During his coaching career, he has bought or loaned 133 players with 58 of them coming in his 8 years of his English coaching career. However, even after being a transfer wizard, the Portuguese has faltered in the transfer market quite a few times. Down are some of Jose Mourinho’s biggest transfer mistakes of his coaching career in the Premier League.

5. Andriy Shevchenko

Shevchenko’s transfer fee of £30.8 million was a club record as well as a national record at the time. He started his Chelsea career on a bright note, scoring in the first game itself.

After that, he could only score 14 goals in 51 games which were a very disappointing return by his lofty standards. He was mostly anonymous for Chelsea and it was annoying to see him completely fail to adjust to the pace of the Premier League.

He was soon loaned off to Milan and in the subsequent season got sold to Kiev. After all, pairing him with the footballing beast called Drogba was something that many fans or analysts could not understand. Both of them were players of similar style.

4. Mateja Kežman

When Mourinho bought Kezman from PSV Eindhoven for a mere amount of £5.3m he was considered by many as the signing of the season. After all, the Serbian player had scored 105 goals in his 4 previous seasons making 111 appearances in the league playing for PSV.

In his previous club, his partnership with Arjen Robben caused a havoc for the rest of the Eredivisie sides. However, even the presence of his Dutch counterpart Arjen Robben at Chelsea could not help him settle at the club. He could only score 4 goals in the entire league season out of which the first goal didn’t come till December.

He was shipped off to Atletico Madrid the very next season.

3. Kevin de Bruyne

Kevin de Bruyne is often considered as one of the most complete footballers on the planet. He is also arguably the best footballer in the Premier League currently. Well, that could have been in Chelsea’s favour had Mourinho been a little patient with him during his time with Chelsea.

Though due to injuries and some weird decision making on the management’s part to play him out of position, the Belgian could not showcase his perceived potential. Although his talent was never in doubt, yet Mourinho sold him to Wolfsburg a season later for £22 million. The rest is history.