So, the other day, I was just minding my own business, scrolling through some footy news, and then boom – this talk about Allegri maybe going back to Milan. My first thought? Honestly, it was a bit of an “Oh, here we go again” moment. You know that feeling, right?

It really got me thinking, this whole idea of managers returning to their old clubs. So, I decided to do my own little “practice,” my own kind of dig into it. No fancy analytics or insider info, just me, my memories of how things went down the first time, and a good old think.
I remember Allegri’s first stint at Milan, of course. We got that Scudetto, which felt massive at the time. Some good days, definitely. But then, if I’m being honest, things sort of went a bit stale, didn’t they? The football wasn’t exactly setting the world on fire towards the end, and there were grumbles. Plenty of them.
So, my little process, my “practice” if you will, went something like this:
- First, I tried to properly remember the good stuff. That initial high, winning the league. The feeling of being on top.
- Then, I made myself think about the other side. The boring games, the fan frustration, how it all unravelled. You gotta look at both sides, right?
- And the biggest question that kept popping up: why now? What’s the thinking? Is it just a case of “better the devil you know”?
It’s a funny business, football. It’s like when you bump into an old friend you haven’t seen in ages and you think, “Hey, maybe we should hang out like the old days!” Sometimes it’s great, other times you quickly remember why you drifted apart. Not saying it’s exactly the same here, but that thought did cross my mind.
My take on all this rumbling
I’ve been watching this game for a long, long time. Seen managers come, go, and sometimes, come back again. My “practice” here, my way of figuring things out, it’s usually just me trying to connect the dots based on what I’ve seen before. When I heard “Allegri al Milan,” my brain just kicked into this mode automatically.

I actually sat down and tried to piece together the narrative. Pulled up some old feelings, dusted off some old opinions. It’s a bit like being a detective in your own mind. What really happened? Why did it end? What could be different now?
Then I thought about his recent spell at Juventus. Similar kind of story, wasn’t it? Some trophies, sure, but then that familiar feeling of things getting a bit… stuck. A bit predictable. So, the question I kept asking myself was, is that really what Milan is looking for right now? Is that the vibe they want?
This isn’t about saying Allegri is a “good” or “bad” manager. That’s kid’s stuff. It’s all about the fit, the timing, what the club actually needs at this very moment. My whole thinking process on this just reminded me how complicated these big decisions are. It’s not as simple as picking a famous name and hoping for the best.
And you know what? After all this mulling it over, going through my own little routine, I’m still not 100% sure what the “right” answer is. But that’s football for you. Full of debates, full of different views. My “practice” didn’t give me a crystal ball, but it did confirm one thing: there are rarely any easy solutions in this game. Just a lot of hope, a lot of pressure, and eventually, a decision that someone, somewhere, has to make. And we’ll all be watching, won’t we? That’s just how it goes.