Andriy Shevchenko was already a legend at AC Milan by aged 29, but the drive for a new challenge in 2005 cost him his worldwide reputation.
One-hundred-and-fifty-six goals in 296 appearances secured his spot as Milan’s second all-time top goalscorer after seven years at the club, and Jose Mourinho was keen for him to replicate his form in the Premier League. A deal worth £30.8m was struck and Shevchenko was handed the number seven shirt he wore at his last club.
His form didn’t continue though, with the Ukrainian scoring just 14 goals in 51 games during a 2006/07 season ultimately cut short by a hernia operation. Didier Drogba’s quality was a major stumbling block for Shevchenko during that season too, with the Ivorian scoring 33 goals in all competitions and cementing himself as the club’s main frontman.
The arrival of Avram Grant the following season spelt trouble for Shevchenko, but his own injuries were also a barrier to consolidating a successful season at the Bridge. A good run of form around Christmas was short-lived, and he ended the season with just five goals in 17 games.
Chelsea’s next manager Luiz Felipe Scolari didn’t take to him either, so his former club Milan offered him the lifeline of a loan deal which the 32-year-old duly took. Just two goals in 26 appearances saw him return to Chelsea for the final year of his contract where Ancelotti didn’t even entertain the prospect of including him in is plans for the 2009/10 season.
Shevchenko returned to his former club Dynamo Kyiv as the greatest player to ever come from Ukraine, but he could have consolidated his position as one of the greatest strikers in European football if he’d have stayed in Milan.
He didn’t have unfinished business in Italy and it was probably the right time to challenge himself in a new league at aged 29, but the Ukrainian wasn’t up to that challenge and his legacy certainly suffered because of it.