Name: Massimo Taibi
Signed: August 1999 from Venezia (£4.5 million)
Then: Injuries to Bosnich and back-up keeper Raimond van der Gouw forced Manchester United back into the transfer market for another keeper. This time, Alex Ferguson decided to splash the cash. Italian keeper Massimo Taibi was somewhat of an unknown outside his native land. However, Ferguson assured fans that he was the real deal and decided to part with £4.5 million for his services. All the fan’s dreams seemed to have come true as Taibi picked up the Man of the Match award in his debut against Liverpool. However, the dream was short lived. Just a week later, Taibi made potentially one of the biggest howlers in Premier League history. Southampton’s talisman Matt Le Tissier hit what could only be described as a “pea roller” towards the goal. Despite having all the time in the world to bend down and pick up Le Tissier’s shot, Taibi somehow left the ball squirm under his body and into his net. Weeks later, United were on the end of a 5-0 drubbing by Chelsea and Taibi’s time with the club was over.
Now: Taibi was voted by Manchester United fans as one of the worst signings in their history. The goalkeeper only ever made four appearances for the club and, in 2000, was shipped back to his native Italy. He steadily rebuilt his career with Reggina, Atalanta and Torino before retiring at Ascoli in 2009. Taibi has since blamed a registration problem and family issues for his lack of games at United. He laments his reputation and is thought to be living a quiet life out of the limelight.