Can Massimo Ambrosini help his team supplant neighbours Inter?
One has to cast their mind many years back to remember when the two Milan teams had both conceded the Serie A title so limply.
Ahead of this Sunday's Derby della Madonnina, when the two Milanese titans go head-to-head, a battle befitting behemoths will play out.
But unlike recent years, it won't be a "title decider": with neither team exuding control over the league, this is purely for kudos.
With Juventus sitting pretty at the top of the pile, it's looking as if the league title will not be heading to Milan for a second consecutive season.
It's by no means a foregone conclusion that the title is Turin-bound: last weekend's 1-0 defeat at Roma shows that the Old Lady is vulnerable. However, now is not a good time to herald from Milan.
Both residents of the San Siro have been reduced to scrapping away for a European qualification place. In third and fifth respectively, AC Milan and Inter are looking like sorry shadows of their former selves.
They used to rule the roost: Inter enjoyed four consecutive title wins from 2005-06 until 2009-10. Even after they'd been gazumped, it was AC Milan who usurped them in the 2010-11 season.
But since their domineering campaign last season, when they remained unbeaten throughout, Juventus have proved themselves a real tour de force in Italy.
And the evidence seems to suggest that this year, bragging rights will go to those in black and red.
Nicknamed Il Biscione—"The Big Grass Snake"—Inter Milan used to live up to their moniker: coy and cerebral, they would lie patiently in wait, biding their time, striking fear into the heart of their opponents who knew they could be lethal at any minute.
Nowadays, though, they have the stealth of an elephant: the poise and panache has been replaced by a more wanton desire to clumsily stagger through, with more chance of harming themselves than the opposition.
With only two wins out of seven league games in 2013 and only one solitary victory in their last five outings, Inter Milan are in dire form. They can't muster consistency for love nor money, only demonstrating a penchant for leaving games empty-handed.
Last weekend's 4-1 loss at Fiorentina was a real low point. In years gone by, this would have represented a tough tie for Inter but nothing they couldn't manoeuvre.
Being thrashed 4-1 away from home, though—with Antonio Cassano's late, late goal narrowly saving them from a complete whitewash—was not what fans of the Nerazzurri would want to see become habitual.
As Andrea Stramaccioni readies his men to do battle with their Milanese counterparts this weekend, this does not smack of an opportunity for Inter's fortunes to reverse.
Last night, AC Milan and Barcelona played out a high-octane duel at the San Siro.
In a tie that ran Real Madrid-Manchester United close as the pick of the round, these two European heavyweights, both laden with prestige in this competition, went toe-to-toe in a nervy end-to-end battle.
Like any other adversary who dares to, foolishly or otherwise, stand in the way of the Blaugrana juggernaut, AC Milan were given little chance of taking anything from this first-leg encounter.
Yes, it was at the San Siro, but when has an away tie ever made any difference to Barcelona? On their own turf or on foreign soil, it takes a brave man to bet against them.
So it was enchanting when, with plaudit and superlatives at the ready, AC Milan pulled out a virtuoso display to seal a 2-0 victory.
After second-half goals from Kevin-Prince Boateng and Sulley Muntari—both of whom were plying their trade for Portsmouth in the Premier League only three seasons ago—AC Milan looked every inch the imperious Italian outfit they have been of yesteryear.
However, with the two-legged tie only at half-time, there is still a lot to accomplish.
It's one feat accruing an impressive result in your home stadium—and the home fans appeared an intimidating 12th man, producing an endless cacophony of noise—but to go to the Nou Camp and defend that lead is a momentous task.
Whisper it, but Inter fans may be inclined to support their deadly rivals. The logic is thus: If AC Milan can get a result in Spain and they do progress, the Rossoneri may start to wonder how far they can go in this competition.
If they do eliminate the favourites, they should fancy their chances at vanquishing the whole tournament.
If that does happen, and their priorities change, they may take their eyes off the table. In which case, Inter could steal a march on their opponents.
In the short-term at least, last night's tie will have tired those in red and black.
Finishing sixth last season, Inter were far from qualifying for this year's Champions League.
As consolation, they had the dubious honour of having to overcome Romanian outfit FC Vaslui as to obtain a place in continent's corollary competition, the Europa League.
Following a laboured 4-2 aggregate win—including a 2-2 draw at the San Siro—Inter duly qualified for the much-maligned tournament.
And their ensuing results were impressive: following a draw in their opening group game against Rubin Kazan, they proceeded to win their next three games.
Dropping points in that opening game was to prove costly, however, as the Russian side just pipped Inter to top spot in Group H. Still, Stramaccioni's men had a taste for it: there was potential to go far in this competition.
As the pan-European competitions commenced again after the winter break, Inter found themselves entertaining Romanian opposition again, but this time in the form of CFR Cluj.
Travelling in from Transylvania, Inter sniffed blood. Their 2-0 home win against Cluj proved a Pyrrhic victory; last weekend's 4-1 drubbing against Fiorentina followed.
But a pattern may emerge. In fifth place, and 12 points behind leaders Juventus, Inter's title hopes have all but dissipated for a third consecutive season. Only a point off the last Champions League space—currently being occupied by their co-habitants, AC Milan—qualification hopes remain.
They may want to take stock and instead attempt to vanquish the Europa League.
Despite having won the Champions League in that glorious Jose Mourinho-inspired treble-winning season of 2009-10, Inter have not won the UEFA Cup—the previous name of today's Europa League—since 1997-98.
It would prove a tasty addition to an already bulging San Siro trophy cabinet.
In these two tales of a city, nothing encapsulates the contrasting fortunes than the two different strikeforces.
For AC Milan, with the newlyacquired Mario Balotelli slotting straight in alongside Italian-Egyptian wunderkind Stephan El Shaarawy, it is the best of times.
For Inter, with their experienced yet rigid frontline quad having an average age of 32 and only contributing 24 goals, it is the worst of times.
To expand on that, AC Milan possess a wealth of firepower. Even before they gambled on the prodigious but volatile Balotelli, Milan could boast a strikeforce which included Robinho, Bojan and Stephan El Shaarawy.
Whilst the other two have proved classy but perennially inconsistent, it is the latter who has really shone this season.
Powerful, pacy and with a mohawk as bold as brass, El Shaarawy has filled the void left by Zlatan Ibrahimovic. Enigmatic on and off the pitch, the young Italian—born to Egyptian parents—has so far scored 15 goals in 24 appearances.
Only three goals behind Napoli's Uruguayan genius Edinson Cavani, he may yet take the golden shoe for top scorer.
And even if he doesn't, Milan may have another player in the upper echelons of the scoring charts. With four goals in his three appearances since signing from Manchester City, Mario Balotelli looks happy to be home.
Sunday's tie will prove especially tumultuous for him as he takes on the team that first provided the stage he so craves.
How Inter Milan could sure use his guile and craft now. Their strikers are simply not earning their crust.
With the Argentine pair of Diego Milito and Rodrigo Palacio comprising half of a strikeforce completed by the Italian duo of Antonio Cassano and the newly purchased Tommaso Rocchi, Inter's miserly goal difference of plus-7 hasn't been helped by their profligacy.
With Rocchi yet to find the net in his four appearances since signing from Lazio, it has been down to the creaky triumvirate to carry the mantle.
And with only 24 goals between them—Palacio and Cassano have scored as many as El Shaarawy—they will need the likes of playmaker Fredy Guarin to help their cause on Sunday.
Following Claudio Ranieri's dismissal as Inter manager last March, eyebrows were raised when the club announced that the inexperienced Andrea Stramaccioni would be appointed interim coach until the end of the season.
As well having no professional playing pedigree to boast of—despite being on the books of Bologna, he was forced to retire before his 20th birthday due to a serious knee injury—the 36-year-old did not even have his UEFA Pro Licence.
However, after guiding Inter to sixth place—a feat which although seemingly unimpressive, was nigh on monumental considering the tumultuous performances that had dogged that campaign—as well as defeating rivals Milan 4-2, chairman Massimo Moratti opted to take a chance on the Rome native.
He works in a fashion similar to Andre Villas-Boas of Tottenham Hotspur: exceptional intelligence and meticulous attention to detail compensating for his lack of experience.
Similarly to Villas-Boas, though, he is not quite at the level to steer a world-class team to glory. It is likely that a 4-1 defeat to Fiorentina would not have been quite as severe under the Mourinho regime.
And this Sunday, that inexperience may prove costly. For in the opposition dugout, AC Milan have a manager who knows the ropes, knows the league and has a team drunk on confidence after that victory over Barcelona.
Now in his third season at the helm of the Rossoneri, Allegri has already delivered one title, with the 2010-11 crown being their first since 2004.
Previous spells as manager of Cagliari, Sassuolo and Grosseto compliment a rich and diverse playing career which resulted in 420 appearances for 11 different clubs.
Despite being only eight years older than his adversary, Massimiliano Allegri already gives off the impression of a polished leader.
When not pacing the touchline in his pristine suits, he is delivering virtuoso pre-match press conferences.
Before the Barcelona game, he correctly predicted that his team would only be gifted 35 percent possession, and that they needed to ensure their opposition's lion share was "sterile."
Currently boasting a marginally better head-to-head record—81 wins in all competitions, as opposed to Inter's 77—AC Milan go into this tie with swagger. And much of that comes from their manager.