1: Jamie Robson
Lincoln City league record: 39 appearances, 0 goals.
Jamie Robson was not the worst footballer on this list, but this is a ranking of transfers rather than players. Lincoln City paid a six-figure sum to sign him from Dundee United at a time when such fees were still unusual for the club. The deal attracted attention in Scotland because Robson was an established Scottish Premiership left-back who had even scored against Rangers. City had enjoyed a strong succession of players in that position, including Harry Toffolo and Tayo Edun, and Robson was expected to continue the pattern.
The intention was clear: sign a proven top-flight player, help him excel in League One and eventually sell him to a Championship or perhaps even Premier League club. Instead, it became apparent that Robson was not ideally suited to the physical intensity of the English third tier. He was comfortable on the ball and possessed a decent touch, so there were spells in which he looked perfectly capable, but City needed far more impact from such an expensive signing. After 39 league appearances without a goal, he was sold to Forest Green Rovers rather than moved up the divisions for a profit. His subsequent career took him between League Two and the National League, underlining how badly the original plan had missed its target.
Was Charles Vernam one of the worst transfers – or one of the most mishandled? I don’t get to see many matches these days, but I saw him play at Southampton in a League Cup match in 2022 and he was the only Imp who stepped up in class and caused the opposition any problems.