Liverpool v AC Milan evokes mixed memories of defining match-ups in clubs’ legacies

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Some games define the direction of a club’s future. Liverpool’s previous Champions League matches against Milan – both finals – are in this category. The teams meet for just the third time on Wednesday night at Anfield in the competition’s group stage and the memories evoked by the match-up are mixed, to say the least.

The Miracle of Istanbul in 2005 will forever be remembered as one of the most famous nights in the history of European football. Liverpool were 3-0 down at half-time, recovered to level the score, took the game into extra time and eventually prevailed on penalties. It was a joyous night for British football that captured global attention.

The rematch two years later in Athens was Istanbul’s evil twin. Nothing about it was uplifting. Rafa Benitez and his team squandered a massive opportunity to become continental champions for the sixth time. The behaviour of some Liverpool fans was appalling and dangerous. And the 2-1 defeat was the spark for an Anfield civil war whose ramifications are still being felt.

Istanbul’s negative effects rarely get mentioned. It revitalised Liverpool’s global appeal but the downside was that many of those who missed out on the festivities in Turkey resolved never to make a similar mistake again. Athens was flooded with ticketless supporters. In Liverpool’s previous adventures in Europe, there was a general acceptance that almost everyone who made the journey to the final made it into the ground. In Greece there were no tickets floating around like in Istanbul. Those that were being offered for sale were trading at eye-watering prices. Things had changed significantly in two years.

For the clubs it was different, too. Rick Parry, Liverpool’s chief executive for both matches, noted that Uefa’s priorities were different. “The teams were no longer top of the list for hotel allocations,” he said. The emphasis had switched to give corporate interests pre-eminence.

Before the game, hordes of supporters stormed the Olympic Stadium. The chaos was worsened by a shambolic police and stewarding operation. The stands and aisles became dangerously overcrowded. Ticket-holders were denied entry and many who possessed fakes made it inside. Panicking police used tear gas and baton charges to try and restore order.

The game was played against this ugly backdrop. There was little between the teams but Benitez’s tactic of playing Dirk Kuyt alone up front meant Liverpool were toothless for much of the match although they were arguably the better side. The introduction of Peter Crouch with 12 minutes left offered a hint of what could have been and Kuyt scored a late goal. Craig Bellamy remained unused on the bench and a number of his teammates believe that the Welshman would have made a huge difference.

One of the knock-on effects of Istanbul is that it alerted foreign investors to the potential worldwide appeal of football. George Gillett, an American businessman, became interested in buying Liverpool. He could not afford it so persuaded a friend, Tom Hicks, to become involved. Three months before Athens the pair acquired Liverpool in a leveraged buyout. The debt was placed on the club. Those hoping for Roman Abramovich-style investment were disappointed. Gillett and Hicks were more concerned with taking out than putting in.

By the time the Champions League final came around, Benitez had already lost faith in Anfield’s new owners. On the day after the defeat by Milan, he went on the attack, demanding funds to keep the team competitive. It was the opening salvo in a conflict that would tear the club apart over the next three years and its consequences would be felt well into the next decade.

Fenway Sports Group (FSG), who picked up the pieces of the Gillett and Hicks era, still suffer from suspicions that they have a similar mindset to their compatriots. By 2010, when FSG took control, a culture of protest and a supporters’ union, Spirit of Shankly (SOS), had been established. SOS have been a force for good. The latent mistrust of American owners has not been so positive.

Even this summer a small but angry section of the fanbase have tried to create an “FSG Out” campaign, largely based around the owners’ refusal to spend freely in the transfer market. Benitez’s problem after Athens was that he wanted to be allowed to spend the money he had been promised and that the run to the final had generated. Instead, Gillett and Hicks broke their word and began actively taking money out of the business. The poisonous tendency to conflate FSG with their predecessors stretches back to 2007. The defeat to Milan in the Greek capital was a turning point and it took until well into the next decade to stabilise the club and begin moving forward.

Much has changed in the 14 years since the teams last met. Milan, the seven-time European champions, have not won the Champions League since. It is now a decade since their last Serie A title. Financial power has shifted away from Italy.

In 2007 Milan were No 5 on Forbes’ list of the most valuable clubs in football. By this year’s version they had fallen to 16th. Liverpool are fifth.

Wednesday’s match is unlikely to be a landmark game for either side. There is no trophy at stake. It is a clash of European aristocrats but, compared to the two previous encounters, the action at Anfield will be a low-key event. Perhaps that’s just as well for Liverpool after those epoch-defining showdowns in Istanbul and Athens.