Premier League

Chelsea’s worst XI of the 21st Century includes Shevchenko, Veron and three of Tuchel’s current squad

CHELSEA have shot to prominence since the arrival of owner Roman Abramovich shortly after the turn of the century.

The Blues have won five Premier League titles and two Champions Leagues in the last 17 years, a sensational return for the club.

Some of the biggest Chelsea flops since the turn of the century

However, they have still made seriously poor signings over the past two decades, with Simon Phillips highlighting what he believes is the worst team made up of those flops.

Goalkeeper – Kepa Arrizabalaga

It feels harsh putting Kepa in here, but you really don’t have an option purely based on how much the club spent on him and how he has now spent the last season being a firm number two choice and also losing his place in the Spain squad.

Look, he isn’t a bad keeper at all, but he has been an absolutely disastrous signing for Chelsea in a business sense. The club invested £71m on him and they will get nowhere near that fee back when they inevitably sell him either this summer or one of the next windows, because whilst Edouard Mendy is at Chelsea, Kepa is continuing not to get a look in.

It’s a sad story because he’s never complained and he’s stayed professional when called upon, you cannot doubt that. He has also suffered with confidence, but when asked to name a starting Xl with some of the worst players Kepa has to be in goal. I’m not going to stick a second or third choice keeper in here, because they are literally bought as backup options, Kepa was bought as our ‘world class’ number one stopper for many years to come, and it’s failed miserably.

Right back -Khalid Boulahrouz

Costing Chelsea £8m, but made 13 league appearances in two seasons, there was no way this guy was ever going to be a regular for Chelsea. Perhaps he was just cursed by being given the Chelsea number 9 shirt, which was entirely very odd.

Centre back – Papy Djilobodji

This guy perhaps goes down as Chelsea’s worst and most random signing of all-time. Whoever scouted him should have been sacked on the spot, the poor lad wasn’t even Championship quality let alone Premier League quality, and he left Chelsea having only played one very short appearance as a sub! Still playing though I believe in Turkey.



Centre back – Winston Bogarde

Bogarde stayed at Chelsea for four years, collecting his 40k-a-week wages but only made 12 appearances. This one was nothing short of expensive and disastrous. Bogarde is probably one of the most disliked Chelsea players of all-time to be honest, and he certainly likes to bring the drama.

Left back – Asier Del Horno

The left back cost us £8m and only had one season at the club. Famed for being sent off for hacking down Lionel Messi in the Champions league, and the rest is history, so was he!

Midfield – Tiemoue Bakayoko

Again, it feels harsh putting Bakayoko in here but you cannot ignore what another waste of money he was for Chelsea. He’s been on Chelsea’s wage bill since 2017 and as I type, he is still no closer to joining a new team on a permanent deal. 

He’s proven to be a fairly good player, but he never made it at Chelsea and never will unfortunately. This one hurt more because again, he was supposed to be the next big thing in midfield.

Midfield – Danny Drinkwater

An absolute waste of £40m and a transfer that continues to anger Chelsea fans now. It really looks like Drinkwater will be staying on our wage bill seeing out his contract and will also go down as one of the worst transfer Chelsea have ever made, behind Djilobodji. 

He isn’t a bad player, and we saw that at Leicester, but what Chelsea were doing thinking he would be good enough for a team of our calibre I have no idea.

Midfield – Juan Sebastian Veron

I remember being excited when Chelsea paid £15m to sign Veron, I always thought he was a class player and could still prove himself in the Premier League. However, it was a disaster and ended up costing Chelsea £1m per appearance for Veron, as he only had 15 appearances for us.

Forward – Marko Marin

We were sold ‘The German Messi’ dream when he arrived at the club, but unfortunately he proved that he wasn’t even worthy to tie Messi’s boots. This lad is only 32-years old and is still playing now you know, in the Saudi Arabian league! We were sold the dream, but in reality he got a measly 6 league appearances for Chelsea.

Forward – Andriy Shevchenko

Great manager, and a great striker, but just not for Chelsea. He signed for a big fee at the time, £30m, but only managed to return 9 league goals for Chelsea’s investment, which can be nothing less than disastrous. The Chelsea striker curse? Maybe.

Forward – Alvaro Morata 

Another man who was definitely hit by the Chelsea striker curse was Alvaro Morata. I felt sorry for him at times, but in the end he was one of the most frustrating players I have ever watched play for the club.

Blamed everyone and everything else other than himself, missed sitter after sitter, and cost an absolute bomb at £60m, which was a club record fee at the time. The silver lining of course is that we got £50m back for him when we eventually did sell him, but still, a disastrous spell at Chelsea for him.

Twitter: @siphillipssport

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