Worst Chelsea Signings of all time – Biggest transfer mistakes

Hamish Woodward

Updated on:

Chelsea have been one of the biggest spenders in football since Roman Abramovic took over. However, they have had some great transfers and some horrible transfers. Big money has been spent on some of the worst signings of all time for Chelsea. Some of Chelsea’s biggest transfer mistakes have been world cup winners, Balon D’or winners, and a kid from Everton.

They have spent over a billion pounds on transfers since the Russian arrived in 2003. Some, like Eden Hazard and Cesar Azpilicueta have been some of the best Premier League transfers ever, others have been absolutely terrible.

Below I have written about five of the worst transfers Chelsea have even made in the Premier League.

Check out some of the most famous Chelsea fans in the world!

Chelsea Worst Signings

Danny Drinkwater

The midfield partnership of N’Golo Kante and Danny Drinkwater helped Leicester City miraculously win the Premier League in 2016.

The partnership was perfectly balanced and having both in your midfield seemed like a recipe for success.

So, if you’d have heard the Chelsea had bought the title winning midfield for a combined £60 million, you would probably think it was good business.

Ngolo Kante alone seemed worth that much, and he proved it in the years after. This included helping Chelsea win the Champions League and France the 2018 World Cup.

Drinkwater joined the Blues a year after Kante, but failed to have the same impact as the Frenchman.

He was signed on deadline day, even though he was not a good fit for Antonio Conte’s system. The Chelsea manager was famous for his 3-5-2 system, while Drinkwater was best suited in a midfield duo.

Because of this, Drinkwater rarely got time on the pitch with Chelsea. It appears he was a signing by the board, not by the manager. This showed, as he only played 22 times in all competition since he joined in 2017.

Unfortunately he was sent to train and play with the reserves, as well as being loaned out multiple times by Chelsea.

He is currently on loan at Reading, after spells with Burnley, Aston Villa and Turkish side Kasimpasa.

Chelsea seem to be waiting his contract out, and are resigned for ever getting a transfer fee for him.

Ross Barkley

Cominc through the ranks at Everton, a young Ross Barkley was the biggest talent since Wayne Rooney.

Barkley broke into the Everton first team at aged just 18, and soon became a fan favourite and starter in the side.

Injuries limited his involvement, but his talent was clear for all to see, especially to the higher ups at Chelsea. Barkley handed in a transfer request in the summer of 2017, and a deal with Chelsea was agreed for a £40 million transfer.

However, Barkley failed the medical, and the club and the player had an agreement to sign instead in January, for a lower price due to his contract expiring at the end of the season.

Barkley joined Chelsea for £15 million in January, and the young Englishman looked like he was going to be one of the biggest stars in the Premier League.

Sadly, injury problems blighted him just as they had at Everton. Barkley didn’t feature at all for Everton in his final season, due to a long term hamstring injury, and that would plague him when he moved to Chelsea.

He only played 54 matches in five seasons for the Blues. His 4 goals were a poultry return for such a sought-after player, and his performances never justified his £100,000 a week plus wages. He was loaned out to Aston Villa where his performances were equally poor, and looks set to leave Chelsea at the end of his contract.

With such potentially from the man from Liverpool, Ross Barkley is one of the worst Chelsea signings of all time, and a poor transfer all around.

Ross Barkley could have been an Everton legend. Check out some of Everton’s most famous fans

Abdul-Rahman Baba

What can you say about Abdul-Rahman Baba? He is a left back who was signed by Chelsea in 2015 in a £22 million pound transfer.

Thats pretty much where his Chelsea career ends. He made 15 appearances in his first season, playing pretty badly and impressing nobody.

He has spent the next 6 seasons out on loan, and surely has to be nearing the end of his Chelsea contract.

There is literally nothing else I can say. He was a nothing signing that was surely some kind of money laundering scheme by the amount Chelsea paid for him. He is definitely one of the worst Chelsea signings of all time.

Fernando Torres

Chelsea’s Spanish forward Fernando Torres celebrates with the trophy after winning the UEFA Champions League final football match between FC Bayern Muenchen and Chelsea FC on May 19, 2012 at the Fussball Arena stadium in Munich. AFP PHOTO / PATRIK STOLLARZ (Photo credit should read PATRIK STOLLARZ/AFP/GettyImages)

In January 2011, Chelsea were on the lookout for a new striker. It was long known that Chelsea owner Roman Abramovic was a huge fan of Fernando Torres, Liverpool’s Spanish striker.

Chelsea lodged a £40 million bid for Torres on the 27th January 2011, which Liverpool promptly rejected.

However, Fernando Torres handed in a transfer request, which made Liverpool scramble to replace him with just four days left of the transfer window.

Chelsea then signed the striker in a £50 million deal, the biggest fee ever paid by a Premier League club.

Liverpool used the money to sign Luis Suarez and Andy Carroll, but Chelsea were happy with their man.

Torres had just won the Euro 2008 and 2010 World Cup with Spain, and despite injuries was still considered one of the best strikers in the world. However, he would go on to be one of the worst Chelsea signings in the clubs history.

Torres at Chelsea

You would not have thought so once he set foot in Stamford Bridge. He looked out of form, out of fitness and just down right bad when playing for Chelsea.

The player who had lit up Anfield was no more, and Chelsea had bought a shadow of Fernando Torres’ former self.

He only scored one goal in his first season with Chelsea. It was clear he had rushed back from injury too quickly, and was not the player he once was.

His explosive pace had abandoned him and his confidence in his finishing ability was shot. This was most evident when, in a match against Manchester United, Torres masterfully took the ball round David de Gea and blasted the ball wide form an open goal.

After his first season, Torres was fine. He scored some important goals, but was never the main man that Chelsea paid £50 million pounds for.

He did score against Barcelona in the Champions League semi-final, but the goal was ultimately useless as Chelsea would have gone through regardless.

Overall, Fernando Torres only scored 20 times in 110 league matches, which for £50 million was pitiful.

He is one of the most disappointing transfers based on the transfer fee, and one of the worst Chelsea signings of all time.

Andriy Shevchenko

At AC Milan under Carlo Ancelotti, Andriy Shevchenko was one of the best strikers in the world. He was the main goal scorer in one of the greatest AC Milan sides of all time.

Shevchenko led the line for an AC Milan side that reached two Champions League finals, winning one. In 2003, he became the first Ukrainian to lift the trophy, as Milan beat Juventus in the final. Shevchenko scored the winning penalty, writing him into the record books at AC Milan.

He averaged more than a goal every two games at AC Milan. Messi and Ronaldo’s unreal stats have blurred the lines of top goal scorers nowadays, but back then the record was one of the best in the world.

In 208 league matches, he netted 127 crucial goals for the I Rossoneri, and a further 47 in all competitions. He was the best marksman in the world on his day, and when Chelsea came calling in 2006, other Premier League clubs quaked in their boots.

However, Shevchenko’s stay in England did not quite go as well as anyone was expecting. Especially not Chelsea.

Shevchenko at Chelsea

Shevchenko joined Chelsea in the summer of 2006. It came just a year after AC Milan’s defeat to Liverpool in the Champions League final, but he was still considered one of the best strikers in Europe.

He joined in a £30 million deal from AC Milan. This topped Michael Essien as Chelsea’s record transfer, and the expectations were high for the Ukraine striker.

Shevchenko was competing with Didier Drogba, who led the Blues to the Premier League title for the past two seasons. It was hoped that Shevchenko would surpass Drogba and become the main man at Chelsea.

His first season with Chelsea can only be described as “Sporadic”. He scored 14 times in 51 matches, which wasn’t a bad return, but for a record transfer was disappointing. He failed to displace Drogba as the starting striker in the team, and even worst Chelsea lost the Premier League title to Manchester United, for the first time in three years.

Injuries and poor form

His season was cut short due to injury, and boss Jose Mourinho hoped he would come back firing the next season.

The next season was even worse. Shevchenko spent the bulk of the season out injured, playing only 17 matches. He scored only five times for Chelsea, and made little impact as they once again finished second in the league. He was also an unsused substitute as Chelsea lost the Champions League final on penalties to Manchester United.

Andriy Shevchenko only played one more game for Chelsea, at the start of the next season. He was then loaned out to AC Milan his former club. He left on a free transfer the next season to hometown club Dynamo Kiev.

For someone with such hype, and with a such huge transfer fee, he is one of the worst transfers Chelsea ever made. The parallels with Fernando Torres are shocking, but at least Torres scored that goal against Barcelona. There is little to show for Shevchenko’s time at Chelsea, which is sad for such a superstar of world football. He is one of worst Chelsea signings in the history of the club, and a terrible transfer all round.

Privacy Policy