#3 Gabriele Ambrosetti
Touted as the Italian Ryan Giggs, Ambrosetti signed for Chelsea with a lot of pomp back in 1999. Perhaps, manager Gianluca Vialli meant that they both played as left-wingers, as that’s where the comparison ended. While Giggs was the core part of the dominant Manchester United attack during the ‘90s, his Italian version barely managed to trouble defences, when at his very best.
Signed for £3.5 million from Vicenza, he was a huge flop at Stamford Bridge and made only 23 appearances in his first season before being shipped out on loan. Chelsea fans obviously expected a lot but were later disappointed by the Italian’s performance.
The Italian was an average winger and stood out during his spells with decent teams all over Italy. He was, simply put, not good enough for either the Premier League or the Blues and was gone permanently in 2003 with fans wondering why he was ever signed for £3.5 million.
What actually prompted Vialli to bring the Italian to the club was a Cup-Winner’s quarter-final game where Amberosetti tore through the Chelsea back-four and showed what he could do. Unfortunately for Vialli, the left-winger could never recapture that performance at Stamford Bridge and other than his goal in the Champions League, Ambrosetti never lived up to his price tag.