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Conceição’s AC Milan: Chaos, Conflict, and a Glimmer of Hope After Derby & Deadline Day

An impressive derby display and a busy deadline day show that there is light at the end of the tunnel for Sergio Conceicao and Milan amidst a chaotic season.

The Rossoneri have endured a season plagued by inconsistency, off-field drama, and fan unrest, but their performance against Inter and a flurry of last-minute transfer activity hint at a potential turning point. As Conceição looks to steady the ship after a turbulent start to his tenure, Milan’s latest showing on the pitch—and their moves in the transfer market—could provide the foundation for a much-needed resurgence.

A Chaotic Start for Conceicao

AC Milan entered Sunday’s Derby della Madonnina under a cloud of poor results, a fanbase in revolt and all-around chaos both on and off the pitch. There had been an initial wave of excitement that followed Sergio Conceicao’s appointment at the turn of the year, crowned by dramatic comeback victories in his inaugural matches against rivals Juventus and Inter to lift the Supercoppa. Back in the dressing room, right after Tammy Abraham’s stoppage time winner in Riyadh, Conceicao was filmed celebrating in his trademark way, cigar in mouth, dancing along to the adulation of his new players.

Less than three weeks later, however, the mood had already shifted considerably from that of the honeymoon in the Arabian night that felt like a new dawn. Back in Milan, a city the Portuguese coach knows well from his playing days at Inter, the reality of his uphill task as Paulo Fonseca’s replacement would soon be laid bare.

His first league game was a dispiriting 1-1 draw at home to lowly Cagliari, while subsequent defeats on the road to Juventus (2-0) and Dinamo Zagreb (2-1) would further take the gloss off the new boss’s sparkling start to life with the Rossoneri. His assimilation into the role of ringmaster in the circus that has been AC Milan’s season was compounded by an unedifying moment in the immediate aftermath of another late come-from-behind win—this time against struggling Parma.

Conceicao and the man he deposed as club captain, Davide Calabria, had to be physically separated from each other on the field right after the full-time whistle. The heated altercation even prompted Zlatan Ibrahimovic, in his role as a director, to descend to the changing rooms post-match and act as a peacemaker to ease the tensions.

In Calabria’s case, this unsavoury incident would prove his last action in a Milan shirt, having spent his entire career at the club and making 272 appearances in the process. Having had his armband transferred to ‘keeper Mike Maignan and his right-back berth occupied by the arrival of Kyle Walker, his rossonero jersey would soon be swapped for the rossoblu of Bologna, where he has been shipped out on loan to see out the remaining six months of his Milan contract.

Calabria, captured in tears upon his final departure from the training ground at Milanello, would be followed out the exit door by fellow member of the 2022 Scudetto-winning side, Ismael Bennacer, who left for Marseille on deadline day (only 24 hours after starting at the base of midfield in the derby).

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The Deadweight & Reinforcements

The Conceicao cull was in full swing this January with Alvaro Morata, who only joined from Atletico Madrid in the summer, also sent packing to Galatasaray to make space for the €40 million signing of Santiago Gimenez from Feyenoord (where he will return, as it happens, in less than two weeks’ time when Milan travel to Rotterdam for the Champions League play-off round).

Morata, unlike the soon-to-be departed Bennacer, was left out of Sunday’s matchday squad, with Tammy Abraham leading the line and hoping to conjure his Supercoppa heroics. Adding to the swirling chaos that comprised Milan’s derby preparations was the fact that, following Matteo Gabbia’s injury sustained during Wednesday’s defeat in Zagreb, the Rossoneri entered the game with only two fit centre halves.

One of whom, Fikayo Tomori, the club was ready to sell before he turned down a move to Spurs late on Friday, while the other—Strahinja Pavlovic—had been placed on the market at the start of the month despite only arriving from RB Salzburg at the start of the season. The readiness to dispose of the likes of Morata, Pavlovic and Emerson Royal (who was on the way to Galatasaray before he suffered an injury against Girona, kyboshing the deal), all of whom had arrived in the summer, is emblematic of the lack of any effective long-term strategy and sporting direction being implemented from the club’s hierarchy.

It also lends a degree of sympathy to Paulo Fonseca, who was fired after only six months in the job, having been given little chance to truly succeed, while simultaneously highlighting the mess that Sergio Conceicao is being asked to clean up.

Transfer Turmoil and Fan Unrest

The absence of any coherent planning and supposed sporting ambition is not lost on the fans who, since the end of last season, have been extremely vociferous in their dissatisfaction with the ownership. The final three home games of last season saw silent protests from the ultras and derogatory banners strewn across the Curva Sud, directed at the off-field management. Furthermore, the club abandoned their pursuit of Julen Lopetegui as the favoured candidate to replace the outgoing Stefano Pioli after online ridicule and a ‘No-petegui’ petition that inspired them to appoint Paulo Fonseca instead—a markedly different coach in terms of style, philosophy and personality from the Spaniard.

If it were required, this would emphasise the reasons behind the supporter’s discontent with the decision-makers in the boardroom, which has only grown more hostile as this campaign has progressed. The most prominent additions to the ultras’ hymn sheet this season have been chants directed at CEO of Red Bird Capital (Milan’s majority shareholders), Gerry Cardinale, declaring, “Cardinale Devi Vendere, Vattene!” (“Cardinale You Have to Sell, Go Away!”), or else the increasingly defiant, “Noi Non Siamo Americani!” (“We are not Americans!”).

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These protests continued into the derby, with no flags or banners on display in the Curva Sud, nor the usual pre-match spectacle of multi-tiered choreographies on show at either end of the stadium. This was in part, however, also down to the ongoing police investigation into the influence of both Milan and Inter’s organised fan groups on issues like ticketing, parking and other murky financial dealings.

The spectacle was confined to the field, where a tense first half saw the Rossoneri go into the break in front thanks to a goal from Tijiani Reijnders—the standout performer in a subpar team this season.

Milan was on course for an unexpected victory, even if it would have been their third in a row this season against their city rivals. Matteo Gabbia’s late headed winner in the reverse fixture back in September ended a run of six consecutive derby defeats for il Diavolo—a run that comprised a Supercoppa final, two legs of a Champions League semi-final, a 5-1 humiliation in September 2023 and the ignominy of seeing Inter seal the Scudetto in Milan’s ‘home’ derby last April.

The spectre of Inter’s superiority had haunted Stefano Pioli’s final two years in charge and added to the reasons for his dismissal as well as his growing unpopularity amongst supporters for whom he had ended an 11-year wait for a Scudetto in 2022.

Fonseca’s triumph got the monkey off Milan’s back and may have saved his job, albeit temporarily. Conceicao, then, ingratiated himself with the Rossoneri by turning around a two-goal deficit to win the Supercoppa before celebrating in style and had the chance on Sunday to become only the second manager in the club’s history to win his first two games against Inter (after Max Allegri). It would have been an incredible feat, not simply within the internal derby narrative but given the broader context of Milan’s season and the fact that they have only won two league games against Serie A’s current top 12 (the aforementioned derby along with a 1-0 home victory against Udinese in October).

Add to that Inter’s monstrous run of form since Matteo Gabbia consigned them to their only defeat on Italian soil this season, a third successive Milan triumph seemed exceedingly unlikely. In fact, Inter had won 20 of their 24 matches in between the two league meetings with Milan, including every away Serie A match (before the nominatively ‘away’ derby in a predominantly red-and-black San Siro) with the only blemishes on their record being home draws to Juventus, Bologna and leaders Napoli along with a 1-0 defeat at the hands of Bayer Leverkusen.

Heading into stoppage time at the Stadio Guiseppe Meazza, it seemed as though an improbable third successive derby triumph for the Rossoneri was about to come to pass until Stefan de Vrij levelled the score in the 93rd minute after an inventive chested assist from Nicola Zalewski—who had only arrived on loan from Roma the previous evening.

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It was a deserved equaliser for the Nerazzurri, in truth, having hit the post three times in the game, dominating possession and having a triplet of goals disallowed (rightly) for a combination of offsides and fouls. Inter boss Simeone Inzaghi also angrily lamented a decision not to award his side a penalty for a supposed foul on Marcus Thuram in the second half, while even Sergio Conceicao admitted that, despite the pain of a late equaliser, a draw was a fair result.

There were undoubtedly positives for the ex-Porto coach to take from the game as his side showed a doggedness and resilience that have been absent on far too many occasions this season. Another ‘useful result,’ to borrow the Italian expression, against a team that has caused Milan such painful problems over recent years bodes well considering there remains the live possibility of four more Derby della Madonnina before the campaign is out (between the Champions League and the Coppa Italia).

Kyle Walker, meanwhile, impressed on his marquee debut outing—offering hope that a solution may have been found in a longstanding problem area for il Diavolo (and at the very least meaning that Milan tifosi will be spared the horror of watching Emerson Royal start on a weekly basis). As mentioned, Tijiani Reijnders scored again, making it eleven goals this season (from an xG of 5.99 according to FotMob) as he continues to cement himself as Milan’s key man and one of Serie A’s standout midfielders.

Signs of Progress & a Promising Deadline Day

Derby day was neatly followed by deadline day and Conceicao will have been given plenty of cause for optimism to add to Sunday’s credible performance as the higher-ups finally began to show some of the sporting ambition the fans have been crying out for.

The signing of Santiago Gimenez was confirmed and a surprise loan deal for Joao Felix was secured out of the blue, suddenly handing the Rossoneri a very potent-looking frontline to attack the latter half of the campaign.

Deals were also completed for Monza midfielder Warren Bondo and Riccardo Sottil of Fiorentina to bolster the squad’s options as they fight to get back into the Champions League places. Now that Conceicao has his feet firmly in the door at San Siro, after only a month in charge that will have felt like a year, we will see whether he is able to fight through the flames that have engulfed il Diavolo for far too long.

Was his signature cigar celebration on his very own inauguration day a sign of things to come, or just like for his predecessors, are things destined to go up in smoke?

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