You'd think that with the Milan manager having finally obtained a long-term contract and with his club's owner, Silvio Berlusconi, finally being found guilty after appeal of tax fraud and facing a custodial sentence (and the end of his political career), he might have been able to guarantee himself some time and some decision-making power.
Not so, apparently. All summer long, Celtic's opponents on Wednesday thought they had a plan in place. They would push youth and the 4-3-3 system. It worked well last season, after the January signing of Mario Balotelli. Milan shot up from seventh place to a spot in the Champions League. It wasn't just about the former Manchester City striker. Stephan El Shaarawy and Mattia De Sciglio, a pair of 20-year-olds, established themselves as both regulars and Italian internationals. Another Italy player, Riccardo Montolivo, grew into a leadership role in the middle of the park, after a slow start. A talented, but raw, 18-year-old, M'Baye Niang, was lighting up on the wing. All of a sudden, the Rossoneri were both fun to watch and in the ascendancy.
The summer came and the Allegri plan was put into effect. The club would stay within their means and grow through youth. They picked up two more promising young players, Andrea Poli and Riccardo Saponara, with the idea of bringing them along slowly. Nigel De Jong returned after almost a year out through injury to stiffen up the midfield. It was going to be another transitional season but, hey, they were building towards something. And then, in the space of a few days, it all changed.
Out went Kevin- Prince Boateng, to Schalke for £10 million. Milan then took that money and used it to sign a centre-forward, Juventus's Alessandro Matri. And they compounded matters within 48 hours when they re-signed Kaka on a free transfer from Real Madrid.
Kaka's return means Allegri's grand, long-term plan goes out the window. There is only one place the Brazilian can play and that's in the hole. In a 4-2-3-1, which would allow for the continued development of the young wingers, El Shaarawy and Niang?
Theoretically, yes. But the signing of Matri suggests probably not. When you factor in that Milan already have another No 9, Giampaolo Pazzini, currently injured but scheduled to return next month, the probability of a change to the playing system looks even stronger. Every indication is that Kaka is set to play behind a Matri-Pazzini partnership. Which would be fine, if not for the fact that it negates much of the work done in the previous nine months and turns promising kids into frustrated benchwarmers.
The whole affair smacks of the kind of "intuition" that Berlusconi has bestowed on his team from above. Sometimes it works, sometimes it doesn't. Generally, it's unwelcome. And in this case it does little but undermine Allegri's work and authority.
All this would be dubious enough if the "real" Kaka were returning to the San Siro. But we don't know which version we're getting. Four seasons at the Bernabeu have left their mark and not in a good way. The numbers speak of 85 Liga appearances and 23 goals in four years, but in the last three campaigns he made just 40 starts, most of them when Jose Mourinho was rotating his squad.
His decline has been obvious, vertical and difficult to explain. Injuries only tell part of the tale; there have been issues with the tithing to his church and questions about his desire. On the plus side for Milan, he cost nothing and even took a massive pay cut to join, lopping more than 60% off the wages due to him in the final two years of his deal at the Bernabeu. Then there's the instant lift he has given the fan base, largely based around the fact they find him immensely likeable.
Beyond that though, you feel Milan are grasping at straws when they try to justify this signing. They talk about his huge sponsorship and commercial deals and his enormous followings on Facebook and Twitter. All of that is true, but most of those commercial agreements predate his sudden decline. And, as for Twitter followers, Joey Barton has plenty as well; it doesn't necessarily translate into cold, hard cash.
With Milan, as ever, when it comes to "suggestions" from above - ie decisions made, often seemingly on a whim, given the amount of other things on Berlusconi's plate - you learn to take the good with the bad. This is still a club to be feared at European level, partly because pedigree does matter and partly because there are enough individuals who can hurt you. Balotelli has been in great form since he arrived, both for Milan and for the Azzurri. And while you don't want to be fooled by another potential false dawn, he has seemed more mature and less paparazzi-prone.
The rest of the squad seem content to play for him (though a front three of Balotelli, Matri and Kaka puts a tremendous defensive onus on the midfield). And Allegri has endured so much over the past two seasons while finding a way to make things work that you feel he can squeeze performances out of the side.
When you think about it, for the past decade or so, Milan have effectively been treading water, wringing as much as they could out of their golden generation, making little tweaks hear and there to stay in the hunt. Often this was rewarded with more titles and silverware and so there was no reason to change.
However, in the past 12 months, it really did feel as if they had finally made the big decision to rip up the blueprint and start over, with youth and a more sustainable project (Financial Fair Play gave them the perfect excuse). It was overdue and it was working. And then, in the space of a few days, it all went out the window with the signings of Kaka and Matri.
It was a gamble the club did not need to take. Not now anyway.