Chelsea's 5 Best And 5 Worst Signings Of All Time

With news emerging that Chelsea is prepared to make Shakhtar Donetsk forward Alex Teixeira the first signing of the Guus Hiddink era (Part II) for a reported £30 Million, the Blues are once again relying on owner Roman Abramovich’s checkbook to build a winning squad once the transfer window opens in January. Like any other major club, Chelsea has had its successes and failures in the transfer market. As January 2016 begins, let’s take a look at Chelsea's best signings and worst signings of all time. We'll start with the bad news for Chelsea fans first.

Related: Chelsea Rejected These 11 Players, But Together They Would Tear Up Any Team In Europe

Chelsea's Worst Signings Of All Time

#5 – Shaun Wright-Phillips

Cost: £24 Million from Manchester City, 2005

Chelsea's Worst Signings – Shaun Wright-Phillips

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One of the most frustrating players in Chelsea’s history. He would dazzle with incredible runs, jukes, and moves with the ball before launching his shot 30 yards into the stands. He was like a soccer version of Allen Iverson, but without any ability to finish and only “slightly” less gangsta. It got so bad that on the version of EA Sports FIFA when he was still with the Blues, I celebrated selling him to a club in South Korea. I couldn’t have been prouder of myself. Which I think sums up the Shaun Wright-Phillips era at Chelsea. He’s currently playing with his brother on the New York Red Bulls, which seems to be a much better fit for him.

#4 – Juan Cuadrado

Cost: £23.3 Million from Fiorentina, 2015

Chelsea's Worst Signings – Juan Cuadrado

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This also went poorly. After arriving with much fanfare in January 2015, Cuadrado flamed out in spectacular fashion and failed to adjust to life with Chelsea in the Premier League. He consistently had problems dribbling, passing, and shooting, but other than that, he was a great player. Mercifully, he was shipped out on loan to Juventus in August, after which he actually thanked God for getting him away from West London. Coincidentally, these prayers coincided with Chelsea supporters' pleas to the Almighty to make it stop. Based on how this season played out, it appears Chelsea’s prayers were answered, but only with a hilarious twist befitting Elizabeth Hurley’s devil in the classic movie Bedazzled.

At Juventus, he has played very well when not injured, showing pace on the wing that made Chelsea buy him in the first place. For more recent fans, his failure is the benchmark from which future transfer failures will be measured. So in that regard, well done Juan.

#3 – Khalid Boulahrouz

Cost: £9 Million from Hamburg, 2007

Chelsea's Worst Signings – Khalid Boulahrouz

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Nicknamed “Khalid the Cannibal” for his ability to “eat up” opponents on the pitch, Boulahrouz was supposed to provide cover in midfield and at centre back, but never really found a role at the club. After bizarrely taking the #9 jersey as a defender, he only made 20 appearances for the club in all competitions and generally did nothing of interest to justify his hype. He spent the 2007-08 season on loan at Sevilla and never played another game for the Blues. I’d like to come up with a joke or sarcastic comment here, but I honestly cannot remember a single thing that he did for the club while he was there, good or bad. Probably not a “great” sign.

#2 – Adrian Mutu

Cost: £15.8 Million from Parma, 2003

Chelsea's Worst Signings – Adrian Mutu

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Unlike the other players on this list, Mutu did not excel at playing crap football for Chelsea. In fact, when he played, he often looked very good, scoring four goals in his first three matches. However, he tested positive for cocaine in September 2004 and was released by the club a month later. But that was only the start of the discord between Mutu and Chelsea, as Chelsea filed paperwork with the FA to seek compensation from Mutu for his breach of contract. After countless rounds of appeals, ultimately the FIFA Dispute Resolution Chamber ordered Mutu to pay €17,173,990 in compensation to Chelsea for the transfer fees paid to Parma, agents fees, and sign-on fees, which was the highest fine FIFA had leveled to that point. Shockingly, Mutu has yet to pay the fine. 

#1 – Andriy Shevchenko

Cost: £30 Million from AC Milan, 2006

Chelsea's Worst Signings – Andriy Shevchenko

Photo: @Chelsea_FC_Girl | Twitter

Oh Sheva. A dominating force at AC Milan, Shevchenko was never able to replicate that form for the Blues. What was initially thought to be a dynamic partnership with Didier Drogba led to Shevchenko on the bench and Mourinho’s relationship with Abramovich deteriorated to the point where the Special One left in September 2007. Emblematic of all that was wrong with Chelsea’s transfer policy, as the owner was buying players his manager did not want. He seems like a lovely gentleman, but he is undoubtedly the worst transfer in history for Chelsea.

You’re probably asking yourself, “Why isn't Fernando Torres on this list of Chelsea's worst signings of all time?” Surely this is a mistake.

There is no mistake. Though he had the highest price tag of any Chelsea player and while he certainly did not terrorize defenses the way he did at Liverpool, he always hustled, made runs into the box, defended, and generally worked himself to death every time he donned the Chelsea blue. We know he had his share of flubs, but he also shined when it mattered most and scored one of the most famous goals in the history of Chelsea Football Club. One that secured victory over Barcelona in the 2012 Champions League Semifinal and sent announcer Gary Neville into such a state of pleasure that he had to change his pants.

Related: Atletico Madrid Can Save Fernando Torres

Sorry, if you do that, you’re not on my list. Now if you’ll excuse me, I shall be changing my own pants.

Chelsea's Best Signings Of All Time

#5 – Ashley Cole

Cost: £5 Million (plus William Gallas) from Arsenal, 2006

Chelsea's Best Signings – Ashley Cole

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A controversial signing from rival Arsenal that engendered such hatred from Gooners that he forever became branded “Cashley” and was booed every time he touched the ball. The reason for such hatred was obvious: he was that damn good. Cole served as a critical component on Chelsea’s back line as the club won 1 league title, 4 FA Cups (giving him a record 7 total), 1 Capital One Cup, 1 Europa League, and of course, the Champions League while Cole served as the left back.

He almost did not make this list because for some inexplicable reason, he serially cheated on his wife Cheryl Tweedy, a British pop treasure. I mean...come on mate.

#4 – Claude Makelele

Cost: £16 Million from Real Madrid, 2003

Chelsea's Best Signings – Claude Makelele

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Signed in the summer of 2003, Makelele served as the heartbeat of the Chelsea midfield for the entirety of his tenure, which included the club’s first two Premier League titles under Mourinho. Undervalued at the time, French legend Zinedine Zidane remarked about Makelele’s departure from Madrid to make way for David Beckham, “Why put another layer of gold paint on the Bentley when you are losing the entire engine?”

He was an incredible defensive midfielder and the club has been attempting (mostly unsuccessfully) to replace him ever since he left in 2008. Other than Nemanja Matic’s performance last season, Chelsea has had a hole in the “Makelele role” since the Frenchman left for Paris Saint-Germain. 

#3 – Petr Cech

Cost: £7 Million from Rennes, 2004

The keeper signed for Chelsea for a paltry £7M and has only been the greatest goalkeeper of the Premier League era. With him between the posts, Chelsea won four Premier League titles (admittedly, last year he did not play as much), four FA Cups, three League Cups, the Europa League, and the Champions League final, when Cech saved a penalty from Bayern Munich’s Arjen Robben in stoppage time and another from Bastian Schweinsteiger in the penalty shootout. Chelsea’s backup keepers during this time included such luminaries as Carlo Cuddicini and Hilario. Needless to say, he was fairly important.

Chelsea did Cech a tremendous favor, shipping him across London to Arsenal (over Jose Mourinho’s wishes) this summer so that the club legend’s family would not have to move. A nice gesture befitting what he did for the club, but it is still painful to see him in that Arsenal jersey.

#2 – Didier Drogba

Cost: £24 Million from Marseilles, 2004

The striker still adorns Stamford Bridge to this day with the “Drogba Legend” banner that hangs in the stands. Scoring 104 goals over his two spells with Chelsea, he was an unstoppable force holding up the ball, capable of scoring devastating goals with both feet and his head. An incredibly strong player, defenders seemed to just bounce off of him. And, of course...he scored the tying goal in extra time and then the winning penalty in the 2012 Champions League Final in what was at the time his final touch as a Chelsea player. Let’s take a look.

This is getting rather emotional. We might need to wrap this up.

#1 – Frank Lampard

Cost: £11 Million from West Ham United, 2001

This isn’t going to help. Super Frank. The honors speak for themselves: Chelsea’s all-time leading scorer (211 goals in all competitions), 429 appearances for the club, one of only seven players with 150 goals in the Premier League era (as a midfielder no less), second all-time in the Premier League in assists, and an unstoppable penalty taker. Under-appreciated in his time (in my opinion), Lampard is one of the best players of his generation. He was a box-to-box midfielder that constantly found himself in the right position to drill home goals from all over the box (and far beyond).

Beyond the statistics, players like Lampard, Drogba, and Makelele provided invaluable strength and leadership in the locker room and on the pitch, in strong contrast to the petulant pissants that currently occupy it. Chelsea would not be in the midst of a relegation battle (and probably would still have their manager) if these fine gentlemen still patrolled the pitch in blue. We miss them dearly.

2016 will be an interesting year for the Blues. The squad desperately needs revamping, so many players will be coming in and many will be going out. Undoubtedly there will be some successes and some misses, but Chelsea should take note of the qualities that made the successes club legends when deciding how to splash Roman’s cash.

Chelsea’s next match is Sunday, January 3rd at Crystal Palace at 8:30 a.m. EST. The trainwreck continues.

Follow Mike Smith on Twitter @thefootiegent

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