How do you end up with Max Allegri as your top choice?

About a decade ago I took a trip to Tacoma, Washington for a corporate training retreat. We didn’t get much time to eat, but every day, I snuck out of the training and went to a local Red Robin (I’m not a strong enough man to turn down unlimited fries). Three days in a row. On the third day, having the same waiter each visit, he said to me “how did you end up coming here every day this week?”

He meant to ask, why are you ordering a grilled cheese every day for lunch but what it made me think of is “what choices does someone make in life to end up at a Tacoma Red Robin three days in a row?” Apparently, not the best choices.

My brain raced and thought.. well I took this side gig, and they flew me out and then.. and then… but in reality, he just was making conversation. I’ve always been one to go a little deeper than what I think people mean when they ask rhetorical questions like that.

But really… how the fuck do you end up with Max Allegri as the manager, years after he was run of town.. went to Juventus.. lost some CL finals.. and is now back after they had enough of the stochastic terrorism that is Allegriball?

Well, on May 8th, 1967, a man named Gerald was born. He did what most rich people do when they want to get into Harvard, became a rower and put that on his application. He then went to Goldman Sachs, where assholes go to gestate.

Sure enough, in just a few short years he was ready to suck the value from the work that other people did in order to enrich himself. As a certified non-asshole, he worked with people who you never would confuse with that sort of thing, George Steinbrenner and Jerry Jones.

Fast forward to today, and this FloridaMan is three years into running AC Milan into the ground. A process he took on gradually, of course. Year one, he opted to let the competent people run the show; those same people who turned the banter-era pile of scrap into a lean machine punching above it’s weight.

Cardinale had the sense to let that build on it’s own. After all, as a venture capitalist attaching to the host, it was his job to suck enough blood that he could grow, but not enough that he would kill his host. Otherwise..

There always was going to be a needle to thread, and there always was going to be some give and take. Cardinale, though, is functionally illiterate when it comes to the asset he purchased. Who knew the club he purchased had a long and storied history? Certainly he didn’t. Who knew they had the second most Champions League trophies? Maldini probably did.

Which is a problem. Back in the spring of 2023, after losing a Champions League semi-final, Maldini hopped on the CBS post-game show being aired across America and essentially said, we need more money..we did well…we need more to become better.

It seemed reasonable, but Cardinale, being a man who provides no inherent value himself, needed to assert dominance. So Maldini was fired, and the inmates began to run the asylum.

Nothing says stable growth like a power void, so no need for another sporting director. When he says “in it to win it” telling Bloomberg during an interview that it wouldn’t be very fun if Milan won everything every season, he meant it in the good way, not the bad way where making money is more important than the actual objective of the sport itself.

This isn’t someone who wants to win, this is someone who wants to make money. We know this. He’s tried to hide it because it’s frankly, ghoulish to take something that millions of people use to derive joy and find a way to milk out an accounting profit on the asset. But then again, this would be the guy to do it, right?

Redbird ASSET management. The club isn’t a beloved institution and calling card of an entire city. Cardinale is not a steward of said club. He’s not accountable to the fans, because of course he, in his own mind, IS the club. It exists as a line on a spreadsheet that makes it so he can enjoy the last few years his house on the beach has before it’s reclaimed by the ocean and so he can have an extra yacht to take on a spin when he’s bored of his first.

People like this always have a sense of entitlement, a sense of over-importance of their actions. A savior complex.

That’s how you can convince yourself to fire Paolo Maldini. That’s how you can appoint Zlatan Ibrahimovic, probably the least self-aware person in the club’s orbit to take over a sensitive role.

That’s how you can leave a power vacuum and not do anything about it for a full season. That’s how you can hire your 6th choice manager last summer. That’s how you can convince yourself that an algorithm created for a different sport on a different continent can do a job better than someone who was successfully doing it.

That, is how you dig a hole.