Ian Ayre Reveals His Greatest Liverpool Transfer Success and Biggest Failure

For Liverpool fans, the £8.5M signing of Philippe Coutinho has been the definition of finding a bargain in the transfer market since pretty much the day the Brazilian made his way to England from Inter Milan. For many, it will be a hard transfer to top. And that many includes departing CEO Ian Ayre.

“I remember sitting in the corridors at Inter Milan for what felt like five days,” said Ayre, reflecting on his most memorable moments at Anfield following news he would be moving to 1860 Munich. “I was trying to convince them to sell Coutinho to us then jetting him back to Liverpool to sign before transfer deadline day.”

At the time, Coutinho was 20 years of age and struggling to get into the team at Inter after an early move to Europe that had seen him hyped as one of the players of his generation in Brazil—a player spoken of in the same breath as Neymar. Yet he had never seemed to fit well in Serie A.

He impressed early on in Europe under former Liverpool manager Rafa Benitez, and he impressed on loan at Espanyol under future Southampton and Tottenham boss Mauricio Pochettino. In the cagey, tactical Italian game, though, he struggled to make a regular impact and was regularly left out.

That gave Liverpool a chance to swoop, to gamble that what Coutinho had shown meant that his natural game would translate better to the Premier League than it did to Serie A. It was a gamble that has paid off in spades for the club. Ayre, though, was quick to admit that not everything works out.

“Of course, there are some signings that unfortunately don’t come off but the experience you never forget,” he added, before highlighting his biggest miss as Liverpool CEO. “Sitting in the Ukraine on the day war broke out, trying to sign Yevhen Konoplyanka which sadly never got done because of the selling club.”

Ayre and Liverpool would later run into similar difficulties trying to deal with a Ukrainian club, struggling to agree terms for Alex Teixeira, who eventually ended up moving to China in a mega deal. On the flip side, there were clear wins beyond Coutinho—like fellow Brazilian Roberto Firmino last summer.

Next season, the challenges will be far different from Ayre in the 2.Bundesliga, with fewer trips to Italy or Ukraine or Brazil. And hopefully, for whoever replaces him at Liverpool, there will be more cases like Coutinho to celebrate and fewer like Konoplyanka’s to mourn.