It seemed like the perfect fit. A beloved idol, who spent a decade at such an esteemed club, winning titles and adulation along the way, returns heroically to navigate the sinking ship.
So it was in mid January when Dutch legend Clarence Seedorf dropped anchor in Milan's crumbling harbour, this time as the man at the helm. For a first job in management, they don't come on much choppier waters.
A dominant force not only in national football but European football, a Champions League winner as recently as 2007, the Rossoneri had gone backwards at an alarming rate under Massimiliano Allegri.
Enter the saviour. He started positively, his first game ending in a 1-0 win over Verona at the San Siro.
But football matters cannot be resolved purely on emotion. Their slide towards anonymous mediocrity has not been arrested over the last two months since the four-time Champions League winner's arrival.
The club do not currently occupy a place in the top half of the Serie A table and were comprehensively dumped out of the Champions League by Diego Simeone's Atletico Madrid, currently threatening to divorce Barcelona and Real Madrid from the decade long grip they have had on the Spanish La Liga crown.
With just nine games remaining in the league season, qualification for next year's European elite event looks a nigh-on impossibility.
Managing a club brings with it enormous baggage. There is not only the coaching side of the job, but the unenviable task of keeping an increasingly large squad happy, only 11 of whom can be on the pitch.
To start your career at such an established outfit as the seven-time Champions League winners is as tall an order as they come. And therein lies the problem for Seedorf.
He has no managerial experience to fall back on, no tried and tested method that can pull the club clear of these darkened days.
Everything he is implementing is an experiment. But at such a crucial time, Milan are not after experiments, they are after answers leaving little scope for a much-needed learning curve for their rookie boss.
Italian sports writer Marco Mugnaioli thinks a tactical change of approach may be needed, if not in the coming weeks, then certainly next season.
“He [Seedorf] has decided to play 4-2-3-1 with Balotelli as the forward. But the style isn't working with the players he has and he doesn't seem to understand this.
“He is running the risk of losing the job for next season. Although he was chosen by [Silvio] Berlusconi [the AC Milan president] so I think he'll stay.
“He's very clever and he understands football. He needs time and investment in the type of players to suit his style. Then we can judge him.”
The restoration of Milan will be long, extensive work. Which makes you wonder if Seedorf would not have been better served playing out the final year of his contract with Brazilian club Botafogo.
Certainly, the Dutchman has unfinished business in Brazil. The Rio de Janeiro state championship is scant consolation for a man with a trophy cabinet as deep as Seedorf's.
Last season, the midfielder helped Botafogo qualify for the Copa Libertadores, the South American equivalent of the UEFA Champions League, for the first time since 1996.
Despite wilting slightly towards the back end of the 2013 season, he was hugely influential in the Glorioso's successful campaign last term, acting as a mentor for the younger members of the club as well as a leading light on the field.
Nevertheless, young defender Doria believes the club can go far in the Libertadores even without Seedorf, as reported by Alexandre Braz.
But to have a player of his calibre, experience and technical expertise could only be a positive for the Rio club. Seedorf the player is everything Seedorf the manager isn't, yet at least.
Undoubtedly, the Milan post is an excellent opportunity. Chances to coach one of Europe's finest outfits do not come along every day, and perhaps, the Dutchman thought it too good to refuse.
But after battling for eighteen months with Botafogo and finally managing to propel them forward, it seems a crying shame the veteran isn't still at the club to savour the fruits of his labours.
The Brazilians are well-poised to progress to the knock-out phase of the continental competition. Adding a new medal to his extensive collection may have been just cause for Seedorf staying put, rather than enduring his present storm in unchartered waters.
All quotes were obtained firsthand unless otherwise stated.