustained success at the highest level is impossible in the money-saturated modern era without serious and continual investment in the squad. And he wasn't shy about saying it.

    “What we need now is the club wanting to open up a new era," he said. "With a strategic vision, Milan could next season compete with the biggest clubs. However, if we were to choose a vision of maintaining our current level, without investment, without an idea worthy of Milan, we would remain in limbo among the top six or seven sides in Italy, hoping to maybe win the Scudetto again and qualify for the Champions League.

    "This is the moment that the owners, Elliott or whoever could arrive, need to realise this three-year project is complete and figure out what strategy they want for the future. With two or three important signings, and the consolidation of the players we have, we can compete for something bigger in the Champions League."

    And last season they did, sensationally reaching the semi-finals for the first time since lifting the trophy in 2007. But, in truth, Milan had no business being there.

  2. 'Risk taking two steps back'

    'Risk taking two steps back'

    Their struggles in Serie A gave a far more accurate reflection of the strength of Stefano Pioli's side - they only finished fourth because of Juve's points deduction - and their lack of depth was eventually exposed by Inter, who swept Milan aside in the derby of derbies.

    Maldini wasn't the least bit surprised either. "As we said last season, we are not yet built to handle two tournaments," he told Mediaset. "We said that to the media, but also to the club owners, so they know that full well.

    "This journey started four years ago, which took great results, both economic and sporting, built a young foundation to the squad and there are roughly three years difference in the average age of our squad to Inter’s, and that lack of experience tells at this level.

    "You are never sated at Milan, that is not allowed. I think there are opportunities to take, so reaching the Champions League semi-final is something we must make the most of economically too."

    Maldini was adamant that the money made from their European run simply had to be pumped back into the squad. If it wasn't, Maldini told Amazon Prime Italia, "Milan would risk taking two steps back." By that stage, it was clear that Maldini had very different views on how to run a football club to Gerry Cardinale, the founder of RedBird Capital Partners, who acquired Milan from Elliott last summer. The American has made no secret of the fact that he was "educated" by Billy Beane, the man behind the 'Moneyball' approach to player recruitment that revolutionised baseball.

    "Billy's been in European football for 20 years and he told me I wasn’t looking at the situation in the right way," Cardinale revealed during a seminar at Michigan Institute of Technology in March. "I had to approach European football with the ‘Moneyball’ mentality, which says there is no need to sacrifice the level of performance on the field for cash flow or vice versa."

    Maldini fundamentally disagreed with that view, making a parting of the ways inevitable.

  3. 'Sacking will never erase Maldini's history'
    Getty Images

    'Sacking will never erase Maldini's history'

    Still, when the end came, it was shockingly abrupt. According to La Repubblica, showdown talks between Maldini, sporting director Ricky Massara and Cardinal lasted just 35 minutes. Maldini and Massara's exits were confirmed just a couple of days later, with cold, succinct statements.

    Indeed, when Milan's social media channels acknowledged Maldini's birthday later that month, it sparked an unsurprising pile-on, with fans lashing out at the club for having the audacity to send their best wishes to a club icon that they believed had been treated with gross disrespect. Even Milan's ultras were irked by the way in which Maldini had been treated, which was significant given they had had an issue with the former captain dating back to his playing days.

    "Regarding the events of the last few days, we would like to sincerely thank Paolo for the work he has done over the years,” the Curva Sud said in a statement. "Making up the relationship that was interrupted on the day of the farewell to football was certainly the most beautiful passage of the path lived together in recent seasons, which brought Milan back to winning in Italy and to be competitive in Europe.

    "And a large part of these results must certainly be ascribed to Paolo and to the tireless work done, always distinguished by the love for our colours. A sacking will never erase Paolo Maldini’s history with the Rossoneri, a great captain on the pitch and an example of Milanism for all of us. This must be the only objective of the owners and of those who will take care of the technical area from today, to build a strong team capable of fighting on all fronts."

    The question now is whether Cardinale & Co. are capable of fulfilling that objective - or whether it is even one that they share.

  4. 'We don't need Maldini'
    AC Milan

    'We don't need Maldini'

    When former Italy boss Cesare Prandelli was asked about Maldini's exit, he told the Gazzetta, "We have to understand what these people from investment funds want. They want to make money."

    Maldini would obviously agree. He clearly felt the owners were more concerned with generating profits than lifting trophies. Essentially prophesying his own exit, Maldini stated back in May 2022, "I am not the right person if you want to build a project that isn’t aimed at winning. I could never do that."

    Milan haven't even attempted to hide the fact that there was a clash of ideologies, with president Paolo Scaroni effectively suggesting that Maldini's role had become redundant, that his pulling power - so crucial in attracting players to San Siro during a difficult time for the club - was no longer required.

    "It is very true that Maldini had a certain impact in negotiations and to this day I are very grateful to him, but I must also say that nowadays - and I hope it doesn’t seem ungrateful - we don’t need him as much," Scaroni told the Corriere della Sera last month. "At the time, Milan were just coming out of the Yonghong Li era and struggled to attract talents. Milan today won the Scudetto and reached the Champions League semi-finals, so I think the club in general is more attractive."

    However, even Scaroni acknowledged that several star players had been left bitterly upset by Maldini's dismissal. The likes of Mike Maignan, Theo Hernandez and Rafael Leao had all publicly acknowledged that the former technical director had been crucial to convincing them to move to Milan.

    It is also telling that Franco Baresi, Maldini's former team-mate and fellow club legend, will be a more visible presence at Milan next season. He will continue to carry out an ambassadorial role, but is expected to do more interviews before and after games - a seemingly tacit attempt to keep the fans onside by showing that the club hasn't lost all connection with its roots.

  5. Milan now a selling club?
    Getty Images

    Milan now a selling club?

    Doubts persist, though, and they will only be removed by statement summer signings because, after Sandro Tonali's transfer to Newcastle United, there is very real concern among the supporters that Milan have become a selling club - and that the owners have no issue with such a status. Or worse, see it is a perfectly acceptable business model for a football club.

    Cardinale would obviously argue that when he gave Maldini €32m (£27m/$35m) to spend on one player last summer, it was completely wasted on Charles De Ketelaere, one of the biggest flops of the season - and not only in Serie A, but all of Europe.

    Maldini's counter-argument would be, though, that if you're only going to invest in young players, then you need to be patient with them, and give them time to settle, and then grow. As he said all along, sometimes you need proven winners to play alongside relative novices to take a team to the next level, and he wasn't alone in that regard.

    Ahead of the final game of last season, the fans unfurled a banner at San Siro that read, "Another year has passed, it is time for the transfer market. We want [to take] a step up the ladder."

    Pulisic can certainly help in that regard. His transfer certainly isn't being viewed as a 'Moneyball' move - not least because his numbers last season were atrocious. It's considered a positive development in Milan simply because it's clear that there is a top player in there trying to get out; one that has been held back by injuries and his own inconsistency over the past few years.

    He's also capable of playing in a variety of positions, so he's entirely in keeping with Pioli's fondness for multi-purpose players. Given Milan's abysmal alternatives, he will probably be deployed on the right wing, but there's also a strong possibility he will be asked to play as a No.10, particularly with Brahim Diaz gone back to Madrid.

    Other voids will be far more difficult to fill, though.

  6. Prudence or parsimony?

    Prudence or parsimony?

    As it stands, Milan's midfield is threadbare, to put it mildly. Only Ruben Loftus-Cheek (another Chelsea reserve) has arrived thus far to strengthen a department decimated by Tonali's sale and a serious injury to Ismael Bennacer, who might not return this year.

    The idea is to bring in Tijjani Reijnders, but there is a growing concern that Milan might not be willing or able to meet AZ's asking price of €25m (£21m/$27m) - and the same goes for their primary target in attack, Alvaro Morata, with Atletico Madrid demanding just over €20m for the Spain international. The fact that Milan are said to be now exploring cheaper alternatives tells you everything you need to know about the owners' approach to the transfer market.

    In this era of excess, sensibility and sustainability are values that should be lauded. Nobody is advocating a Chelsea-like recklessness in the transfer market either - it was that kind of foolishness that left Milan on the verge of bankruptcy in the first place.

    Maldini helped clean up the mess made by the club's former Chinese owners by making one shrewd signing after another, but even he was at pains to point out that there is a fine line between prudence and parsimony, and that in modern football, you will eventually be punished for the latter. A team can only over-achieve for so long, particularly in the age of state-sponsored super-clubs.

    Pulisic, then, is hopefully well aware of what he is getting himself into. His desire to move to San Siro is wholly understandable - after all, who wouldn't want to perform at the Scala of calcio? And Milan still rank among the biggest clubs in world football.

    The key question, though, is whether they're still being run like one - and we should have our answer long before the close of the current transfer window.