The 5 worst signings in Chelsea's history

Prior to this summer’s transfer ban, Chelsea have traditionally been one of the bigger spending clubs in the Premier League; even before billionaire Roman Abramovich bought the London-based side in 2003, they were willing to spend big money on world-renowned players.

Of course, while the Blues have made plenty of signings who worked out greatly – Frank Lampard, Didier Drogba and Eden Hazard to name three – they’ve also had a lot of misses in the transfer market too, often spending huge fees on players who simply didn’t work out at the club.

Here are the 5 worst signings in Chelsea’s history – with a handful of honourable mentions.

Honourable Mentions

Radamel Falcao's loan move to Chelsea flopped badly

#1 Radamel Falcao

Colombia’s Radamel Falcao was once one of the world’s most feared strikers, as he plundered a crazy amount of goals for Porto and Atletico Madrid before making a big-money move to Monaco in 2013. But a serious knee injury derailed his career there and a loan move to Manchester United in the 2015/16 season failed miserably.

That’s why it was a massive shock when Chelsea decided to take him on loan for 2016/17, and while there was no transfer fee paid, they did pick up his eye-watering wages of around £140,000 per week. Falcao went on to make just 12 appearances for the Blues and scored just 1 goal, making his move an unmitigated disaster.

#2 Papy Djilobodji

Senegal’s Papy Djilobodji was always a strange signing for Chelsea; the Blues paid Nantes somewhere between £2.7m and £4m for the defender in 2015, but bizarrely, as soon as he’d signed then-boss Jose Mourinho admitted he’d never heard of the player.

Evidently he wasn’t convinced by his talents either, as just one day later he was left out of the Blues’ Champions League squad, and after making his debut as a substitute in an EFL Cup match with Walsall – in added time – he would never play for Chelsea again, as he moved to Werder Bremen on loan just months later before making a permanent move to Sunderland the following summer.

#3 Juan Sebastian Veron

Manchester United broke the British transfer record to bring Juan Sebastian Veron to Old Trafford from Lazio in 2001, paying £28m for the Argentine midfielder. It quickly became clear that his style simply wasn’t suited to the Premier League, though, and he was largely labelled as a flop.

Chelsea surprisingly decided to part with £15m to bring him to Stamford Bridge two seasons later as Roman Abramovich bought the club, but Veron’s time at Chelsea was equally underwhelming; he made just 14 appearances at the club due to injuries and struggles to fit in, and quickly moved back to Italy one season later.

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#5 Juan Cuadrado

Juan Cuadrado's time at Chelsea was brief and largely pointless

Colombian forward Juan Cuadrado was signed by Chelsea on the final day of 2015’s winter transfer window, and not only did the Blues pay Fiorentina somewhere around £23.3m for him, but they also sent Mohamed Salah the other way on a loan deal. To say that the fee didn’t represent money well spent would be an understatement.

It wasn’t that Cuadrado was bad per se during his time at Stamford Bridge; it was more that he was simply never given a proper opportunity to display his skills. He made his debut from the bench just days after signing and was awarded his first start just days after that, but despite boss Jose Mourinho responding to criticism of the player by stating that the Colombian simply needed time to settle in, evidently, the Portuguese didn’t feel he was worth the hassle.

Cuadrado made just 12 league appearances for the Blues that season, with 8 of them coming from the bench, totalling just 312 minutes of action. He failed to score a single goal or register a single assist, and when Chelsea signed Pedro from Barcelona the following summer, the writing was on the wall and the Colombian was quickly shunted away to Juventus on a loan deal, which was made permanent a season later for a fee of €20m, meaning the Blues likely made a loss on the player too.

#4 Fernando Torres

Fernando Torres' name remains synonymous with being a big-money flop

Striker Fernando Torres often tops lists of the worst Chelsea signings ever, largely because the Blues paid a ludicrous fee for him – a British record of £50m in January 2011 – and he simply didn’t live up to the lofty standards he’d set himself at Liverpool. But was the Spaniard really that bad? Well, yes, but it’s definitely arguable that the Blues have made a couple of worse signings.

Torres’ debut for Chelsea actually came against the club he’d moved from – Liverpool – but the match ended in a loss and he failed to find the back of the net. That set off a long drought – 14 matches to be exact - and it took another three months for him to score his first goal for the Blues in a game against West Ham. Unfortunately, it would be his only goal of the season.

2011/12 proved to be a slightly better season for him; he scored 11 goals across all competitions including a famous last-minute goal against Barcelona in the Champions League semi-final – the goal that sent Chelsea to the final, which they went onto win – but at times he appeared to have lost his finishing ability altogether and even went on a run of 24 games without a goal.

Torres did manage to score more goals in 2012/13 – a total of 22 in all competitions – but by that stage, he’d already garnered a reputation as a big-money flop that he simply couldn’t shake off, and in 2014 he was sent to AC Milan on loan and never returned to Stamford Bridge. Almost a decade on his name remains synonymous with money wasted.

#3 Tiemoue Bakayoko

Tiemoue Bakayoko's time at Chelsea was a total disaster

The expensive signing of Tiemoue Bakayoko in the summer of 2017 taught Chelsea a valuable lesson; it’s probably not a good idea to throw a huge fee – somewhere in the realm of £40m – at a player who realistically had just one good season under his belt, before which he’d come under criticism for his attitude and demeanour in training.

Bakayoko had genuinely been outstanding for Monaco during their famous 2016/17 season; a tough-tackling midfielder, he helped them to win Ligue 1 as well as make a surprising run to the semi-finals of the Champions League, but to say Chelsea never saw the best of him would be a total understatement.

The Frenchman arrived and immediately went into the Blues’ first-team under Antonio Conte, but struggled from the off, seemingly struggling with the pace and intensity of the Premier League. Bakayoko seemed to lose the ball more often than he was able to complete passes, and by the midway point of the season, it felt like the fans had turned on him.

The nadir for Bakayoko came in a February 2018 match with Watford; the Frenchman was sent off for two bookable offences inside just 30 minutes in a simply ludicrous showing, and the Blues went on to lose 4-1. Upon returning, his performances still didn’t improve, and it came as no surprise when he was sent on loan to AC Milan at the beginning of the 2018/19 season – where his struggles continued until he moved back to Monaco in the summer of 2019.

#2 Andriy Shevchenko

Andriy Shevchenko's reputation took a major hit during his time at Chelsea

Ukrainian hitman Andriy Shevchenko came to Chelsea with a reputation as one of the world’s greatest strikers, but unfortunately, he’d gained that reputation largely in the years prior to 2006. By that point, Shevchenko was 30 years old and appeared to be slightly past his prime. But that didn’t stop Roman Abramovich parting with £30.8m for him, handing him to boss Jose Mourinho who didn’t seem too enthusiastic about the new signing.

Shevchenko was given a fair chance in the Premier League – 22 starts in his debut season – but he never looked like the player who had once terrorised defences all over Europe, and he ended 2006/07 with just 4 league goals to his name and quickly developed a reputation as a big-money flop.

Despite some rumours around his future, 2007/08 saw Shevchenko remain at Stamford Bridge, but he was still unable to regain his form; 5 goals in 17 league matches and a further 4 goals in other competitions was his return for the season, nowhere close to the 34 in 51 games he’d scored for Milan in 2000/01.

When 2008/09 began, new Chelsea boss Phil Scolari decided Shevchenko was surplus to requirements and sent him back on loan to AC Milan for a season – and while he did return to Stamford Bridge for the start of 2009/10, he quickly moved to his original haunt of Dynamo Kyiv before the summer’s transfer window closed, bringing an end to a truly terrible stint in London.

#1 Adrian Mutu

Adrian Mutu's unprofessional behaviour at Chelsea makes him their worst ever signing

The likes of Shevchenko and Torres might’ve cost Chelsea more money than Romanian striker Adrian Mutu – who arrived at Stamford Bridge in the summer of 2003 from Parma for a fee of £15.8m – but no other Blues signing can match Mutu for sheer unprofessionalism during his time at the club. Simply put, the way his Chelsea career ended makes him by far their worst ever signing.

Things actually started well enough for the Romanian; as one of Roman Abramovich’s first-ever signings, the pressure was on for him to succeed and he started off quickly, scoring 4 goals in his opening 3 games including a winner against Leicester and a brace against Tottenham. 10 goals in 36 appearances across all competitions in 2003/04 wasn’t the best return, but it did seem like the best was yet to come from the striker.

That was proven wildly wrong in his next season, though. Mutu fell out with new boss Jose Mourinho almost immediately, accusing the Portuguese of lying that he was injured in order to prevent him from playing for Romania in a World Cup qualifier. Shortly after, his Chelsea career came to an abrupt end when he tested positive for cocaine – and was subsequently banned from football for 7 months.

The issue caused such a scandal that Chelsea ended up firing the Romanian – who moved back to Italy with Juventus – and eventually decided to take him to court for breach of contract following the positive test.

After years of legal proceedings, Mutu was forced to pay Chelsea £17m. The money recouped his transfer fee but still doesn’t change the fact that due to his unprofessional behaviour, he remains the Blues’ worst-ever signing.