Juan Rodríguez had never scored in Serie A before May 24. The 20-year-old Uruguayan center back got his first at San Siro in the 57th minute of the season’s last game, finishing a Cagliari comeback that Gennaro Borrelli had started by canceling out Alexis Saelemaekers’ second-minute opener.
Lega Serie A counted the 2-1 result as Cagliari’s first win over Milan at San Siro in nearly 30 years. It also left the Rossoneri fifth, one point behind Como and outside the Champions League.
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RedBird Capital Partners called the season “an unequivocal failure” the next day and dismissed chief executive Giorgio Furlani, sporting director Igli Tare, technical director Geoffrey Moncada and coach Massimiliano Allegri.
The owners had set two targets a year earlier: a return to the Champions League, and a foundation for winning consistently at the top of Serie A. Their statement said Milan had spent most of the campaign in the top two before the final stretch undid it.
Those targets still frame Rúben Amorim’s first season, and they describe two different climbs. The first is within reach, because what sank Milan last spring looks like a collapse rather than a ceiling. The second runs through money, above all a new stadium that so far exists only as a construction site, and the American exchange pricing the title thinks it’s a long way off.
Milan lost the top four in the ten rounds after the derby
The collapse began straight after a high point. Pervis Estupiñán scored in the 35th minute of the derby at San Siro on March 8, Matchday 28, and the 1-0 win took Milan to 60 points. Held over 38 rounds, that rate of just over two points a game comes out at roughly 81, more than Napoli’s second-placed 76 and six short of Inter’s 87.
Milan took 10 points from the 10 rounds that followed. Lega Serie A’s final-day review put that tally level with relegated Cremonese’s over the same stretch, with only Pisa and Verona doing worse. San Siro hurt most, with one point from the last four home matches, the last of them against Cagliari.
Fourth place went instead to a club that had never played in a UEFA competition. A side that is short all year has a ceiling problem. One that holds a top-two rate for three-quarters of a season and then falls apart has a narrower problem, and probably a more fixable one.
Nobody outside the club can say for certain why the spring went wrong, and the owners chose not to find out with the same staff.
Five rounds in, San Siro is paying again
This season’s first evidence goes straight at the home problem. Milan won 2-1 at Torino on Aug. 23, then beat Venezia 2-0 and Lecce 3-0 at home, with Christian Pulisic, Adrien Rabiot and Diego Moreira scoring against Lecce on Sept. 20. Two league games at San Siro have brought two wins and no goals conceded.
The dropped points came on the road, in a 1-1 draw at Juventus on Sept. 6 and a 2-2 at Lazio six days later. That leaves Milan unbeaten in the league and fifth on 11 points, two behind Roma, Inter and Lazio and one behind Cagliari, of all teams.
Five rounds prove very little, and San Siro hasn’t been spotless: Benfica won 2-0 there in the Europa League on Sept. 16. Still, the league points are arriving where last season leaked them, the first thing a recovery has to show.
Amorim was hired for a style, and one chair is still empty
The owners’ answer was wider than a coaching change. Of the four men dismissed the day after the Cagliari game, only Allegri worked on the grass; the others ran the club and built the squad. Milan appointed Amorim on June 16. He won two Portuguese league titles at Sporting and last worked at Manchester United, which dismissed him in January.
Gerry Cardinale was specific about what he wanted: “Rúben believes in high press attacking football with quick transitions that enable greater goal scoring.” Ten days later Massimo Calvelli became chief executive, and Cardinale’s statement on the appointment said “we will play to win, instead of playing not to lose” before naming the pitch as the place that mattered most. Both lines add a style test to the league table.
The squad moved as well. Rafael Leão, whom the club credited with helping win the 2021-22 Scudetto, left for Galatasaray on Aug. 30 after seven seasons. One seat is still empty, though. Tuttosport reported on Sept. 24 that the search for a director to lead the sporting side was still going on, so whoever takes the job will inherit a coach and a squad already in place.
Before Kalshi priced Milan’s title, it went to court over Congress
A blunt outside verdict on Milan’s ceiling comes from an American exchange. On Sept. 24, Kalshi’s contract asking “Will Milan win the 2026-27 Serie A?” last traded at 6 cents, against 60 for Inter and 22 for Roma. Each contract pays $1 if its club finishes champion, so 6 cents reads as roughly a 6% chance.
The top-four market, where the owners’ own target sits, says almost nothing. Only about 135 of Milan’s top-four contracts have changed hands, against roughly 20,000 on the title, and the highest bid of 37 cents sat far below the lowest offer at 78.
Kalshi got to football after a fight over Congress. In 2023 the exchange, which the Commodity Futures Trading Commission regulates, self-certified contracts on which party would control each chamber, and the commission barred them later that year as gaming and activity unlawful under state law.
Jia Cobb, a federal judge in the District of Columbia, set the order aside in September 2024. Kalshi’s contracts, she wrote, did not involve unlawful activity or gaming: “They involve elections, which are neither.”
The appeals court for the D.C. Circuit refused on Oct. 2 to put her ruling on hold, weeks before the 2024 election. Kalshi’s first sports contracts followed in January 2025, according to an April ruling by the Third Circuit, and the feed that returns Milan’s price still answers at an address beginning api.elections.
That win covered elections, not football. The sports contracts ended up in court too, and with some judges siding with the federal regulator and others with state gambling law, whether one like Milan’s may be offered currently turns on which state a customer is in.
So the 6 cents sits on the same cash-settled, yes-or-no design that Kalshi fought for in the Congress case, and weighing it means knowing what a price in cents implies and whether prices like it beat other forecasts. Serie A’s contracts are too young to answer the second question.
Election contracts have a longer record against the polls, and GamingToday looks at that record through the 2024 presidential race, alongside how election prediction markets turn a price into a probability and how they are pricing the Nov. 3 midterms.
Milan’s wage bill points to fourth place
Money accounts for part of the gap that price describes. Calcio e Finanza’s estimates, which SempreMilan broke down player by player on Sept. 10, put Milan’s gross wage bill for 2026-27 at €103.14 million, fourth in Serie A. Inter’s is estimated at €145.8 million, Juventus’s at €145.5 million and Napoli’s at just under €110 million.
Milan’s bill is rising, with net pay up about 16% to €64.8 million, and summer arrivals Gonçalo Ramos and Mario Gila share the club’s top net salary of €5 million with Mike Maignan. On these figures the gap to Inter still comes to roughly €43 million a year in gross wages.
Read that way, the owners’ first target only asks the payroll to finish where it ranks, with the fourth-highest wages taking fourth place. The title asks for more, a finish above three squads that cost more, held over 38 rounds. Roma are managing it for now, top of the table on goal difference with an estimated €92.7 million, the fifth-highest bill in the same ranking.
Milan are out of UEFA’s settlement, but the new stadium is years away
Closing a €43 million gap takes revenue, and Milan start from a cleaner position than some of the clubs around them. UEFA’s financial control body announced on June 17 that Milan had met the final target of their settlement agreement and left the regime.
The same decisions fined Roma €6 million in total, €4 million of it for a squad cost ratio above 70% in 2025. Less than two weeks later, UEFA announced that Juventus had agreed a three-year settlement carrying a €20 million fine, €14 million of it conditional.
None of that frees Milan to spend at will. The club’s own figures tie the squad to its income. Its statement on the 2024-25 financial year said record revenue of €494.5 million, up 10%, had driven more than €250 million of investment over two seasons, and it noted that the balance sheet would only partly offset a season without European income. The club presented last year’s accounts in November, so the figures for that season should follow later this fall.
The stadium is the revenue line that could change the arithmetic. Milan and Inter signed the deed for San Siro and the land around it on Nov. 5, 2025, with Foster + Partners and MANICA designing the new ground, and over the summer the approaches to the old one were reorganized so work could begin on the construction site.
Two days after the deed, both clubs’ presidents told a business forum in the city that they wanted the new ground finished by the end of the decade, and Inter’s president warned that bureaucracy could slow it.
The Associated Press reported an estimate that the arena could bring each club as much as €180 million a year, more than double the roughly €80 million each had been making from San Siro. Until it opens, that money is years away, and this season’s climb has to come from the squad already paid for.
The climb worth judging starts with the run-in
Which climb to hold Amorim to is the fan’s call. The title price will keep moving round by round until the league has a champion, and fans who like a US voice in their feed beside the club’s own can find GamingToday on Facebook.
The more useful test comes in the spring, at home, where last season came apart. If Milan are still collecting points at San Siro when this season’s run-in begins, fourth place is theirs to lose, and fans can fairly hold Amorim to it.
If the home results fade again, the climb is a longer project than one summer’s reset, and patience becomes the honest position.
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