#1 Rafa Benitez sells Xabi Alonso for Gareth Barry
Well this one is just embarrassing in hindsight, and also a primary reason for Liverpool’s downfall post-2009.
Rafael Benitez is currently managing Newcastle United in the Championship. From winning the Champions League with Liverpool to going there in just over a decade, you don’t have to be a pundit to know that he made some bad decisions along the way- perhaps none so fatal and laughable as this one.
Xabi Alonso was brought to Merseyside by Benitez, and he was an integral part of the team that won the Champions League in Istanbul on that famous night. The Spaniard formed a deadly partnership with captain Steven Gerrard in the middle of the park and his influence in the team was unparalleled.
Despite all that, Xabi revealed in his autobiography that the manager told him he could leave the club in 2008, a year after Liverpool reached the CL Finals again.
In a move that since figures like Gerrard and Jamie Carragher have blasted and called stupid, Benitez sold Alonso to Real Madrid for £30M. The manager wanted to get some funds to finance a move for some other players, and at the top of that wish list was none other than Gareth Barry.
Now although Barry is not a bad player, selling Alonso to buy him would be like selling your Ferrari to buy a Fiat. Alonso’s departure left a gaping hole in the middle for Liverpool and the Barry deal never went through. A year after his sale, Liverpool were performing horribly and eventually Benitez left the club.
In his new book, My Story, Gerrard said: "It was clear Alonso was royalty after our first training session together in August 2004, and Rafa Benitez, who had been so clever to buy him in the first place, was equally stupid to sell him to Real Madrid five years later.
"He was, by some distance, the best central midfielder I ever played alongside.”
Alonso went on to win the World Cup and two Euros with Spain, as well as another Champions League trophy with Real Madrid and still starts for Bayern Munich. It can be said that without a doubt, this decision to sell the gifted Spaniard is the worst one made by a manager in the modern day.