Fog on the Navigli, Light on the Madonnina
There are years that arrive like guests and years that arrive like verdicts, and 2021 came to Milan as both — a guest bearing gifts long ordered, a verdict on seven seasons of wandering. The city began it under the usual January lid of Lombard fog, the Navigli grey and patient, San Siro emptied by the pandemic so that football was played to the echo of its own instructions; and in February, as if the whole peninsula had decided to send for an administrator, Mario Draghi assembled a government of national unity in Rome. Italy was holding its breath. So, in its own particular fashion, was Milan.
The club that faced the year was no longer the drifting vessel of the middle decade. Elliott Management — the fund of the Singer family, at the wheel since the summer of 2018 — had imposed order on the accounts and patience on the project; Paolo Scaroni presided, Ivan Gazidis administered, and the football itself belonged to Paolo Maldini and Frederic Massara, who had assembled for Stefano Pioli a squad young enough to be laughed at and, increasingly, good enough to stop the laughing: Rafael Leao, Theo Hernandez, Sandro Tonali, Fikayo Tomori, and — keeping discipline among the pupils like an old corsair teaching navigation — Zlatan Ibrahimovic, thirty-nine going on immortal. Milan had not tasted the Champions League since 2014. This was the year the door would reopen, though doors at San Siro, as we shall see, have always opened both ways.

Fikayo Tomori at San Siro during Milan 1-0 Torino, 26 October 2021 — Milan in the black third shirt against Torino's granata. Signed on loan from Chelsea in the January window and bought outright for roughly €28m in June, by the autumn he was the spine of Pioli's defence.
Saggittarius A, via Wikimedia Commons — CC BY-SA 4.0
Two Bulls in the Winter Ring
The winter market brought the signing that shaped the whole year, though it arrived without trumpets: Fikayo Tomori, a centre-back on loan from Chelsea with an option of purchase near twenty-eight million euros, quick in recovery and unhurried in judgment, who took one look at the peninsula's forwards and concluded they could be caught. Mario Mandzukic came free on the nineteenth of January and would leave again as a footnote; Soualiho Meite arrived on loan from Torino; but it was Tomori who changed the temperature of the defence, and Tomori whom Milan would buy outright before the summer grew old.
Then came the Coppa Italia quarter-final of the twenty-sixth of January, a derby that belongs less to the history of football than to the history of the ring. Ibrahimovic put Milan ahead after thirty-one minutes, and by half-time the old corsair was nose to nose with Romelu Lukaku, two heavyweight bulls bellowing over the same winter pasture, both booked, neither conceding a centimetre. Early in the second half the Swede lunged at Kolarov, collected his second yellow, and left ten companions to defend a lead that could not be defended: Lukaku equalised from the spot on seventy-one minutes once the video judges had deliberated, and in the ninety-seventh Christian Eriksen bent a free kick that ended the cup and began a grudge.
The league derby of the twenty-first of February settled the winter's argument with fewer theatrics and more cruelty. In an empty San Siro, the pandemic's silence making every instruction audible and every error unforgivable, Lautaro Martinez scored twice and Lukaku once, and Milan lost 0-3 — their heaviest derby defeat in a decade. Inter went four points clear at the summit, and though nobody at Milanello would pronounce the word aloud, the title race of 2020-21 ended that afternoon. What remained was something in its way more important: the road back to Europe's high table.
The English Lesson
Europe that spring meant the Europa League, competition of Thursday nights and long arithmetic. Against Red Star in Belgrade on the eighteenth of February Milan drew 2-2 — an own goal from Pankov, a penalty from Theo Hernandez — and at San Siro a week later drew again, 1-1, Franck Kessie converting from the spot in the ninth minute; three-all across the two legs, and Milan advanced on the away-goals rule, that old actuarial mercy, two away goals against one.
The round of sixteen brought Manchester United and a tutorial in the economics of small margins. At Old Trafford on the eleventh of March, Amad Diallo put United ahead early in the second half, and Milan hunted the game until the second minute of stoppage time, when Simon Kjaer — the Dane who kept the ledger of the defence all year like a village notary — rose and headed the equaliser that kept the tie breathing. A week later at San Siro, Paul Pogba came off the bench and struck shortly after the interval; 0-1 on the night, 2-1 on aggregate, and Milan were out. It was not a humiliation. It was tuition — and the fees would be recouped in May.
Bergamo, the Twenty-Third of May
Everything the season owed came due on its final day, in Bergamo, at the Gewiss Stadium, against the Atalanta of the foothills who had made a province into a European power. Milan needed the result to seal second place, and the man who delivered it was Kessie — twice from the penalty spot, once on the edge of half-time and once in second-half stoppage, each kick struck with the certainty of a man signing documents he has already read twice. Atalanta finished with ten after Marten de Roon's dismissal; Milan won 0-2; and after seven seasons of exile the Champions League belonged to them again.
The ledger of 2020-21 read: second place, seventy-nine points, twenty-four victories, seven draws, seven defeats, seventy-four goals scored and forty-one against, Ibrahimovic top scorer with fifteen in the league and seventeen in all competitions, Alessio Romagnoli wearing the armband. Inter were champions, twelve points up the road on ninety-one, and honesty obliges the chronicler to record it without flinching. But in polenta country that May evening Milan had recovered something no table measures: the right to dine again at Europe's high table, won by a team whose average age suggested it had arrived early for somebody else's dinner.
The Boy Who Left for Nothing
And then, at the very hour of restoration, the house lost its youngest wall. Gianluigi Donnarumma had been born under Vesuvius, at Castellammare di Stabia, on the twenty-fifth of February 1999; Sinisa Mihajlovic had thrown him into the San Siro goal against Sassuolo on the twenty-fifth of October 2015, a schoolboy of sixteen years and two hundred and forty-two days; and for six seasons — some two hundred and fifty-one appearances, eighty-eight clean sheets — he had been the fixed point around which a drifting club rebuilt itself, the captain-in-waiting, the son of the house.
His contract expired on the thirtieth of June 2021, and with Mino Raiola driving terms the club would not meet, he walked to Paris Saint-Germain on a free transfer, a five-year deal signed in the middle of July, six years of homegrown devotion ending without a single euro crossing the counter. The timing was operatic in its cruelty, for that same fortnight the summer belonged to Italy: at Wembley on the eleventh of July, in the final of the European Championship, Donnarumma saved two penalties in the shootout against England — the last of them the decisive kick — and was named the tournament's best player, the first goalkeeper ever so honoured; three weeks later Italian sprinters would set Tokyo's Olympic evenings alight. He was a champion of Europe and a free agent in the same breath. Milan's people did not forgive the manner of the going: when he came back to San Siro that autumn in the shirt of Italy — the sixth of October, the Nations League semi-final, Spain winning 2-1 — the whistles found him from the reading of the teamsheet onward, and the old jibe of 'Dollarumma', minted by the Curva during the contract war of 2017, was taken out and polished again. It would be made flesh two years later, when fake banknotes bearing the name rained onto the San Siro pitch as he returned in the shirt of Paris Saint-Germain.
Nor did he leave alone. Hakan Calhanoglu crossed the city to Inter, also for nothing — a defection measured not in fee but in geography — and Diego Laxalt departed for Dynamo Moscow among the summer's other farewells. Two starters lost for the price of a handshake: the accountants winced, the Curva raged, and Maldini went shopping.
What he brought home was the answer to every lament. From Lille, for around thirteen million euros, came Mike Maignan — soon 'Magic Mike' to the faithful — a goalkeeper who commanded his area like a customs officer and healed the Donnarumma wound with startling speed. From Chelsea came Olivier Giroud, a centre-forward of cathedral timing; Tomori was bought outright for some twenty-eight and a half million; Tonali's deal was made permanent; Fode Ballo-Toure arrived for the flank; and the loan market delivered Brahim Diaz from Real Madrid, Tiemoue Bakayoko from Chelsea, Junior Messias from Crotone and Alessandro Florenzi from Roma. Messias — note the name: even a chronicle must be permitted its foreshadowing.

Olivier Giroud at San Siro on 26 October 2021, the night his 14th-minute goal beat Torino 1-0 and put Milan top of Serie A — a €1m summer signing from Chelsea at thirty-five, whose first four goals for the club all came at home.
Saggittarius A, via Wikimedia Commons — CC BY-SA 4.0
An Autumn Above the Fog
The new season opened like a well-run kitchen, each dish arriving on time. Brahim Diaz won the opener at Sampdoria, 1-0, on the twenty-third of August; Cagliari were dispatched 4-1 a week later; Lazio 2-0 in mid-September; a point carried home from Juventus, 1-1; and then two away performances of real character — 3-2 at Atalanta's Gewiss on the third of October, 2-1 at Roma at the month's end — that announced a young team no longer frightened of the road. The crowds, rationed at first and then swelling as the pandemic's grip loosened, returned to San Siro to find their club at or near the top of the table, carried by Leao's gallops, Theo's cavalry charges down the left, Giroud and the forty-year-old Ibrahimovic dividing the centre-forward's duties between injuries, and Kessie's penalties still arriving like quarterly interest.
The autumn derby of the seventh of November was theatre worthy of the Scala down the road. Calhanoglu, eleven minutes in, scored a penalty against the club he had left in the summer — and celebrated it in front of the Curva Sud with his hands cupped behind his ears, a gesture the old house filed away for later — before Stefan de Vrij turned the game level into his own net in the seventeenth. Then the night found its true protagonist: Ciprian Tatarusanu, the reserve deputising for the injured Maignan, flung himself to save a penalty from Lautaro Martinez, and 1-1 it finished, the two contenders locked together like carriages of the same train.
Late autumn brought the wobble every ascent must survive. Sassuolo came to San Siro on the twenty-eighth of November and won 1-3 — Romagnoli's early goal overturned by Scamacca, a Kjaer own goal and Berardi, the captain sent off for his troubles — and on the nineteenth of December Napoli won 0-1 through Eljif Elmas in the fifth minute, a late Kessie equaliser disallowed by the video judges for Giroud's offside, a verdict that let Napoli slip past Milan into second on goal difference. For three days only: Empoli were beaten 4-2 on the twenty-second, and Milan went to the winter break second on forty-two points, four behind Inter's forty-six, Napoli on thirty-nine and Atalanta close behind — chasers, yes, but chasers with their teeth already in the leader's flank.
Europe's Cold Tutorial
The Champions League, so dearly regained, received its returning pupil with the tenderness of a Prussian schoolmaster. The draw produced Liverpool, Atletico Madrid and Porto, and the campaign opened at Anfield on the fifteenth of September with a 3-2 defeat that was almost a manifesto — Rebic and Brahim Diaz scoring, Tomori putting through his own net, Milan bloodied, brave and beaten. Atletico came to San Siro and won 1-2, Leao's opener answered by Griezmann and a Suarez penalty; Porto won 1-0 at the Dragao; and the return at San Siro yielded only 1-1, Mbemba's own goal the whole of the harvest.
The single victory came where none was expected, at the Wanda Metropolitano on the twenty-fourth of November, and it belonged to Junior Messias — the loanee from Crotone scoring the only goal of the night, the chronicle's foreshadowing redeemed. But Liverpool completed the syllabus at San Siro on the seventh of December, 1-2, Tomori's opener overtaken by Salah and Origi, and the table closed with a cold symmetry: Liverpool eighteen, Atletico seven, Porto five, Milan four — last in Group B with one win, one draw and four defeats, six scored, nine conceded, eliminated without even the consolation of a Europa League parachute. Seven years of absence are not repaid in six matchdays; Europe examined the new Rossoneri and marked the paper promising, with returns required.
The Verdict of December
Around the football, the city argued about its cathedral of concrete. The two tenants of San Siro, both of them title contenders now, jointly pressed their case for a new shared stadium beside the old Meazza — and, in time, for the old ground's demolition — and on the twenty-first of December they announced the design they had chosen: 'The Cathedral', drawn by the Populous studio, a rectangular ark of glass and vertical fins to be raised alongside the ground it was meant to replace. It opened a public quarrel over memory and money that this era has never resolved. It was, in its way, the perfect emblem of 2021: a club, and a city, negotiating between what it had been and what it intended to become.
Judge the year, then, as one judges a hinge: by what it connects. Behind it lay seven seasons of exile, a cup surrendered to Eriksen's free kick, a derby lost 0-3 in an empty house, a beloved goalkeeper gone for nothing. Ahead of it — though the chronicler must whisper, for as 2021 closed Inter led by four and Milan were merely the chasers — lay the May of 2022, when this same young side would finish champions on eighty-six points, a club record for the three-point era, two clear of Inter, and the Madonnina would look down on a city dressed in red and black. The fog of January had lifted by December just enough to show the summit. Milan were climbing.

Gianluigi Donnarumma in Italy colours in Sofia before Bulgaria 0-2 Italy, 28 March 2021 — three months before his Milan contract expired and he left for Paris Saint-Germain on a free transfer, and fifteen weeks before he saved two penalties at Wembley to win Italy the European Championship.
Biser Todorov (User:Biso), via Wikimedia Commons — CC BY 4.0
Sources
- 1.Wikipedia, 2020-21 AC Milan season — 2nd place, 79 points, Tomori loan, Ibrahimovic's 15 league goals, Champions League qualification
- 2.AC Milan official — Atalanta 0-2 Milan, 23 May 2021, Kessie's penalties and the Champions League return
- 3.CNN — Coppa Italia quarter-final, 26 January 2021: Ibrahimovic-Lukaku confrontation, red card and Eriksen winner
- 4.ESPN — Donnarumma's free transfer to Paris Saint-Germain, July 2021
- 5.Wikipedia, 2021-22 AC Milan season — summer rebuild (Maignan, Giroud, Tomori, Tonali), autumn results, Elliott ownership
- 6.Wikipedia, 2021-22 UEFA Champions League group stage — Group B results and final table (Milan 4 pts, last)
- 7.Inter official match report — Derby della Madonnina, 7 November 2021: Calhanoglu's penalty and celebration, de Vrij own goal, Tatarusanu's penalty save
- 8.CNN — Milan and Inter unveil Populous's 'The Cathedral' as the design for their new shared stadium, December 2021
- 9.Reuters — Donnarumma booed by Milan fans on his San Siro return with Italy, Nations League semi-final, 6 October 2021
- 10.AC Milan official — Champions League elimination, Milan 1-2 Liverpool, 7 December 2021