A Trophy in the Desert, a Watchmaker for Nothing

Four Days in Riyadh

Four days: that was the interval Milan allowed Sérgio Conceição between the handshake and the examination. Paulo Fonseca had taken charge of his last match on 29 December; from the 30th the bench belonged to Conceição, a man of flint and vinegar; and on 3 January the Supercoppa Italiana semi-final would set Juventus in front of him, under the sodium glare of Riyadh, where modern football has taken to holding its January feasts. Audition, baptism and possibly ambush, folded into one week.

He passed the way one passes an exam one has not had time to dread. On 3 January, in his first match as Milan's head coach, Juventus were beaten 2-1; three days later came Inter in the final at Al-Awwal Park, and by the restart the derby had gone wrong in the old way — Lautaro Martínez in first-half stoppage time, Taremi two minutes after the interval, two-nil, the cup as good as loaded onto the other half of the city's baggage. What followed belongs in the small anthology of Milanese resurrections: Theo Hernández on 52 minutes, Christian Pulisic on 80, and in the third minute of added time Tammy Abraham — of all the borrowed princes — with the winner. Three-two, and the trophy came home.

No Milan had come from two goals down to beat Inter since 21 February 2004, and the statisticians exhumed the date while the players hoisted the silver; Conceição had been in the job a week and had already won something, which by the standards of Milan's recent seasons amounted to indecent haste. But the desert is a country of mirages, and this one — a cup gleaming above the dunes — promised a spring that never came. It was the first trophy of 2025 and, as the year would insist with mounting cruelty, the only one.

The Rain in Rotterdam

Europe ended in February, in the rain. The Champions League's new geometry had deposited Milan into a knockout-phase play-off against Feyenoord, and fate, who reads the transfer bulletins, had arranged the casting in advance: in January Milan had paid a reported thirty-two million euros to take the striker Santiago Giménez from Rotterdam, adding Warren Bondo from Monza for ten more, while Álvaro Morata went on loan to Galatasaray — so the tie carried the smell of a family feud. On 12 February, on a wet surface at Feyenoord's ground, Igor Paixão struck after three minutes, and the ball — this is the detail the year kept returning to — slipped through Mike Maignan's gloves. One-nil to Rotterdam.

Six days later at San Siro the script feinted toward mercy. Giménez, inside the first minute, levelled against his former club, and the old stadium permitted itself to believe; then, on fifty-one, Theo Hernández was shown a second yellow for a dive, and in the seventy-third minute Julián Carranza headed Feyenoord through, 2-1 on the aggregate, into a silence you could have carved and served cold. Milan were out of Europe before the crocuses, and the season that had promised in Riyadh to be a feast revealed itself as a long Lenten fast.

Note Theo, because the year kept noting him: scorer in the desert comeback of January, expelled in the ruin of February, and not finished with his own subplot. Players are best loved as fallible men, and few of Milan's moderns gave that principle such steady employment as this full-back, who could win a final and cost a tie inside five weeks.

Fifty-One Years, Settled in Rome

There remained the Coppa Italia, and Milan treated it with the seriousness of a man down to his last good suit. Sassuolo were dispatched, then Roma, then Inter over a two-legged semi-final won on aggregate — a derby scalp that briefly returned colour to Milanese cheeks — and so to Rome on 14 May, the Stadio Olimpico, 68,490 souls beneath the pines. Bologna waited, and history with them: no major trophy in fifty-one years, nothing since 1974, and destiny takes a keen professional interest in round numbers.

The goal, when it arrived on 53 minutes, was a small essay on Milan's season: a challenge by Theo Hernández on Orsolini, the ball loose, and Dan Ndoye arriving to write his name into Bolognese legend. One-nil, no reply; the red-and-blue half of Emilia went home to a celebration half a century in the preparing, and Milan to the final table. It made pitiless reading: eighth place, 63 points from 38 matches — eighteen won, nine drawn, eleven lost, sixty-one scored, forty-three conceded — and, for the first time in years, no European football of any kind waiting in the autumn.

Above them the peninsula staged its own operatic finale: Napoli, under Antonio Conte, took the scudetto on the final day with 82 points, a fourth title for the city of Vesuvius, pipping Inter on 81 — Inter, who then lost the Champions League final in Munich 5-0 to Paris Saint-Germain, a humiliation so complete it nearly redistributed sympathy. The Champions League places went to Napoli, Inter, Atalanta and Juventus; Milan's name appeared on no continental list. Amid the wreckage one man went on doing clean work: Christian Pulisic, the quiet American, the club's top scorer with 11 league goals and 17 in all competitions, a craftsman finishing his joints properly in a workshop with half its roof gone.

Tare, and a Man Who Knew the Corridors

Great houses answer shame in one of two ways: they change the wallpaper, or they rebuild the kitchen. Milan chose the kitchen. On 26 May Igli Tare, who had spent more than fifteen years as Lazio's sporting director learning where Serie A hides its truffles, was appointed the first team's sporting director; and on 30 May back through the gates came Massimiliano Allegri, who had coached the club from 2010 to 2014 and left behind the scudetto of 2010-11 and the Supercoppa that followed it, hanging his coat at Milanello eleven years after taking it down, in a club whose corridors he could walk in the dark. Above them the chart was American and unchanged: RedBird Capital Partners, the fund of Gerry Cardinale, holder of 99.93 per cent of the shares, with Giorgio Furlani as chief executive, Zlatan Ibrahimović prowling as senior advisor and Paolo Scaroni presiding in the boardroom.

The summer market read like surgery rather than shopping. Out went Tijjani Reijnders to Manchester City for fifty-five million — seventy, the reports said, if every bonus ripened — Malick Thiaw to Newcastle for thirty-eight, Noah Okafor to Leeds for nineteen, with Morata's loan carrying him off besides; in came Samuele Ricci from Torino for twenty-three, Christopher Nkunku from Chelsea for thirty-seven, Ardon Jashari from Club Brugge for thirty-four, Pervis Estupiñán from Brighton for seventeen, Adrien Rabiot from Marseille and Koni De Winter from Genoa — a whole pensione of newcomers in the vacated rooms, the January arrival Santiago Giménez among them — and, above them all, on a free transfer that cost nothing and meant everything, Luka Modrić. Mike Maignan kept the captain's armband, Rafael Leão the vice-captaincy and Matteo Gabbia the rank behind him — an order of succession that told you where this Milan's certainties resided: at the back, in the gloves — and the whole apparatus was pointed at a single campaign with no European midweeks to bleed it: one target, and Allegri taking aim.

One consequence of the Reijnders sale never reached the Italian back pages. In Zwolle, where the Dutchman had spent a boyhood year in the colours of the amateur club CSV'28, FIFA's solidarity mechanism handed the little club some two hundred and seventy-five thousand euros out of the English millions — its second dividend from the same boy, the first having come when Milan bought him from AZ in 2023. The chairman, Jakob Sijbersma, called it a huge boost; the money was earmarked for a larger canteen, better changing rooms, and a permanent tribute to Reijnders at the sports park where he had been a boy among boys. Great transfers are reported as figures on a screen; they land as a wall and a plaque in a Dutch suburb.

And on 10 July, Theo Hernández completed his own departure, to Al-Hilal for twenty-five million — six seasons, 262 appearances, 34 goals, the scudetto of 2022 and the Supercoppa of January, a last season spent in part on the bench. He did not go quietly. His farewell letter carried a dart for the men upstairs: 'La dirección que ha tomado el club... no respetan los valores que me llevaron a fichar' — the direction the club has taken does not respect the values that led him to sign — and the only executive he thanked by name for vision and leadership was Paolo Maldini, dismissed two summers before. Of the owners, not a word. The subplot promised in February had its last line, in Spanish.

The Watchmaker of the Adriatic

On 14 July the club confirmed what the city had been savouring for a month: Modrić — captain of Croatia, winner of the 2018 Ballon d'Or, veteran of thirteen seasons and of every major trophy Real Madrid had to give — had signed until 30 June 2026, with an option for a further year, for a reported three and a half million net, and had taken the number 14 shirt. He would be playing Serie A for the first time in his life, and put pen to Milanese paper only once his Club World Cup duty with Real was finished — a scruple that tells you the whole man. He was thirty-nine; he would turn forty on 9 September, mid-season, as watchmakers do — without stopping the mechanism to mark the hour.

Understand what he chose. Not a coronation, not a farewell tour beneath palm trees: a rebuilding club with no European football, the eighth-placed patient still on the table. He spoke of Milan as a club resembling Real Madrid in stature and history — which from another mouth would be flattery, and from his was a diagnosis. From the first weeks he became what Allegri required at the centre of the reconstruction: the old watchmaker bent over the movement of a team, setting its escapement, teaching the minute hand not to hurry. Milan has signed many stars; rarely has it signed so much time in a single pair of boots.

The Long Way Round to Perth

The new Milan was assembled, fittingly, on the far side of the planet and the far side of the clock. Pre-season took the squad along an Asia-Pacific arc: Singapore first, where on 23 July Arsenal won 1-0 at the National Stadium through a second-half goal from Bukayo Saka, before 22,813 — a defeat taken with the shrug pre-season permits, softened by a friendly shoot-out Milan took 6-5 — then Hong Kong, where on 26 July at Kai Tak Stadium, before 49,704, Milan beat Liverpool 4-2: Rafael Leão on ten minutes, Ruben Loftus-Cheek after the interval, and Noah Okafor, in his final weeks as a rossonero, scoring twice, the second in stoppage time.

And then Australia. On 31 July, at HBF Park in Perth, before 19,226 spectators, Milan met Perth Glory, David Zdrilic's A-League side, and were merciless in the way of a team auditioning for its new manager. What had felt like a miracle the first time had, a year on, become something rarer: a habit. The bridge across the world held, and an Australian winter had learned to expect the red and black. Nine goals without reply: Filippo Terracciano after three minutes, Okafor again on 22 and 25, Christian Comotto from the penalty spot on the half-hour, Samuel Chukwueze on 32 — five before the interval — then Leão either side of the evening on 46 and 86, Ricci on 58, Yunus Musah on 80. Tomori marshalled, Estupiñán overlapped, and Perth's scoreboard operators earned their wage twice over.

It was Milan's second visit to that western city in fourteen months: on 31 May 2024, at Optus Stadium, the club had played Roma in the match that marked its first appearance in Australia in thirty years. The stands at HBF Park told the truer story — the rossoneri of the antipodes, the faithful who keep Milanese time under a southern sky, for whom the club comes in the flesh once in a generation and whose kick-offs otherwise fall at hours no European has to consider. When Leão struck his second, the noise had an Italian accent and an Australian heart.

A Hundred Years of Hospitality, Repaid

Allegri's second reign opened at San Siro on 23 August against newly promoted Cremonese, and the gods of football, who read scripts chiefly in order to mock them, produced their finest work of the year. Federico Baschirotto headed the visitors in front; Strahinja Pavlović equalised before half-time, and reason appeared restored; then Federico Bonazzoli arched backwards into the sort of overhead kick that is performed once and replayed for a decade. One-two. Cremonese had not beaten Milan in Milan since 1925-26, when the rossoneri still played at the Campo di viale Lombardia — a hundred years of hospitality settled with an overhead kick — and San Siro's 75,011 filed out with the silence of a congregation that has watched its new priest drop the chalice.

What followed was the purest Allegri. No panic and no proclamations: only the slow lowering of the temperature, the shortening of the team, the restoration of that old Italian premise by which a match not lost is half-won. With no European midweeks to bleed the legs, the reshaped side — Modrić conducting, Ricci and Jashari learning the tempo, Pulisic finishing what others began — began to climb, and by deep autumn the eighth-placed invalid of May was taking the staircase two steps at a time.

The Rebound, the Save, and the Selling of San Siro

The proof arrived on 23 November, matchday twelve, in the Derby della Madonnina. Yann Sommer could only parry Alexis Saelemaekers' shot, and Pulisic — who else, in this of all years — reached the rebound first on 54 minutes; then, on 74, Hakan Çalhanoğlu stepped up to a penalty given by video review and Mike Maignan, whose gloves had betrayed him in the Rotterdam rain nine months earlier, pushed it away as though answering the whole year with one dive. One-nil, and Milan rose to second on 25 points, level with Napoli and two behind Roma; November closed with Allegri named the league's Coach of the Month, and the winter break came with the Rossoneri planted among the leaders.

The city, meanwhile, was settling a much older argument with itself. Through 2025 Milan and Inter pressed the comune to sell them the San Siro area, where they intend to raise a new shared stadium; on 30 September, at three in the morning, after a debate of nearly twelve hours and a council vote of twenty-four to twenty, the administrators approved the sale, and in November the two clubs completed the purchase of the stadium and the land around it for a hundred and ninety-seven million euros. The deadline had been an exquisitely Italian one: the paperwork had to be done before 10 November, when the second tier would pass into the custody of the heritage laws and become, in the eyes of the state, undemolishable. The drawings promise an arena of some seventy-one and a half thousand seats by Foster + Partners and Manica, at a cost approaching 1.2 billion euros, standing in time for the European Championship of 2032, which Italy is to co-host with Turkey; the ninety-nine-year-old Meazza is to come down in the early thirties, a fragment kept back for a commercial and entertainment quarter. Nothing in this city is ever simply demolished. It is renegotiated, like a family story handed down with all the arguments left in.

So ran 2025: a trophy lifted in a desert in January, Europe drowned in February rain, a final lost in Rome in May, an eighth place that tasted of ash — and then, out of the wreckage, the most Milanese of answers: to begin again without announcing it. A watchmaker signed for nothing. A pragmatist recalled from the club's own memory. Nine goals scattered on the far side of the world. A derby taken with a rebound and a save. When the winter break came, nothing had been won beside the January cup, and January by then belonged to a manager already gone; but Milan were second, the mechanism was ticking, and a city that had spent May listing what it had lost spent December wondering what it might still be owed.