AC Milan's position in the managerial market was clarified recently when owner Silvio Berclusconi said: "We will try to sign Pep Guardiola" (via Football Italia). This was as clear a sign as there has been so far that this move really could happen.
A recent upturn in form has seen the Rossoneri climb to seventh in Serie A, beat champions Juventus and qualify for the knock-out stages of the Champions League, but it seems current coach Massimiliano Allegri will be out of a job regardless if they can sign the Spaniard.
"If" is the operative word, however. After stunning success with Barcelona, Guardiola is the hottest property in European football right now, and there is a whole host of clubs lining up to put him in charge.
Berlusconi qualified his statement by saying "...but Manchester City are in pole position,” and Milan will have to overcome clubs who have much larger coffers if they're to get their man.
Berlusconi's intention is one thing but he is no longer able to back up his will as he once did.
Yet, the mooted move does seem to have credibility.
The first firm indication of the seriousness of Milan's designs was La Repubblica's story that Il Diavolo had offered Guardiola a "four-year contract worth almost €25m" (via Football Italia). By turning a profit in their summer transfer business, Milan are in a decent financial fairplay position. If they choose to use this surplus for a manager rather than a player, the money mentioned could be plausible.
Further credence was given to the rumour by former Barcelona President Joan Laporta's assertion that Guardiola "loves Italy and would get along with Silvio Berlusconi" (via Football Italia). Whether or not he would enjoy the opinions of the notoriously outspoken former Prime Minister if things at the San Siro started to go badly is another matter, but the association with Italy is a valid one.
Laporta went on to say that "Pep loves Italy and the passion is mutual. Just think that when we travelled with the team, Pep would only read the Italian newspapers."
This affinity was likely to have been created during the Spaniard's time playing for Brescia, during which time he forged relationships with both coach Carlo Mazzone and the great Robert Baggio.
It seems that, if anything does, this will be the factor that works for the Rossoneri. English clubs such as Manchester City and Chelsea could presumably easily exceed the amount of money offered by Milan, but the climate—both footballing and otherwise—may not appeal to the Spaniard.
Italy is far more similar to Spain and Pep already knows he likes the region (Brescia is only about 50 kilometres from Milan).
I have spoken here about why the move would benefit the Rossoneri, but the club also have one other advantage over the English teams in their attempt to lure Guardiola: Pep has already coached one of Europe's great teams during his side at Barca, has achieved almost everything possible in club football, but adding a team with the history and stature of AC Milan to your resume is still a draw for anyone looking to add to his legacy.
Chelsea and City may currently be two of the richest teams in world football but the historical size of both clubs is severely lacking in comparison to a giant like Milan.