Whenever Liverpool have met AC Milan, there has been a tremor in the football universe.
Given that they have 13 European Cup wins between them, it is curious the European aristocrats have faced each other only twice, both in the final. The aftershocks of those games still linger.
For many Anfield historians, nothing will eclipse 2005, commonly referred to as “The Miracle of Istanbul”, when Rafael Benítez’s flawed side overturned a three-goal deficit to defeat Carlo Ancelotti’s team of football gods.
For Milan, the scars may never fully heal, but vengeance was swift as they secured a 2-1 win in Athens in 2007 thanks to Filippo Inzaghi’s double. The second final was more memorable on Merseyside for the considerable debris after defeat. Milan’s win effectively precipitated a revolution at Liverpool, as it inspired Benítez to deliver the first of what would be many explosive press conferences in the subsequent months and years, ultimately leading to Anfield regime change.
In the hours after the 2007 final, Benítez wandered around the team’s hotel grounds considering his post-match assessment with his closest confidants. He decided it was the right moment to publicly query the motivations of Liverpool’s recently installed owners, George Gillett Jr and Tom Hicks who – despite Liverpool’s progress to the final – Benítez suspected were big on promises but short on action. What followed in front of the assembled media was Liverpool’s “Battle of Bull Run”, the starting pistol in the Anfield civil war of 2007-2010.
“I want things to be done,” said Benítez on the morning of May 24, 2007. “If we don’t change things right now and understand how crucial this moment is, we will waste another one or two months. They say they will back me. I’m tired of talking, talking. We talk and talk, but we never finish.”
The incendiary remarks blew apart the mirage that the new owners would usher in the prolonged period of stability that Liverpool needed to challenge Manchester United and Chelsea.
Although there would be occasional periods of truce, especially the next summer when Fernando Torres was among the signings, the Kop was mobilised upon realising the money Hicks and Gillett used to buy the club and subsequently invest in the team arrived courtesy of risky, high-interest loans and re-financing agreements which relied on Champions League football.
They defaulted on these loans when Liverpool dropped out of the top four three years later, risking the club falling into administration. With Fenway Sports Group waiting to pounce upon a depressed institution, the rest is history.
The landscape is much different for AC Milan and Liverpool ahead of Wednesday night’s meeting. In 2005, the Italians were still established among the elite, while Liverpool were trying to muscle their way back to the top table. Now the roles are reversed, the Rossoneri advancing in the process of restoring the reputation that made them one of the most feared teams in world football. The seven-time winners are back in the Champions League for the first time since 2013-14 and – unlike in those final meetings – must be considered underdogs ahead of their Anfield trip.
Although Liverpool’s current owner, FSG, still takes its fair share of flak – witness the almost hysterical social-media responses to the failure to buy a couple of back-up players this summer – the post-2007 memories are a reminder of how dysfunctional Liverpool were when they and AC Milan last met.
No other game in Europe this season will have more heritage to live up to. “If you were to think about any kind of European battle, then Liverpool-Milan is a must-watch. It is one you want to see,” said Jürgen Klopp, the Liverpool manager, who is never shy of hyping up the most attractive games. “AC Milan … a big history in the best moment for years? That is proper Champions League.”
As the Champions League anthem plays at Anfield, somewhere else on Merseyside there can be no one whose emotions are more conflicted than that of Benítez, – who quirkily replaced his managerial adversary of 2005 and 2007, Ancelotti, at Everton.
His loyalties have switched to Goodison now, but when seeing the collision between those European titans, , he will surely not be able to resist reflecting upon his place in the fixture’s lavish history.
Team details (probable)
Liverpool 4-3-3: Alisson; Robertson; Matip, Van Dijk, Alexander-Arnold; Fabinho, Henderson, Keita; Mane, Jota, Salah.
AC Milan 4-2-3-1: Maignan; Calabria, Tomori, Romagnoli, Hernandez; Tonali, Kessie; Florenzi, Diaz, Leao; Rebic.