Ever heard the Italian phrase minestra riscaldata?

Basically, it means reheated soup never quite tastes the same.

It came to mind when AC Milan announced they had hired Max Allegri at the end of May.

Max is back for a second stint on the Rossoneri bench, 11 years after his initial spell ended. If history has taught us anything, coaches at Milan do not tend to fare as well second time around.

Milan have often resorted to bringing back old bosses in a desperate attempt to relive a glory era, only for the returns to produce very diminished results.

Nereo Rocco, Nils Liedholm, Arrigo Sacchi and Fabio Capello made the trek back to Milanello a second time (and in Rocco’s case, multiple times), only to sour the brilliance of the original spell.

Rocco, in fairness, bucks the trend somewhat. He originally coached Milan in the early 1960s, delivering their first European Cup in 1963.

He left that summer to take over Torino before returning in the summer of 1967 to take the reins a second time.

And Rocco, one of the pioneers of catenaccio, performed better in his second stint: one Serie A title, two Cup Winners’ Cups, two Coppa Italias, a second European Cup in 1969 and the Intercontinental Cup were all secured in a glorious six-year spell.

Departing in 1974 after disagreements with the board, Rocco returned three more times to ever-diminishing results.

His last stint in 1977 brought one final Coppa Italia, but he could ever recapture the magic.

Liedholm replaced Rocco in the summer of 1977, won the Scudetto in 1979 before leaving to join Roma weeks later. 

Liedholm, who played for Milan from 1949 to 1961, returned in 1984 to oversee three mediocre seasons as they struggled to reassert themselves post-Totonero.

His second spell produced no trophies and he was sacked towards the end of the 1986-87 campaign, with Silvio Berlusconi lining up Sacchi for the following season.

As most know, Sacchi’s first spell in charge of Milan changed the very fabric of the game.

He left in 1991 to take the Italy job, but was coaxed back in the winter of 1996 by Berlusconi as Milan were struggling in the wake of Capello’s departure to Real Madrid.

Sacchi, who by 1996 was already yesterday’s man, was disastrous. He resumed his feud with Roberto Baggio and oversaw Milan’s worst-ever home defeat since the creation of Serie A, a 6-1 demolition by Marcello Lippi’s Juventus.

They finished 11th and were the worst defending champions in the three-points-per-win era for decades (until Napoli in 2023-24).

Sacchi lasted all of seven months before making way for a returning Capello, who fared even worse. Milan finished 13th in 1997-98 and Capello walked away after a single season, never to return.

Now Allegri is walking into a club that in many ways is very different to the one he left in 2014, but is also quite similar.

Allegri left Milan at the onset of the ‘banter era’ years, and there is a fear among Milanisti they are sliding back towards those painful days.

Their best performer in 2024-25, Tijjani Reijnders, has just been sold to Manchester City for an underwhelming figure, while two key pieces of the 2022 Scudetto triumph in Mike Maignan and Theo Hernandez also look set to leave.

Maignan is wanted by Chelsea and with his contract expiring next year, Milan could be strong-armed into selling for a relatively low fee. Hernandez, who has regressed since the departure of Paolo Maldini, is closing in on a return to Spain with Atletico Madrid. Rafael Leao, meanwhile, is thought to be of interest to Bayern Munich. The wolves appear to be circling.

Furthermore, the ultras are in open protest against the current ownership. RedBird have won few fans since buying the club from Elliott Management in the summer of 2022.

On the final game of the season against Monza, a dead rubber of a match with nothing on the line for either side, the Curva Sud organised a walkout after 15 minutes, leaving a banner reading ‘Go Home’ on the seats. A clear message to RedBird for the world to see.

A horrendous season culminated in the defeat by Bologna in the final of the Coppa Italia in Rome, denying them European football next year.

Chaos epitomised Milan’s campaign, and while Elliott got very little wrong upon taking ownership, RedBird have got very little right.

Sacking Maldini two years ago was, in hindsight, a watershed moment they have not really recovered from.

RedBird have prioritised financial prudence over any genuine ambitions at competing at a high level. The old ‘you have to spend money to make money’ adage has seemingly been lost on the current administration.

Under RedBird, there is the sense every player at Milan has his price. Sandro Tonali’s sale was also a key turning point, it was not needed for financial reasons, but was classed as an ‘opportunity’ by Gerry Cardinale.

Milan turned a profit of €4m in 2023-24, but with the lack of European football in 2025-26, most recognised a big sale was imminent. And so it was Reijnders, one of the best midfielders in the league, who was sacrificed.

“Considering the way we are run, it is not necessary to make a sacrifice,” said CEO Giorgio Furlani a mere two weeks before the Dutchman was sold.

City paid €55m plus €15m in add-ons for Reijnders, a ludicrously low figure in the modern market. But the sale will ensure Milan finish the 2024-25 season in the green once more.

Or as some fans label it, the ‘balance sheet Scudetto’.

“Winning championships is obviously an important goal. But you have to balance that with winning smartly,” said Cardinale in a 24-page Harvard Business School study case last year.

To win championships one has to spend money and, crucially, it has to be spent wisely, something Milan have not done.

And so between fan unrest, key players leaving and a downsizing of ambition, this is the Milan Allegri is walking back into: a club in a constant state of flux, one that aligns itself with the Brighton, Bournemouth and Atalanta business model of success, rather than one of seven-time European champions and football royalty.

Former Lazio sporting director Igli Tare has been brought in to rectify the damage done by Furlani and Geoffrey Moncada.

Allegri will, according to reports, have influence on who they bring in this summer.

Naturally, rumour of a move for Adrien Rabiot, who played under Allegri in his second spell at Juve, has spread.

Dusan Vlahovic is another favourite of Allegri’s who could make the move to Milan. The Serb is likely on the outs with the Old Lady after three years of inconsistent performances and with Milan in need of a reliable goalscorer, Vlahovic could be a low-cost option.

One of Maldini’s main gripes about RedBird’s vision was the over-reliance on youth. 

The Milan legend understood dressing-room dynamics better than most, and recognised that while prioritising youth is key, you need experienced players to steer the ship.

It appears the penny has finally dropped with Cardinale, as Milan are now being linked with old heads like Luka Modric, Granit Xhaka and Oleksandr Zinchenko.

Despite their advancing years, all three would bring tactical nous and leadership, elements badly missing from the current crop.

The style under Allegri will not be pretty but it will be effective. His second spell at Juve produced some of the most tepid games of football Serie A has seen in the last decade. Yet he got results in Turin, and that ability to grind it out – no matter how bad the football was – is something Milan desperately need.

The look of Allegri’s squad could change massively by the time a ball is kicked on the opening weekend of the season in late August, so making predictions at this stage would be foolish. But like with Antonio Conte at Napoli last season, Allegri will instantly make Milan a better team.

Can he break the cycle of bad managerial sequels at Milan? Or will he be the latest in a line of legendary coaches who returned only to sully their once-immaculate reputations?

Soup, as they say, never does taste the same second time around.