Five Times, and the Same Half Smiling
Riyadh in January; the fifth of February; the tenth and the sixteenth of May; the sixteenth of September. Five times in one calendar year the two tribes of Milan were shut into the same ninety minutes — once in the Arabian desert for a Super Cup, twice for league points, twice for a place in the Champions League final — and five times Internazionale came out ahead. A derby is a family argument conducted in public, and in 2023 one side of the family did all the talking.
And yet to call the year humiliation would be to read the scoreline and skip the match. This was also the year the Diavolo went deeper into Europe than at any time since the Athens night of 2007; the year Rafael Leão, the loping Portuguese who plays as if the pitch were slightly downhill whichever way he faces, bound his future to the club until 2028; the year the reigning champions of Italy surrendered their title to a Napoli drunk on its first scudetto since 1990 and still finished fourth, seventy points, twenty wins, back among Europe's aristocracy. Triumph and grief came in by the same door; to understand the New Rossoneri you must hold both in the mouth at once.

Sandro Tonali and Rafael Leão at the Stadio Giuseppe Meazza on 23 April 2023, during Milan-Lecce. Within six weeks Leão had signed to 2028 with a €175m release clause; within three months Tonali, the Brescia boy who had grown up a Milan supporter, was sold to Newcastle United. The same photograph holds the man Milan kept and the man Milan sold.
Saggittarius A, via Wikimedia Commons — CC BY-SA 4.0
Two Evictions in One Week
The year began with two evictions inside seven days. On the eleventh of January, at San Siro, Torino came for a Coppa Italia round of sixteen and stayed deep into extra time, and although the granata finished with ten men it was they who scored — Michel Adopo, 114th minute — and Milan who went home, out of the cup at the first hurdle, beaten 1-0 at home by ten men. There is a particular Lombard silence that follows such evenings, and it had barely thawed when the squad flew east.
On the eighteenth, at the King Fahd International Stadium, the first derby of the year was played on another continent, the Supercoppa Italiana having become a travelling exhibition. Federico Dimarco after ten minutes, Edin Džeko after twenty-one, Lautaro Martínez to finish it: 3-0, Inter's second consecutive Super Cup, a trophy lost not narrowly but categorically. By the fifth of February, when Inter took the league derby 1-0 as well, the pattern of the year had announced itself the way frost announces itself on a window — quietly, completely, before anyone had noticed the temperature drop. The defending champions of Italy were defending nothing; Napoli were away over the horizon toward a title theirs by right and by margin, their third ever, and Milan's winter business became the salvage of fourth place: 70 points from 38 games, 64 goals scored, 43 conceded. Championships are operas; fourth place is a queue at a ticket window. That year, it was the ticket that mattered.
The Road Back to the High Table
For while the league was being lost the continent was being remembered. On Saint Valentine's night, the fourteenth of February, Tottenham Hotspur came to San Siro for a round-of-sixteen first leg and were met after seven minutes by a goal from Brahim Díaz, a small man's goal in a big man's stadium, and that solitary strike proved the entire tie: in London on the eighth of March Milan defended the nought-nought with the patience of a fisherman on the Ticino, and passed through 1-0 on aggregate. European football at this altitude is a siege diet, and Milan, sixteen years eating poorly on the continent, had not forgotten how to ration.
Then came Napoli, the champions-elect, in a quarter-final that was really a referendum on the Italian season. In the first leg at San Siro on the twelfth of April, Ismaël Bennacer scored from Leão's invention and Zambo Anguissa collected a red card, and Milan carried a 1-0 lead south. The second leg in Naples on the eighteenth was the kind of night Gianni Brera's vocabulary was built to hold: Olivier Giroud, the old Frenchman with the profile of a Roman consul, had a penalty saved and then scored anyway before the interval; Victor Osimhen equalised in the third minute of added time; and in between Mike Maignan — the goalkeeper as final argument — saved a late Khvicha Kvaratskhelia penalty that would have turned the tie. 1-1 on the night, 2-1 across the two legs, and Milan were in a Champions League semi-final for the first time since the club last owned the trophy itself.
The Euroderby: Two Nights, One Stadium, No Mercy
The draw, with the sense of theatre fate reserves for cities that think they have suffered enough, produced Inter. A European Cup semi-final between the two halves of Milan, both legs in the one stadium they share like an old couple sharing a bed and a grievance: billed as the Euroderby, it stopped the peninsula dead.
It lasted, as a contest, eleven minutes. On the tenth of May, in the first leg, Edin Džeko scored in the eighth minute and Henrikh Mkhitaryan in the eleventh, and Milan — nominally the home side, before their own curva — were two goals down before the tie had drawn breath. They did not recover, in that match or the next: on the sixteenth, with the shirts reversed and the same roof overhead, Lautaro Martínez struck in the 74th minute, 1-0 on the night, 3-0 on the aggregate, and Inter walked on to their first final since 2010 while Milan walked the shorter, infinitely longer walk down the same corridor. That Inter then lost the final 1-0 to Manchester City consoled nobody: the Diavolo had reached a Champions League semi-final, a genuine resurrection after sixteen thin years, and would be remembered chiefly as the landscape through which the neighbours marched. Football keeps a cold memory. It remembers how far you went and who stopped you, and it says the second thing louder.
The Fourth, the Fifth, the Twelfth of June
June opened with a goodbye nobody in the stadium had been warned about, his own family included. On the fourth, after Milan had beaten Verona 3-1, Zlatan Ibrahimović walked to the middle of San Siro beneath a single word hung the whole width of the Curva — Goodbye — and stood there weeping. "Det är dags att säga hej då till fotbollen, men inte till er," he told them: it is time to say goodbye to football, but not to you. He shaped a heart with his hands, and Leão ran across the grass to hold him. At the press conference he confirmed what the tifo had announced — the day was his last as a professional — and said he was glad and proud it had lasted as long as it had: twenty-four years, Malmö to this.
The club allowed the tears one day. On the fifth, after a strategy meeting with Gerry Cardinale — the owner whose RedBird Capital had bought the club the previous August — Paolo Maldini was told his work as technical director was finished, the club confirming it in writing the next morning; and Ricky Massara, the sporting director who had built the scudetto squad beside him, went with him. One does not need to editorialise; the noun suffices. Maldini. The surname that had run through the club the way a watermark runs through good paper, the man the tifosi called Mr. Milan, dismissed after a meeting that went badly, with chairman Paolo Scaroni and chief executive Giorgio Furlani stepping into the space he left. The backlash from the faithful was heavy, immediate, and not really about football. It was about whether a club is a lineage or a portfolio, and the answer, in the sixth month of 2023, came without ceremony.
Seven days later the question became bereavement. On the twelfth of June, Silvio Berlusconi died at eighty-six. Whatever Italy made of the man — and it made of him everything it is possible to make of a man — the football club knew what it owed him: rescued from the edge of bankruptcy in 1986, owned until the Chinese sale of 2017, eight league titles, five European Cups, the greatest sustained splendour any club of the twentieth century's end could claim. Carlo Ancelotti was among those who paid tribute, and for a few days the arguments of the present were suspended while the city buried the impresario of its grandest opera. In one week Milan had lost the father of its modern empire and dismissed the son who embodied it. The old Milan, the Milan of dynasty and blood-memory, ended that June: not with a match, but with a banner, a meeting and a funeral.

Mike Maignan in the Milan goal at San Siro on 13 March 2023, against Salernitana. Five weeks later, in the Champions League quarter-final second leg in Naples, he saved Khvicha Kvaratskhelia's penalty to send Milan through 2-1 on aggregate and into their first European semi-final since 2007.
Calciopedia, via Wikimedia Commons — CC BY-SA 4.0
The Boy Who Wrote to Saint Lucy
And still June was not done. Sandro Tonali was born in Lodi, in the flat country south of the city where Milan is not a team but a denomination, and schooled in the academy at Brescia. As a child, in the custom of those Lombard provinces where the gifts are brought not by the man in the red coat but by Santa Lucia, he wrote the saint a letter asking to become a professional footballer — and, while she was about it, for a Milan kit. His grandmother Gina kept the letter. The saint, unusually punctual, delivered on both counts. He arrived on loan from Brescia in September 2020, made the move permanent, took the No. 8, and in 2021-22 drove the midfield of the side that won the club's first scudetto in eleven years — a tifoso in the team of his own devotions, the rarest thing a football club possesses, because it cannot be bought. It can, however, be sold.
In the summer of 2023, with the balance sheet requiring what balance sheets require, Tonali was sold to Newcastle United and their Saudi-backed project for seventy million euro, with ten million more in add-ons should the clauses ripen — a figure that made him the most expensive Italian footballer the game had yet produced. Newcastle announced him on the third of July, not two months after his twenty-third birthday: the boy who had asked a saint for one shirt, the man many had hoped would carry the armband as a bandiera for fifteen years, packed for the North Sea. The fee was enormous, the logic impeccable, the loss total, and all three are true at once. That is the RedBird era in a single transaction: nothing about it was wrong except everything the supporters felt.
Seven Strangers and an American Summer
The Tonali money did not sit idle; Furlani's Milan spent it widely and on the young. In came Christian Pulisic from Chelsea for some twenty million, Tijjani Reijnders from AZ Alkmaar, Ruben Loftus-Cheek from Chelsea too, Samuel Chukwueze from Villarreal, Yunus Musah from Valencia, Noah Okafor from Salzburg, Luka Jović on a free — a squad rebuilt in a single window, joining the previous season's investments in De Ketelaere, Thiaw and Origi. Out, alongside Tonali, went Ante Rebić to Beşiktaş, and the great Swede to the retirement announced on the grass in June, taking the last echo of the dressing-room voice that had scolded the 2022 scudetto into existence.
One arrival carried a story from the club's own attic. Reijnders cost twenty million, signed until 2028, took the number 14, and turned down interest from Barcelona to do it. His father Martin — once a striker at PEC Zwolle, now his son's agent — had grown up worshipping Marco van Basten, and would now watch his boy wear that man's shirt. "Mooi dat ik ga spelen bij de club waar deze drie grootheden hebben gespeeld," the son said — beautiful, that I am going to play at the club where those three greats played — meaning Van Basten, Gullit and Rijkaard. Seven years earlier he had been working a till in an Aldi.
The new company rehearsed in America, on the Soccer Champions Tour, and won none of the three: Real Madrid 3-2 at the Rose Bowl in Pasadena on the twenty-third of July, after Tomori and the teenaged Luka Romero had put Milan in front; Juventus 2-2 at the Dignity Health Sports Park in Los Angeles on the twenty-seventh, before a curious eight thousand, the shoot-out going to the bianconeri; Barcelona 1-0 at the Allegiant Stadium in Las Vegas on the first of August, settled by Ansu Fati in the Nevada heat. Nobody in Lombardy mistook a July scoreline for prophecy. One piece of continuity survived, and it was the most important: on the second of June, after months of difficult negotiation, Rafael Leão signed until 2028, a release clause of 175 million euro standing over the contract like a customs post. Serie A's most valuable player for 2021-22 and top scorer of Milan's 2022-23 league campaign with fifteen, he stayed when staying was no longer to be assumed. In a year of severances, one knot held.
The Fifth Derby, and a Field in San Donato
Autumn tested the new spine and found it unset. On the sixteenth of September the fifth derby of the calendar year completed the whitewash in the cruellest register yet: Inter 5, Milan 1 — Mkhitaryan twice, Thuram, Çalhanoğlu from the spot, Frattesi in added time, with Leão's reply a lone candle in a gale — Inter's fifth consecutive victory in the derby, a run neither half of the city had managed before, and the only mercy was that the year had no sixth meeting to offer.
Not everything that autumn was penance. Reijnders went straight into the side and stayed, three starts in a row, an assist on his Serie A debut against Bologna, and a nickname from a children's television squadron: "Ik word Power Reijnders genoemd, dat is wel lachen" — they call me Power Reijnders, which is a laugh — he told NOS, adding that Milan was a world city, that "Hier zie ik mezelf nog wel een paar jaar spelen" (here I can see myself playing a few more years), and that the season's target was the scudetto. In Europe the new Milan were braver and unluckier. Group F was a customs queue of the continent's aristocracy — Borussia Dortmund, Paris Saint-Germain, Newcastle United, the last now employing a certain midfielder from Lodi. Milan drew 0-0 at home to Newcastle and 0-0 in Dortmund, were dismantled 3-0 in Paris, then beat PSG 2-1 at San Siro through Leão and the old consul Giroud. Dortmund won 3-1 in Milan, Giroud missing a penalty and Chukwueze scoring, and it came down to St James' Park on the thirteenth of December: Joelinton, then Pulisic, then Chukwueze in the 84th, Milan winning 2-1 in the pit of the Geordie noise — and eliminated anyway, third on eight points behind Dortmund's eleven and PSG's eight, consigned with Newcastle to the exit and Milan to the Europa League. A victory that consoled nobody: the year's whole character, stated once more.
Off the pitch, the club was quietly redrawing its own map. On the eighth of June, by public deed, it had bought ninety per cent of SportLifeCity, the company holding the land in the San Francesco quarter of San Donato Milanese, out in the southern suburbs, where the standing plan had been for a modest arena of some twenty thousand seats; and in the last week of September Paolo Scaroni confirmed that the papers were with the comune for something larger — a club-owned stadium of around seventy thousand, with headquarters and museum alongside. Read that against the rest of the year and the shape is unmistakable: a club detaching itself, joint by joint, from every structure it had shared — the stadium, the city supremacy, the dynastic past, the boyhood heart of its midfield — and wagering that what it built alone would be worth the solitude. So the twelve months close: fourth in the league, semi-finalists in Europe, nought from five against the neighbours, one grave, one dismissal, one letter to Saint Lucy returned to sender. Out there the ground bought in June is still only ground, flat and unlit. The drawings are with the comune. Both halves of the city are watching to see what stands up out of that field.

Ruben Loftus-Cheek listening to Stefano Pioli on the San Siro touchline, 19 September 2023, as Milan opened Champions League Group F with a goalless draw against Newcastle United. The rebuilt midfield bought with the Tonali money would finish the group third behind Dortmund and PSG, and fall into the Europa League.
Saggittarius A, via Wikimedia Commons — CC BY-SA 4.0
Sources
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- 2.Sky Sports — Euroderby second leg, Lautaro Martínez winner, Inter through 3-0 on aggregate
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- 4.AC Milan official — Coppa Italia round-of-16 exit to Torino after extra time, 11 January 2023
- 5.AC Milan official — quarter-final first leg win over 10-man Napoli, Bennacer goal, 12 April 2023
- 6.AC Milan official — Rafael Leão contract renewal to 2028, announced 2 June 2023
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- 8.CBS Sports — Sandro Tonali's boyhood Milan story and the sale to Newcastle United
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- 10.UEFA — Newcastle vs Milan, 13 December 2023, final Group F matchday
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- 15.Wikipedia, San Siro — Scaroni's September 2023 filing for a 70,000-seat stadium at San Donato Milanese
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- 17.NOS — Tijjani Reijnders' move from AZ to Milan: €20m fee, deal to 2028, shirt 14, his father Martin and Van Basten
- 18.NOS — 'Power Reijnders': the dressing-room nickname, the assist on his Serie A debut against Bologna, his first Milan autumn