#2 Andy Carroll
To be fair to Kenny Dalglish, at the time, the signing of Andy Carroll didn’t seem completely absurd. The Newcastle striker was seen as a more powerful and clinical Peter Crouch. He was seen as a target man that possesses technique and aerial presence.
However, after costing the Reds £35m, the fans were expecting the big man to land on his feet instantly, which injuries didn't allow him to do.
He was bought in January, but his fitness only allowed him to debut in March. On top of that, he only scored 2 goals for the remainder of that season, the next season, he played 35 times and scored 4 goals. These figures wouldn’t even be deemed acceptable for a relegation-battling side.
Apart from his dire performances, Carroll offered Liverpool nothing, he didn’t score enough goals, he didn’t create chances for others and off the pitch, his marketability didn’t recoup his £35m price tag.