After missing out on all European competition for the first time in more than a decade, Filippo Inzaghi has the unenviable task of carrying AC Milan out of metaphorical purgatory and back into the limelight.
Not since the early 1980s when the squad was relegated to Serie B has Milan had such a tough time domestically and on the European level. Their worldwide appeal has dropped considerably, and they've lost the ability to field two world-class starting XIs at any given moment.
Inzaghi was brought in to replace Clarence Seedorf after management knew they'd had enough after only giving the Dutchman six months in charge of the club.
The only experience Inzaghi has in coaching is with Milan's youth side, and it might have been an ideal platform for the coach to familiarize himself with certain youngsters and bring them up through the ranks.
That being said, Adriano Galliani and Silvio Berlusconi know that the Rossoneri's DNA is in the Champions League, and anything else is considered a disappointment.
Only Real Madrid have more Champions League titles than Milan, so a competition without the Rossoneri just doesn't feel right.
The problem with achieving a third-place finish in Serie A is that the other top teams in Italy have strengthened significantly.
With Juventus still favored for the Scudetto despite switching coaches and hiring Massimiliano Allegri, the battle for the other two Champions League spots will be between the likes of Napoli, Roma, Fiorentina, Inter and Milan.
With the league so competitive at the top, getting back into the Champions League will require Milan to make a few new moves.
According to Sky Sport Italia (via Forza Italian Football), the club is close to bringing Colombian left-back Pablo Armero on loan from Udinese, and the Rossoneri have already signed Paris St. Germain pair Alex and Jeremy Menez.
What do you consider a successful season for Milan?
The final piece to the puzzle might be a goalkeeper. Christian Abbiati is in the twilight of his career, Gabriel is too inexperienced and Michael Agazzi has been woeful in the summer friendlies.
Knowing this, it's no shock to see the likes of Diego Lopez and Mattia Perin linked to the club, per Calciomercato.com (in Italian).
Their summer friendly tour in North America started disastrously, as Milan lost their first three games in embarrassing fashion, conceding 10 goals while only scoring one. Fortunately, Milan managed to restore some confidence after beating Mexican side Chivas Guadalajara 3-0.
With Serie A being competitive, Inzaghi will need to figure out how to get the best out of this group rather quickly. There is plenty of skill in the attack, but a few pieces still remain.
The proud history of the club and expectations from the board signal that nothing less than a third-place finish will be considered a success.