3) Andriy Shevchenko
For a man who scored 127 league goals in 208 appearances for Milan, Shevchenko has an unfortunate case to be remembered as the biggest transfer flop of all-time due to his horrid Chelsea career.
It was heart breaking to see one of the deadliest strikers of his generation depart the San Siro for an astonishing £40.5m to muster just nine goals in 48 league appearances.
His reputation may have taken a savage beating after his time at Stamford Bridge, but the now retired hit man deserves to be remembered for his formidable record in Italy.
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