Whether it be in terms of whether they didn’t play as well as you expected them to be, or if they were injured/unfit all the time during their career at your club or perhaps got on bad terms quickly into their career at your club (e.g. Di Maria at Man Utd).
As a Liverpool fan, I can think of names like Aquilani, Robbie Keane, Morientes, Andy Carroll, Kewell, Litmanen, Nuri Sahin etc.
But the one that has to take the cake is Naby Keita. I was very excited when it was announced he would be joining us. He was like the 2nd best midfielder in the Bundesliga that season for Leipzig in the data and for a couple of seasons had shown a lot of great technical ability. He joins us and the rest is history. It’s not to say he didn’t have good moments with us when he had a run of games in the first team. But that was presicely the issue, getting a run of games. It was a constant cycle of spending over half his time injured and when returning, not always having his best games due to slowly returning to fitness and when he did start showing his sparkle he’d go off injured again for a while. I am not just gutted for us but gutted for him too in how it could’ve and should’ve turned out.
I was never a fan of Fat Fred, but I genuinely think he wanted the club to compete, lost his way after SBR, but I think Owen was his last throw of the dice. In hindsight it was an awful signing, Owen knew he was never going back to Liverpool, and he gave up after his 1st injury, and was only bothered about England. I think it also hurt him a lot that he missed out on winning the Champions League with Liverpool.
I remember being gutted when we signed him. He was clearly needing minutes for internationals, and dollar. But I hear you on fat boy. The FCB made him look better though. Remember that scandal about slagging off Geordie lasses when he was on some golf n prostitutes weekend?
I was actually too young then and hadn’t got into football. But my dad and his family had run ins with him previously, and never had a good word said about him. Without getting into detail, let’s just say that he was allegedly involved in some horrible stuff