Despite playing for AC Milan, Sheffield Wednesday free transfer has to go down as a disaster | OneFootball

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Sheffield Wednesday thought they made an astute signing back in 2016 when they bought Champions League-experienced Urby Emanuelson.

The then Dutch international was joining a side who were full of optimism after finishing in the play-offs in the previous campaign under Carlos Carvalhal.

In the season Emanuelson joined the Owls, they carried on enjoying battling it out at the top end of the table, but their big transfer arrival didn’t help towards that. They finished fourth under Carvalhal, yet couldn't achieve a Premier League return.

Why was the signing of Emanuelson considered a coup for Sheffield Wednesday?

Emanuelson began his professional career at Ajax, rising through the ranks of their youth system. He made his first-team debut for Ajax in 2005 and quickly established himself over a seven-year period he made 255 appearances, scoring 22 goals whilst getting 29 assists.

His impressive versatility meant he could play in multiple positions such as left-back, left midfielder, or central midfielder.

During his time in Holland, Emanuelson was a key part of the squad that clinched multiple pieces of silverware, but the only time they went on to win a league title he made his big move to Italy, joining AC Milan in January 2011.

His time at Milan saw him carry on his fine form and success of that season as he became an important part of the side that won the 2010/11 title so he won two league titles in one campaign.

Overall, he spent three years at the Italian side, but before he left permanently, he gained some experience in England as he had a loan spell at Fulham. In the 2013/14 season, he spent half of the year at Milan before leaving for Craven Cottage in January, and he played 13 league games for them on the right, left and in the middle of midfield.

Even though he had a poor spell at Roma it was clear to see that, when he joined Wednesday, he certainly still had the quality.

Why did it go so wrong for Emanuelson?

He joined when he was released by the Italian side Hellas Verona, and bringing him into the Championship for nothing after the success he had over the last ten years pleased fans.

However, his time at the club immediately went wrong as he was plagued with fitness injuries.

Due to this he only made his debut for the club in their last game of the season against Fulham and then he didn't feature in the play-off semi-final games against Huddersfield Town.

Emanuelson's contract was not extended and he went back to Holland joining Utrecht. After his torrid time in the Championship, he enjoyed his football again for five years, playing 96 games overall, before retiring in 2022.