5 biggest transfer mistakes in Chelsea's history

One of the biggest and most successful clubs of the Premier League era, Chelsea have, for the most part, used the transfer market to their advantage over the past three decades.

Over the years, Chelsea have been able to bring some of the world’s best players to Stamford Bridge. But they’ve also made many mistakes when it comes to transfers.

The Blues have over-spent on big money flops, and they’ve also let players, who would go onto become Premier League legends, out of their grasp.

On that note, let's take a look at five of the biggest transfer mistakes in Chelsea’s history.

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#1 Fernando Torres – Liverpool to Chelsea (£50m) January 2011

Fernando Torres failed to live up to his £50m price tag at Chelsea.

When Chelsea decided to part with a British record fee of £50m to bring Fernando Torres from Liverpool to Stamford Bridge in January 2011, it sounded like a good idea.

‘El Nino’ had practically been a goal machine for the Reds since arriving at Anfield in the summer of 2007. His first three seasons at Liverpool saw him score 56 goals in just 79 appearances.

However, what Chelsea’s power-brokers didn’t realise was that after suffering a serious knee injury in the latter part of the 2009-10 season, Torres wasn’t quite the same player he once was.

On his arrival at Stamford Bridge, not only had the Spaniard lost a yard of pace, but he also looked like he had the weight of the world on his shoulders. It took him 14 games to open his goal account for Chelsea, and that strike turned out to be his only one in his first campaign for the Blues.

His record improved in 2011-12, as he scored 11 goals in all competitions, but he also went on a 24-match barren run in the same campaign.

By the 2012-13 season, despite scoring 22 goals, Torres was largely regarded as one of the Premier League’s all-time most expensive flops. And in 2014, he departed Chelsea for Milan, having scored just 20 Premier League goals for the Blues in 110 appearances.

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#2 Mohamed Salah – Chelsea to Roma (£13.5m) August 2016

Mohamed Salah went onto become a Premier League legend, but only after being sold by Chelsea.

Since joining Liverpool in the summer of 2017, Mohamed Salah has become a Premier League legend.

The Egyptian striker has scored a phenomenal 90 goals in 135 league appearances for the Reds, winning the Premier League Golden Boot twice.

He has helped them to two Champions League finals – winning the 2019 edition – and in 2019-20, played a huge part in Liverpool capturing their first Premier League title. Incredibly though, none of this would’ve been possible had Chelsea fully recognised his talent a few years ago.

Salah first came to prominence in the eyes of Premier League fans in the 2012-13 season, when he scored Europa League goals for Basel against both Tottenham Hotspur and Chelsea, helping them to the competition’s semi-finals.

Liverpool were actually linked with a move for Salah at that stage, but instead, he moved to Chelsea in January 2014 for a fee of £11m. Quite why the Blues chose to sign the Egyptian remains a mystery, as they already had a host of wide forwards at the time, including Eden Hazard, Oscar and Willian.

Unsurprisingly, Salah struggled to force his way into Chelsea’s starting XI and made just 11 appearances in all competitions during his first half-season at the club, most of them off the bench.

The 2014-15 season didn’t see him fare any better, and after appearing in just three Premier League games, he was sent on loan to Serie A side Fiorentina.

Salah scored six goals in 16 games for the Italian side, which was enough to impress AS Roma – who took the Egyptian on loan in 2015-16 and signed him permanently for just £13.5m.

After scoring 29 goals in just 65 appearances for Roma, Liverpool made their move, and the rest is history.

Given that Salah is likely worth well over £100m at this point, it’s safe to say that Chelsea made a major error with their treatment of a player who would end up becoming a world-class performer.

#3 Andriy Shevchenko – AC Milan to Chelsea (£30.8m), May 2006

Andriy Shevchenko failed to produce his best form at Chelsea.

For the best part of a decade, Andriy Shevchenko was renowned as one of Europe’s most feared strikers. The Ukrainian plundered goals against practically any side he faced, helping both Dynamo Kyiv and AC Milan to massive success in the late 1990s and early 2000s.

By the summer of 2006, however, at the age of 30 and with plenty of miles behind him, Shevchenko had begun to slow down somewhat. That made it all the more surprising when Chelsea parted with over £30m to bring him to Stamford Bridge, despite boss Jose Mourinho seemingly not really wanting him.

Fans immediately suspected Shevchenko’s signing was a vanity project from owner Roman Abramovich, and results on the pitch appeared to back that theory up.

Shevchenko just couldn’t produce his best form at Stamford Bridge, ending his debut season with just four Premier League goals to his name.

The 2007-08 season saw him fare no better despite Mourinho’s departure midway through, as the Ukrainian scored just eight goals in all competitions. And by the time 2008-09 rolled around, it came as no surprise to see him sent back to AC Milan on loan.

When that loan spell ended, Shevchenko was still surplus to requirements at Stamford Bridge and ended up moving back to Dynamo Kyiv on a free transfer.

To call his signing an expensive mistake by Chelsea would be an understatement.

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#4 Kevin De Bruyne – Chelsea to Wolfsburg (£18m), January 2014

Kevin De Bruyne was simply given no chance to succeed at Chelsea.

Younger Chelsea fans might dream of a Blues side including Mohamed Salah and Kevin De Bruyne, but incredibly, that team could’ve been a reality had serious mistakes not been made.

The Belgian assist king – who has won seven major trophies with Manchester City, including two Premier League titles, had a very brief stint with Chelsea in the 2013-14 season.

However, he was never given a fair chance to succeed and ended up leaving Stamford Bridge for just £18m after making only a handful of appearances.

De Bruyne was signed by Chelsea from Genk in January 2012, but part of the agreement meant he remained in Belgium toll the end of the season. And when the 2012-13 campaign came around, the midfielder became part of Chelsea’s infamous 'loan army', moving to Werder Bremen for the season.

De Bruyne did well in Germany, scoring ten goals and registering nine assists, but evidently, it wasn’t enough to convince Chelsea of his talent.

He was given just nine games – three in the Premier League to prove himself at Stamford Bridge before he was sold to Wolfsburg midway through the 2013-14 campaign.

From there, De Bruyne instantly proved his class by performing remarkably for the German side. After scoring ten goals and registering 20 assists in 2014-15, Manchester City parted with £55m to bring him to the Etihad.

Every Premier League fan knows what has happened from there. Seven years after selling him, the treatment of De Bruyne must go down as one of Chelsea’s biggest transfer blunders.

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#5 Danny Drinkwater – Leicester City to Chelsea (£35m), September 2017

Danny Drinkwater's move to Chelsea has turned out to be a disaster for all parties.

Chelsea’s signing of midfielder Danny Drinkwater was always a head-scratcher, with many fans expecting to see him end up on a list like this from day one. And unfortunately for Drinkwater, his career at Stamford Bridge has basically proven his doubters correct.

The midfielder had performed tremendously for Leicester City in their 2015-16 Premier League title-winning campaign. If he had moved to a bigger club that summer, it probably would’ve been understandable.

But Drinkwater remained at the King Power Stadium for the 2016-17 season and – like Leicester City– his performance level dipped pretty dramatically.

That’s why it was such a surprise to see Chelsea decide to part with £35m to bring him to Stamford Bridge, despite not really needing to add a midfielder in what was already a top-heavy squad.

It came as no surprise to see Drinkwater make just 12 Premier League appearances for the Blues in the 2017-18 campaign. But nobody could really have expected things to get even worse for him.

Drinkwater failed to make a single competitive appearance for Chelsea during the 2018-19 campaign, as he was frozen out entirely by Maurizio Sarri. And loan moves to Burnley and Aston Villa in the 2019-20 season were disastrous too.

In the first, he made just two appearances, as he spent most of the time injured after becoming involved in a drunken nightclub brawl. And while he doubled that number with Villa, his time there ended in disgrace after he headbutted teammate Diogo Jota during a training session.

Drinkwater is currently on loan with Turkish side Kasimpasa, but at the time of writing, he’s made just three appearances for them. Even by Chelsea’s standards, the signing of the former Leicester City midfielder stands as a truly colossal mistake.