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Ten Jose Mourinho’s worst signings

By Christopher Owuor
Monday, November 25th, 2019
Jose Mourinho.
In summary

Jose Mourinho was appointed  Tottenham Hotspur coach last week following the sacking of Mauricio Pochettino and he will be tasked with turning around their fortunes, including in making a few signings. While he has been largely successful, not all deals went well. 

1. Tal Ben Haim (Chelsea)

Kicking off the top 10 is current Maccabi Tel Aviv defender Tal Ben Haim. He is now playing for the small Israeli team as if he wasn’t part of one of the biggest clubs in the world.

Jose Mourinho signed the defender as a replacement for injured John Terry and Ricardo Carvalho during his first spell at Chelsea football club.

The 33-year-old signed a four-year deal at Stamford Bridge but did not last as he was sold to Manchester City the following year as he was not good enough to challenge Terry and Carvalho.

2. Tiago (Chelsea)

Coming in at number nine is Tiago. Let’s not blame Mourinho for Tiago being one of his worst signings.

Mourinho signed Tiago and he managed to make 34 appearances for the Blues before parting companies with the club as they were now able to acquire the services of Michael Essien.

Essien was a far better player for Chelsea considering Mourinho’s playing style at the club. Tiago was left with no choice than leave Chelsea, he signed for French club Lyon.

3. Asier del Horno (Chelsea)

Asier del Horno was the player Mourinho signed to take up the left-back position before finishing the acquisition of Ashley Cole from London rivals Arsenal.

Asier del Horno (Chelsea).

What he thought would be a first choice player didn’t go as planned as that spot was taken by the legendary Cole and del Horno became more of a transitional player at Stamford Bridge. After joining in 2005, Del Horno left the club in the summer of 2006. 

4. Jiri Jarosik (Chelsea)

Despite winning the Premier League with Mourinho at Chelsea, the Czech Republican footballer is considered as one of the Portuguese coach's worst signings.

He was a player who was brought into the team to help out in defence and midfield for title contenders Chelsea.

He managed to get himself a few appearances for the Blues but a year less after joining the Londoners, he was loaned out to Birmingham City and was then later sold to Celtic in 2006, after only spending a year at Chelsea.

5. Michael Essien (Real Madrid)

Well, his name only appears on this list after Essien was signed on loan at Real Madrid when Mourinho was a manager there. Essien reunited with the person who brought him to Chelsea but by this time the Ghanaian had lost his touch due to several injuries.

Mourinho was looking to reignite him at Real Madrid but he failed to make use of his short stint at the Bernabeu. So despite his legendary status at Chelsea, Essien became one of Mourinho’s worst signings in Madrid.

6. Mateja Kezman (Chelsea)

The Serbian striker joined Chelsea while Didier Drogba was also there so he shared the limelight with the Ivorian, who was more influential and was good in front of goal. Mourinho signed the Serb from PSV for £5.3 million.

He played for Chelsea for 24 League games and scored four goals in the process which was not good enough for a striker and when you have a player like Drogba as your competition, you wouldn’t last at the club.

7. Fabio Coentrao (Real Madrid)

When Mourinho signed Fabio Coentrao, everyone thought he was the right person for Real Madrid. He was a player who can play as a left-back and as a winger for the Los Blancos.

Fabio Coentrao (Real Madrid).

After Mourinho left Real Madrid, Coentrao couldn’t continue to be part of the first team as he faced a number of injuries and was shipped out on loan to Sporting Lisbon. 

8. Shaun Wright-Phillips (Chelsea)

Another of Mourinho’s worst signings is English footballer Shawn Wright-Phillips who is currently playing in the Major League Soccer for New York Red Bulls.

Shaun Wright-Phillips (Chelsea).

Wright-Philips joined Chelsea for a fee of £22 million from Manchester City, this transfer fee was so ridiculous as the player ended up to be just a backup.

After three years at the club, he left to rejoin old club City where he also fell out of favour and ended up becoming a reserve player for Queens Park Rangers.

9. Juan Cuadrado (Chelsea)

Mourinho acquired the services of the Colombian in the January transfer window of 2015 from Fiorentina and only spent half a season with the Blues before going on loan to Serie A side Juventus as he failed to break into the first team at Chelsea.

What Mourinho had planned for the Colombian winger didn’t actually work out as he thought he might use the midfielder for his pace to break on the counter-attacks.

But he failed to produce anything at Chelsea and after multiple underwhelming performances for the first team, Cuadrado found himself on the bench more often than not. 

10. Andriy Shevchenko (Chelsea)

The worst Mourinho signing is former Ukraine striker Andriy Shevchenko. Rather this was not the signing of Mourinho but Chelsea owner Roman Abramovich after the purchase of the club but it’s up to the manager to see if he can fit into the squad or not.

Well, when Shevchenko joined Chelsea, he didn’t look like a player who was once a Ballon D’or nominee and won the prestigious award, he never played the same when he was wearing the Chelsea blue shirt.