Adriano Galliani has lived through some momentous times at Milan, but nothing could have prepared Silvio Berlusconi’s right-hand for the battle he could never win in the twilight years of his professional life.
The Rossoneri chief executive has stood beside the club owner for nearly 28 years and, as both of them like to proclaim, turned the fallen Milanese giants into the most successful club in the world as they lifted 28 trophies. But for all the battles won on the pitch, the war in the boardroom was always going to be lost once Berlusconi’s daughter Barbara took her first steps in the family business.
Berlusconi senior’s own political and legal problems paved the way for Barbara to fill the void at Milan and, at 28, her ideas of how the club should be run did not sit well with the elder statesman.
Her pointed criticism of the transfer market and, in particular, the €12million spend on Alessandro Matri for a return of one goal so far this season piqued the master wheeler-dealer, who can list a horde of big-name signings including Ruud Gullit, Marco van Basten, George Weah, Zlatan Ibrahimovic and Alessandro Nesta to name but a few. That's not to mention virtual unknowns such as Andriy Shevchenko, Kakà and Thiago Silvio, who have gone on to become world stars.
For decades, Galliani was the man who ran the show and was considered the best transfer negotiator in the game. But recent seasons have seen his star fade somewhat, especially when left to shoulder the fallout of Ibrahimovic and Thiago Silva's departures, as well as Barbara’s then-boyfriend Alexandre Pato.
Even the arrival of Mario Balotelli didn't meet Berlusconi’s approval, with the owner initially claiming he did not need a “bad apple” in the dressing room. The signings of the likes of Kevin Constant, Francesco Acerbi, Giampaolo Pazzini and Bartosz Salamon, meanwhile, were a long way below the standard of talent once unveiled at Milanello.
The writing had been on the wall for the last month or so as the team lurched from one poor result to another, and after the home defeat to Fiorentina at the start of November, the finger of blame was pointed more and more at Galliani. It was only made worse when Balotelli went off the rails after it had been promised the striker was definitely on the straight and narrow.
There may be other issues behind the scenes that will reveal themselves in future, but when the glamorous young Barbara - or Lady B as the Italian press have taken to calling her - took her place beside the 69-year-old at the Camp Nou for the recent Champions League clash against Barcelona, one could feel the icy blast all the way back to the San Siro.
There had already been plenty of reports in the media about Paolo Maldini taking the role of technical director; a position that had always been denied to the club legend by Galliani who, when the captain retired, claimed there was no such role to be filled.
Barbara and Paolo would be new glamour team, with Clarence Seedorf brought back to the club as coach to replace Massimiliano Allegri who, of course, had been Galliani’s man and someone he had supported last season when it looked like Berlusconi would wield the axe.
Galliani waited until the morale-boosting win over Celtic in the Champions League last week to take the wind out of Barbara’s sails by announcing that he would resign after Milan's final Champions League group stage match against Ajax on 11 December.
He would jump before he was pushed, which must have pleased Barbara no end until Dad stepped in again to arrange one of his famous clear-the-air dinners at his villa in Arcoce. Also present was mediator Bruno Ermoli - a powerful political lobbyist - who stayed for two hours before leaving the Berlusconis and Galliani alone.
Another exit strategy was hatched, although it is still not clear if the split will be amicable or eventually head to another protracted court case. If reports are to be believed, Galliani could walk away with a sum in the region of €50m as a golden handshake: a sum that could buy a couple of star players.
In the meantime, Galliani and Barbara will form an uneasy alliance where both parties share the duties of chief executive, with the former in control of playing matters and the latter overseeing the wider running of the club off the pitch. But it is a mere truce for now, and will only see Galliani further marginalised.
He may hold on until next April and the next club meeting, but that seems unlikely considering that the patch-up in relations proposed by Berlusconi will probably come apart sooner rather than later. The derby on 22 December could finally bring down the curtain on one of the great partnerships in Italian football.
Galliani was on the flight to bottom-placed Catania as Milan attempted to kick-start their domestic season once more. With no away wins in Serie A and just 14 points from 13 matches, Allegri’s men were dwelling in the lower reaches of the table among the other also-rans.
Having gone a goal down it was one of Galliani’s shrewdest signings, Kakà, who led the comeback with a display of class and determination. He rounded it off with the final goal in a 3-1 win after strikes from Riccardo Montolivo and Balotelli against the 10-man opposition, who had Panagiotis Tachtsidis sent-off.
There were none of the exalted celebrations from Galliani that generally follow a moment of Milan triumph, but more a stony acceptance that his time is finally coming to a close.
