Who Is The Most Expensive Chelsea Transfer Fail Of All Time?

Roman Abramovic didn't become an oligarch by making bad financial decisions; his business savvy, along with shrewd political connections and a healthy moral deficit have allowed him to amass a personal fortune of around $8 billion. 

Which makes the profligacy he's overseen at Chelsea all the more staggering. Many fabulous players have graced Stamford Bridge, both BR (Before Roman) and since: Cesc Fabregas, Claude Makelele, Frank Lampard and Didier Drogba to name but four. But the last 10-15 years have also been marked by some truly disasterous financial decision-making; the sort that no self-respecting business tycoon should make.

So in the week that Kevin de Bruyne was sold by Wolfsburg for $83 million, just 18 months after Chelsea sold him for fully $57 million less, we bring you Chelsea's five most financially disasterous transfer decisions. We're not saying the below are necessarily bad players, just that their transfer - in or out of the club (or both) - was a piece of monetary madness.

In descending order of fiscal ineptitude:

1. Kevin de Bruyne

Chelsea sold de Bruyne for $26 million. Now Wolfsburg is selling for $83 million. (Photo: @caughtoffside | Twitter)

Chelsea signed de Bruyne as a 21-year-old from Genk for the modest sum of $10 million in 2012. Afforded just three appearances during his two seasons at the club, the Belgian was offloaded by Jose Mourinho, sold to Wolfsburg for the tidy sum of $26 million.

So far, so good. Except, in the 18 months since he left Chelsea de Bruyne has turned into one of Europe’s most devastating attacking midfielders, leading Europe in assists last season with 20. Which is why Man City are prepared to pay a staggering $83 million for his services. Mourinho had one of Europe’s brightest midfielders on his hands and let him go for comparative chump change. Worse still, he’s now at their biggest rival for Premier League supremacy.

Oh, and Chelsea even failed to put a sell-on clause in the sale to Wolfsburg. 

2. Fernando Torres

For those of you keeping track, that's $4 million per goal. (Photo: @TFS_Chelsea | Twitter)

Signed for a then British transfer fee record of $80 million midway through the 2010-11 season, within seconds of the ink drying on his contract Fernando Torres went from being one of the most electric strikers of the Premier League era to a man with all the confidence of an acne-riddled 14-year-old boy at a school dance. With braces. And a tank top knitted by his mother.

In fairness, Torres was already on the decline during his last half-season at Anfield, bereft of that extra edge since knee surgery in April 2010. It took him 903 minutes – you could watch all six Star Wars episodes in that time – of football to score his first Chelsea goal, and he contributed just 20 league goals in his five seasons at the club. Torres was offloaded to AC Milan midway through last season for..... absolutely nothing.

3. Winston Bogarde

$90,000 per week to do what? (Photo: @ohis_ | Twitter)

One from the pre-Abramovic era now. Dutch international defender Winston Bogarde was signed from Barcelona at the start of the 2000-01 season on a free transfer by then-manager and all-time heartthrob Gianluca Viali, only for the bald Italian to be replaced by Claudio Ranieri shortly thereafter. Ranieri didn’t fancy Bogarde and wanted him gone. Except, our Winston was very happy with his $60,000 per week contract ($90,000 in today's money), and had no intention of going anywhere. In his four years at the club he played just nine times, making zero Premier League appearances in his final three seasons. He was demoted to the reserves, then made to train with the youth team in a bid to force him out the club, but Winston kept diligently turning up, day-in, day-out to collect his pay check, like the model professional he was.

On his time at Chelsea, Bogarde is philosophical: “This world is about money, so when you are offered those millions you take them…I may be one of the worst buys in the history of the Premiership [as it was then] but I don’t care.”

Ah, the beautiful game.

4. Juan Cuadrado

Offloaded to Juventus (Photo: @TeleFootball | Twitter)

Is it too early to consider Cuadrado one of Chelsea’s biggest transfer cock-ups? After all, they only signed the Colombian in January for the princely sum of GBP27 million.

In a word: noitisdefinitelynottooearlynotevenalittlebitearly. Cuadrado managed just 312 minutes of football in a Blues shirt last season, though Mourinho clearly saw enough to convince him he’d made an error of judgement: after just seven months Juan has already been offloaded to Juventus on loan for the rest of the season. While Chelsea's policy of acquiring young players for a modest fee and loaning them out across the globe for half their career is well established, Cuadrado is 27-years-old and cost Chelsea many, many millions. 

It's not entirely clear how much of Cuadrado's $130,000 per week salary Chelsea are still paying.

5. Nemanja Matic

Great player, terrible piece of business. (Photo: @ChelseaFC | Twitter)

Chelsea first signed Nemanja Matic back in 2009 from Serbian side Kosice for a shade over $2 million. When you consider the player Matic has become, and how pivotal he is to Chelsea’s system, that looks like a fabulous piece of business. Except, Chelsea "gave" Matic to Benfica in  2011, along with 32 million bucks, in return for Sideshow Bob impersonator and occasional centre back David Luis. Chelsea then had to pay another $32 million to Benfica in 2014 to welcome Matic back to Stamford Bridge.

Mercifully for Chelsea, there's an even more profligate force in the footballing galaxy: Paris St Germain. PSG's Qatari money-men handed over an eye-watering $65 million for Luis at the start of last season, somewhat easing the financial impact of their Matic mistake.