Reading the Warnings in Someone Else’s Past

Is there a lesson for Arne Slot and Liverpool from a Milan manager of the 1990s?

This is a guest post from Paul Grech, the brain behind Cultured Football. It’s an excellent newsletter which highlights the best in football writing every week. Subscribe here.

Walter Zaccheroni arrived at AC Milan in the summer of 1998 without fanfare. He was 45, soft-spoken, a provincial coach who’d spent most of his career in the lower divisions before transforming Udinese into unexpected title contenders. Even so, he wasn’t the kind of coach that one thought a club of Milan’s global stature would hire.

Then again, Milan were desperate.

The previous two seasons had been chaotic after a failed experiment with Oscar Tabárez was followed by awkward reunion tours with Arrigo Sacchi and Fabio Capello that produced nothing. The club needed someone who could actually work with what they had, not chase past glories.

Zaccheroni had one key demand: bring Oliver Bierhoff from Udinese. The board agreed, even though Bierhoff was 30 and lacked the elegance of Milan’s historical strikers. But Zaccheroni didn’t need elegance; what he needed was a workhorse forward who could press, hold up play, and time late runs into the box.

The tactical setup was straightforward. Three centre-backs - Alessandro Costacurta, Paolo Maldini, and Thomas Helveg (another recruit from Udinese) - provided defensive cover. Christian Ziege and Andrés Guglielminpietro operated as attacking wing-backs. Demetrio Albertini controlled the midfield tempo while Zvonimir Boban and Leonardo drifted between lines. Up front, Bierhoff did the heavy work, supported by rotation between Andriy Shevchenko, Maurizio Ganz, and George Weah.

Milan’s football wasn’t beautiful. They sat deep, countered quickly, and scored scrappy goals. But they were remarkably consistent. While Juventus looked like inevitable champions and Lazio assembled a brilliant squad, Milan just kept accumulating points whilst shadowing the two favourites.

The title race came down to the final two matches. Juventus travelled to Perugia on a rain-soaked pitch, needing a win to secure the Scudetto. They lost 1-0. Milan beat Empoli. On the last day of the season, May 23, 1999, Milan hosted Perugia at San Siro. Bierhoff scored twice. Milan won 2-1 and claimed the title.

In the first season Zaccheroni had delivered a scudetto that nobody had expected.

That success heightened expectations. Instead of delivering on that, however, the following year began to expose Zaccheroni’s limitations. Milan finished third, which looked respectable on paper but felt unconvincing.

Opponents had figured out how to compress Milan’s wing-backs and limit Bierhoff’s influence. Injuries didn’t help, but the deeper issue was tactical stagnation. In the Champions League, Milan finished bottom of their group behind Chelsea, Hertha BSC, and Galatasaray. A humiliation for a club with Milan’s continental heritage.

Still, they stuck with Zaccheroni. He had delivered a title when no one expected one so, surely, he deserved some faith. Sadly, that proved to be unfounded. By March of the 2000/01 season, Milan had gone four matches without winning and were closer to the relegation zone than anyone wanted to admit. A draw with Atalanta that extended the winless run to five games finally forced them to face reality: Zaccheroni was never going to get Milan back to where they wanted to be. Mid-season, he was let go.

It is hard not to see some similarities with Arne Slot. He stripped back the complexity when he joined Liverpool, and made players look better through clear organization. Liverpool were consistent, rather than spectacular, and that was enough to win a merited league title.

But it is the second season that often truly tests a manager. Can he find another gear once the first has been neutralised? Zaccheroni never did. His system won him a league title, but once teams worked out how to contain it, he had no alternative approach ready. The football grew stale, solutions became repetitive, and the structural problems kept recurring.

All of that is being echoed in Slot’s second season. Yes, injuries have been severe. Yes, key players have declined. Yes, the squad needs further rebuilding. And yes, people are still struggling to get around the emotional fall-out of losing a beloved colleague. These aren’t trivial excuses. But at what point do explanations become convenient cover rather than genuine context?

Liverpool are currently producing a points-per-game return closer to that of a bottom-half side. The football has grown predictable. The same issues recur week after week without meaningful adjustment. Patterns that worked brilliantly last season now feel mechanical, easy to anticipate and easier still to defend. Much like Milan after their title win under Zaccheroni, the solutions have stopped evolving.

That did not make Zaccheroni a bad coach. It did, however, define his ceiling. Winning a league and surviving what comes next require different skills. Zaccheroni mastered the former and never solved the latter.

Slot already has his league title. That achievement is permanent proof of his quality. But titles create their own problems. They remove surprise, raise expectations, and force a manager to evolve in public.

Liverpool now face the same dilemma that Milan had to deal with three decades back. The question is no longer whether Slot can organise a side well enough to win. It is whether he can adapt quickly enough when what once worked no longer does.

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