Werner, Havertz, Kepa: Chelsea's transfer flop XI of the Roman Abramovich era

Chelsea's Timo Werner

The Roman Abramovich era has brought Chelsea a level of success that far outstrips anything that preceded his arrival. 

It's been a revolutionary period not only for the club but also the Premier League, with his arrival representing the first of an injection of fresh, foreign investment that has since transformed the landscape of English football. 

But the ensuing tidal wave of multi-million pound transfers has not been without its pitfalls. 

The Russian oligarch has invested billions of pounds into Chelsea on countless new players in a bid to transform the club into an internationally recognised behemoth, but he's made his fair share of mistakes along the way. 

Following a lengthy transfer ban for the west London outfit which prevented Abramovich from embarking on his annual shopping spree, he returned to the market with a renewed sense of vigour in 2020 as he sought to quench his thirst for an extravagant spending spree.

With the exception of Thiago Silva, though, Frank Lampard has failed to extract the best form out of any of his big-name summer signings.

Timo Werner's shortcomings in front of goal have been well documented, and his tepid performance in Chelsea's 3-1 defeat against Manchester City on Sunday got us thinking about some of the biggest flops in the history of the club. 

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Federico Fazio - quiz

Can you name this completely forgettable former Premier League player?

With that in mind, GIVEMESPORT have created an XI containing some of the biggest transfer flops of the Abramovich era. 

By taking into account both the size of the transfer fee and the player's respective impact at Stamford Bridge, we've detailed our selection below. 

Abramovich has forked out £373.1m on this collection of flops. 

Take a look at who makes the XI below...

Goalkeeper: Kepa Arrizabalaga (£71m

Kepa Chelsea

It's rare that a goalkeeper is the most expensive player in any side, so the fact Kepa earns that tag within an XI of transfer flops attests to just how disastrous his Chelsea career has been. 

Signed for a world-record fee of £71m to replace Thibaut Courtois, Kepa has created more problems than he's solved at Chelsea, and the recent signing of Edouard Mendy has left him in no man's land two-and-a-half years after he joined from Athletic Bilbao. 

The Spaniard will be infamously remembered for his refusal to be substituted during Chelsea's 2019 Carabao Cup final clash with Manchester City at Wembley as Maurizio Sarri attempted to replace him with penalty specialist Willy Caballero. 

Right-back: Davide Zappacosta (£23m


Davide Zappacosta was signed in the summer after Antonio Conte led Chelsea to the title with his revered 3-4-2-1 formation. 

The Italian's propensity to get forward and familiarity with a wing-back role suggested he would be an excellent addition to the squad, but he struggled for form during his first two years in the capital and has since returned to his home country in loan spells with AS Roma and now Genoa. 

At £23m Chelsea were expecting much more.

Centre-back: Khalid Boulahrouz (£6m)

Khalid Boulahrouz did not set Chelsea back an alarming amount of money and with good reason: he simply was never up to the standard required.

The Dutch defender made just 10 Premier League starts and moved to Stuttgart on a permanent deal just two years later.

Centre-back: Papy Djilobodji (£2.7m)


Another relatively cheap inclusion shows that Chelsea have not been overly wasteful in their pursuit of central defensive talent. 

Papy Djilobodji is the cheapest player in this XI, and despite making just one appearance for the club, he was eventually sold to Sunderland for a profit one year later. 

That he failed to cement his place in the Black Cats' starting XI in the year of their relegation speaks volumes about how ill-equipped he was for Premier League football.

Left-back: Abdul Rahman Baba (£23.4m)

At this point you're probably wondering exactly who Abdul Rahman Baba is, which explains why he's our inclusion at left-back. 

Yuri Zhirkov and Asier Del Horno were notable candidates for this position, but at £23.4m Baba has proven to be an incredible blunder from the club's transfer honchos. 

Since signing for Chelsea the Ghana international has made 23 appearances and spent time on loan at three different clubs - Schalke, Stade Reims and RCD Mallorca. 

Now back at his parent club, Baba is firmly on the fringes of the squad and doesn't look likely to emerge from first-team exile anytime soon. 

Central-defensive-midfield: Tiemoue Bakayoko (£40m)


A player who promised so much and delivered so little. 

Having starred in AS Monaco's unexpected run to the Champions League semi-final in the 2016/17 season, which included knockout stage victories over Manchester City and Borussia Dortmund, Tiemoue Bakayoko appeared to boast a repertoire befitting of a first-class midfield enforcer. 

It rapidly became apparent, however, that Chelsea had been hoodwinked. 

The Frenchman stumbled from one disaster to another and his on-field demise took place amid a backdrop of relentless criticism from Chelsea fans on social media.

He eventually faded onto the periphery of the squad and has since embarked on loan spells with AC Milan, his former club Monaco and now Napoli. 

Central-defensive-midfield: Danny Drinkwater (£35m)

Sitting alongside Bakayoko in the double-pivot is an epitome of a deadline-day panic buy.

If any club need a reason to resist the temptation to sanction a last-gasp, ill-thought out punt at the eleventh hour, Drinkwater is your man.

Drinkwater has proven to be an incredibly costly mistake since signing on deadline day of the 2017 summer window, making just five Premier League starts thus far. 

As one of the stars of Leicester City's stunning 2015/16 title win, so much more was expected from the all-action midfielder. 

Central-attacking-midfield: Kai Havertz (£71m)


There is still plenty of time for Kai Havertz to prove his doubters wrong but there has been scarce evidence to vindicate his £71m transfer fee thus far. 

What is most concerning is that his relatively ineffective displays have been laden with poor decision making and a tendency to occupy pockets of space where it's proven difficult for him to make an impact.

Perhaps his ominous opening to life at Stamford Bridge is a by-product of Lampard's management style, while pertinently he is only 21 and less than six months into his Chelsea career.

There is still plenty of time for the German playmaker to turn things around, but it's been far from an auspicious opening.  

Right-wing: Juan Cuadrado (£23.3m)

Juan Cuadrado signed for Chelsea from Fiorentina in 2015 for a considerable £23.3m fee but made just 15 appearances - including four league starts - during his stay. 

Juventus eventually secured his signature on a permanent basis following back-to-back loan spells with the Old Lady, ending the Colombian's unhappy marriage with the Blues. 

Left-wing: Timo Werner (£47.7m)


Like Havertz, there's time for Timo Werner to omit himself from this XI. 

The Germany international has shown flashes of brilliance since signing from RB Leipzig but myriad missed opportunities in front of goal have placed his finishing ability under the microscope. 

At £47.7m Werner is the second-most expensive player in this XI, and until Chelsea see a significant return on their investment there will be serious question marks over his suitability to the club and vice versa. 

Perhaps all he needs is a confidence-boosting goal to set him on the path to front running potency.  

Centre-forward: Andriy Shevchenko (£30m


There were a handful of options to consider at centre-forward but Andriy Shevchenko gets the nod over Alvaro Morata and Fernando Torres. 

The prolific Ukrainian was regarded as one of the best forwards in world football when he signed for Chelsea following a fruitful seven-year spell with AC Milan. 

A stunning return of 175 goals and 45 assists from 322 games in the famous black and red of Milan warranted his sizable (relative to 2006) £30m transfer fee, but he never clicked into top gear at Stamford Bridge. 

Not only did he fail to hit the heights expected of him on the field, he was embroiled in a public feud involving his manager Jose Mourinho and Abramovich. 

Chelsea's owner, who was naturally determined to see a return on his investment in Shevchenko, attempted to dismiss Mourinho's assistant Steve Clark and replace him with a Russian-speaking Israeli coach in a bid to help the stuttering striker discover his best form. 

In the midst of the power struggle, Mourinho suggested that Abramovich should instruct Shevchenko to "do some work for once" as the relationship between manager and owner rapidly deteriorated. 

The tension eventually culminated, rather inevitably with Mourinho's dismissal in September 2007. 

Following a season-long loan with former club AC Milan in the 2008/09 season, Shevchenko eventually re-signed for another of his former employers, Dynamo Kiev, on a free transfer in 2009 having amassed a return of 22 goals in 77 Chelsea games.

Here's the line-up in full below...

Chelsea all-time flop XI
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