Alessio Romagnoli Saga Shows Diminishing Powers of AC Milan's Adriano Galliani

Defense has been AC Milan's bugaboo for a long time. The team has a long line of defensive legends in its modern history, starting at Franco Baresi and moving through Paolo Maldini, Alessandro Costacurta and Alessandro Nesta.

After Nesta and Maldini moved to the margins, Thiago Silva took up the mantle and turned into one of the best center-backs in the world. But when Silva was sold to Paris Saint-Germain in 2012—the first real sign that Milan were in financial distress—that tradition collapsed. The men who have started at the back, particularly in the center of defence, have been generally substandard.

Bleacher Report's Anthony Lopopolo elaborated on just why the back line was the club's biggest problem on Tuesday. To sum up, any and all of the defenders on Milan's roster can play an incredible game on their day—but they never have that day more than once or twice in a row.

Milan has addressed their midfield and their forward line so far this transfer window, but a defensive improvement has still eluded them—though it's not for want of trying.

The Rossoneri have been after Roma's Alessio Romagnoli for much of the summer. He's one of the up-and-coming young talents in Italy and has the added benefit of familiarity with new manager Sinisa Mihajlovic, who managed him on loan at Sampdoria last season.

The problem: Roma are unwilling to let him go for anything less than a king's ransom. Milan have made several bids but have been repeatedly rejected. A week ago, the Milan Channel confirmed (h/t Football Italia) that an offer of €25 million—up €3 million from their initial bid—had been refused by the Giallorossi.

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It's easy to see this deal still happening. Milan have been incredibly persistent, and, according to La Gazzetta dello Sport, (h/t Football Italia), Romagnoli wants the move.

It can easily be argued that the €30 million price Roma are seeking is exorbitant, especially in the case of a player who has only been a top-flight starter for one season and has never been capped internationally at senior level. Starting-quality veteran defenders rarely go for that much.

Given Romagnoli's apparent desire to reunite with Mihajlovic, that price is probably going to drop just a bit. SportMediaset reported on Monday (h/t Football Italia) that Milan had improved their bid with €3 million in bonuses on top of the €25 million flat fee.

But there is something about this transfer saga that doesn't sit right. Over a decade ago, when team vice-president Adriano Galliani set his eyes on a target, odds were that the target would be a Milan player—and quickly.

But now Galliani has failed in multiple bids for the same player. During Milan's halcyon days, it was rare to see him lose these battles. A deal for Romagnoli would have been done a week-and-a-half ago.

What's going on here? Why hasn't Galliani been able to get his man?

There are two potential reasons. The first is that he's getting gun-shy. Milan are just coming out of a period of austerity, and Galliani might be hesitant to pull the trigger on such a massive deal—particularly when he's already spent a combined €50 million for striker Carlos Bacca and midfielder Andrea Bertolacci.

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Galliani failed notably at putting together a competitive team on a budget, but it remains to be seen how he will really react now that he can spend money again. The Romagnoli saga is not a good first impression.

The other possibility is something some Milan fans have thought for some time: that the old man has simply lost his touch.

If Galliani loses out on negotiations for Romagnoli, it will be the third player to slip through his fingers this summer. His failure to complete deals for Jackson Martinez (signed from under his nose by Atletico Madrid) and Geoffrey Kondogbia (by archrivals Inter) was a significant stain on his record.

In the days of Carlo Ancelotti and Kaka, Galliani would never have allowed other clubs to run circles around him like that. It is clear evidence that Milan's struggles have affected the transfer market. The lack of Champions League play is a clear impediment, and the name Milan doesn't intimidate in the market the way it used to.

Either of these flaws is a serious one and another sign that the man fans call Uncle Fester has lost his hold on the job. But despite these problems, Milan president Silvio Berlusconi looks content to keep Galliani in his current position.

It's an awkward fit right now, given Galliani is sharing power with Berlusconi's younger daughter Barbara, who handles the business side of the club while Galliani focuses on the team.

But Galliani isn't succeeding on his end. He didn't put together good teams when the money wasn't there, and even when it was he had to resort to Plan B—and in the case of Bertolacci he probably grossly overpaid for it. That Silvio Berlusconi has never considered making a change further cements his status as the symbol of the stagnation that has damaged the team.

Romagnoli's fee will eventually be money well spent. He would be a massive upgrade at the back and significantly improve their chances of a top-five finish. Milan will eventually have to bite the bullet and take him on if they want to be competitive—but they also could have had this done a week ago if the old Galliani was taking charge of negotiations.

If Milan want to see out this rebuilding project, the old guy needs to be put to out pasture.