The 10 Best And 10 Worst Chelsea Players Of All Time

Chelsea Football Club is one of the top football clubs in the world today, and has grown in stature ever since they were purchased by Russian billionaire Roman Abramovich in 2003. The owner invested millions in the club’s transfer policy and signed some world-class players who contributed towards the Chelsea’s most successful period in their long history.

However, things weren’t always so bright for the club. Chelsea have faced several relegation battles as well as struggled financially through many decades, and the club was kept afloat by some stunning players down the years. Though Chelsea are historically not as successful as the likes of Manchester United and Liverpool, they are still a culturally rich club with their own set of legends since their foundation.

While Abramovich’s money surely helped the club create a formidable squad, especially the impeccable spine of Cech-Terry-Lampard-Drogba, which led the club to several major trophies, there were also many transfer duds along the way, including expensive flops and inexplicable loan deals. So lets take a look at the 10 best and 10 worst Chelsea players of all time.

20 Best – Jimmy Floyd Hasselbaink


A few years before the Russian millions flew into Stamford Bridge, Chelsea were still considered a force to be reckoned with. While not exactly title contenders, they were infamous for troubling all the top sides in the league and competing for the European places consistently. A huge part of the credit for that goes to prolific Dutch striker Jimmy Floyd Hasselbaink. Signed for a then club record $23 million fee from Atletico Madrid, Hasselbaink established himself as one of the most consistent and prolific strikers the Premier League had ever seen.

19 Worst - Radamel Falcao

Just three years ago, Radamel Falcao, or ‘El Tigre’ as he was fondly called, was the most feared out and out striker in the world of soccer. A record-breaking move to Monaco ensured the player grabbed plenty of headlines in France. However a career threatening knee injury completely turned his career around. Manchester United swooped in to offer the Colombian forward a taste of the Premier League. However, Falcao bombed badly at the club and the fans were relieved that United did not make his move permanent. Then came Mourinho and his tendency to make the most bizarre transfer decisions, and Chelsea signed the former United flop on a year long loan deal. Though Falcao had unmatched aerial ability, predatory movement around the box, a brilliant weak foot as well as a tremendous work rate, his abilities had diminished considerably in England.

18 Best - Juan Mata


The Spanish playmaker is widely considered as one of the most lovable footballers to have ever graced the Premier League. A brilliant role model on and off the pitch for kids all over the world, Mata played some of the best football of his career for Chelsea. Purchased in the summer of 2011, his transfer soon proved to be a bargain as he lit up Stamford Bridge with his unmatched creativity and vision. In addition, his set pieces were a major weapon for Chelsea throughout his 2.5 years at the club. In his debut season, Mata went on to win a fantastic double of the Champions League as well as the FA Cup, playing a pivotal role in both tournaments.

17 Worst - Tal Ben Haim


Another questionable transfer sanctioned by Jose Mourinho, the Israeli center back was never meant to play for a club of Chelsea’s stature, and definitely not ahead of the likes of John Terry, Ricardo Carvalho and Alex. The transfer raised many eyebrows and everyone wondered if Mourinho knew something about the defender that many others didn’t. Those doubts were soon cleared as from his first game itself, Ben Haim proved that he his not up to the sky-high standards of Chelsea Football Club.

16 Best - Eden Hazard

15 Worst – Claudio Pizarro


Peruvian maverick Claudio Pizarro was considered as one of the finest strikers in the German Bundesliga till 2007, playing for two of the biggest German clubs in Bayern Munich and Werder Bremen, and enjoying prolific spells at both. Snapping him up on a free transfer was considered as a masterstroke by José Mourinho. His Chelsea career did not exactly get off to the best possible start, as he missed a decisive penalty in the Community Shield shootout against Manchester United. However, he made amends for that miss soon as he scored a brilliant goal on his Premier League debut in a thrilling 3-2 win over Birmingham City. However, as soon as Mourinho was sacked from his job, Pizarro Chelsea’s career seemed doomed. He fell out of favor with new manager Avram Grant and lost his place in the starting 11.

14 Best – Jimmy Greaves


One of England’s all time greatest goal scorers, Jimmy Greaves had a phenomenal scoring record, and it's a pity that he is not held in the same regard as the likes of Sir Bobby Charlton, despite having superior statistics. Greaves rose through the ranks at Chelsea’s youth academy and may well be the greatest player the club’s academy has ever produced in its history, after John Terry of course.

13 Worst - Juan Cuadrado


12 Best – Peter Osgood


Forty years before Chelsea signed Didier Drogba, Stamford Bridge had another king, that too a local youngster rising through the youth academy. Peter Osgood, or ‘The Wizard Of Os’ as he was fondly remembered as, was a magical forward who was a major reason behind Chelsea’s rise to prominence in the early 1970s. Before Roman Abramovich pumped millions into the club, the 70s were the most successful years for Chelsea, with their talismanic forward in blistering form. He became one of the few players who scored in every round of the FA Cup, as Chelsea marched to the final in 1970. In the final replay at Old Trafford, he scored a brilliant diving header to level the score as Chelsea went on to win 2-1 to win the first ever FA Cup in their history.

11 Worst - Juan Sebastian Veron


One of the most questionable transfer deals in Premier League history was Chelsea splashing out more than $25 million on Argentinian midfielder Juan Sebastian Veron, just two years after Manchester United had effectively ‘wasted’ more than $40 million on him. Veron was a massive flop at Manchester United, and just as he had started to adapt to the pace of the Premier League he suffered several recurring injuries which hampered his career significantly, just why did Ranieri decide to sign him is still a mystery. Just like Shevchenko, Veron started his Chelsea career brightly with a debut goal in a 2-1 win over Liverpool at Anfield.

10 Best - Petr Cech


The 6'5 Czech stopper is a Chelsea legend in every sense of the word. Such was his influence on the club's supporters all over the world that not a single fan criticized him when he moved to arch rivals Arsenal in 2015. Probably the best goalkeeper in Premier League history, Cech was the base of Chelsea's famous spine of Cech-Terry-Lampard-Drogba, the 4 stalwarts who carried the club forward and won several major trophies despite regular managerial turmoil. Cech was a very influential leader in the dressing room and actually learned seven different European languages to help new players settle in at the club.

9 Worst - Khalid Boulahrouz


The Holland international center back joined Chelsea with a big reputation back in his homeland. José Mourinho personally sanctioned his transfer in 2006, paying Bundesliga side Hamburger SV approximately $14 million for his services. Boulahrouz was given the number 9 shirt, a very unconventional number as the number 9 is usually reserved for the primary striker of the game, with Hernan Crespo the previous wearer of that particular number at the club. Despite a promising start to his Chelsea career with some assured displays against the likes of Liverpool and Barcelona in the Champions League, Boulahrouz suffered a major setback with a recurring knee injury, which kept him out of contention for more than four months.

8 Best – Gianfranco Zola


The Italian magician, in every sense of the word, was undoubtedly Chelsea’s greatest ever footballer before the club was purchased by Roman Abramovich. The diminutive forward dazzled the Stamford Bridge faithful week in and week out with his mesmerizing skills on the ball. Regarded as one of the most entertaining foreign players to ever play in the Premier League, Zola was remarkably easy on the eye. In his debut season at the club, Zola become the first player to win the prestigious FWA Player Of The Year award, as he led the club to only its 2nd ever FA Cup title, scoring 4 goals in the process.

7 Worst - Shaun Wright Phillips


Big things were expected from Shaun Wright Phillips as a youngster, and he often delivered at several youth levels. Following in his father’s footsteps was always going to be a huge task, but legendary striker Ian Wright’s son had built quite a reputation as young, pacy winger at Manchester City. After an impressive campaign in 2004, Chelsea snapped him up for a massive $33 million transfer fee. His first season for Chelsea saw him starting just 15 games, with another 22 appearances from the bench. His severe lack of playing time saw him get dropped from England’s squad for the 2006 FIFA World Cup.

6 Best - Frank Lampard

Legendary midfielder Frank Lampard is widely considered as one of the greatest players to ever play in the Premier League. Ever since his controversial transfer from West Ham to Chelsea in 2001, Lampard went on to scale previously unimaginable heights as Chelsea’s number 8. A true box-to-box midfielder, such was Lampard’s influence at the heart of Chelsea’s midfield that he is regarded as the standard by which other central midfielders are currently measured.

5 Worst - Adrian Mutu


Adrian Mutu was one of the hottest young strikers in Europe when Chelsea swooped for him for a fee of over $25 million in 2003. The Romanian had the world at his feet and had impressed several top clubs after a prolific spell with Parma in the Italian Serie A. Chelsea fans could be forgiven for expecting big things from the razor-sharp striker, and he initially did not disappoint either, with 4 goals in his first 3 games for the club. His remarkable run was soon stopped by a slight muscle tear and his performances soon dipped comparatively. Though he still managed a respectable total of 10 goals in all competitions in his debut season, his inclusion on this list is primarily because of a major off-field incident. First, he had a public spat with manager Jose Mourinho, who accused the player of faking an injury.

4 Best – Didier Drogba

In the summer of 2004, Chelsea paid a whopping $33 million to sign a relatively unheard of striker called Didier Drogba, on the back of just one good season in France. Many questioned Mourinho’s sanity following this huge deal, to which the Portuguese manager simply replied: “Judge him when he leaves this club”, and he couldn’t have been more right. Didier Drogba is effectively worshipped by Chelsea fans all over the world. In his nine full seasons at the club, the Ivorian legend scored 157 goals in 241 appearances, including a staggering 9 goals in 8 difference cup finals. Drogba was probably the best big game forward the Premier League had ever seen, and despite his massive frame, he was agile enough to terrorize opposition defenders. His incredible aerial ability combined with his unmatched brute strength as well as his brilliant understanding of the game made Drogba the complete forward.

3 Worst - Andriy Shevchenko


Widely regarded as one of the very best European strikers out there in his prime, Andriy Shevchenko’s record-breaking transfer to Chelsea was doomed from the start. Carlo Ancelotti later revealed that they had conducted several tests at the infamous MilanLab facility to discover that Shevchenko will never get back to his predatory best and hence decided to accept Chelsea’s $45 million offer, a British record at that time, in the summer of 2006. Despite being one of the most feared strikers in the game, many were doubtful as to how the Ukrainian legend will manage to brush off his enormous price tag.

2 Best - John Terry

1 Worst - Winston Bogarde


One of the most iconic Premier League transfers of all time, in a negative way, was the signing of Holland international Winston Bogarde in 2000. He was actually a decent defender with impressive credentials when he was signed – already played for two of the biggest clubs in the world i.e Barcelona and AC Milan as well as earned 20 caps for his country. However, after a spate of injuries, he simply could not perform up to the mark in the Premier League. It was reported that within two months of taking charge at the club, Claudio Ranieri wanted the defender out of club citing that he is not up to Chelsea’s standards.

Bogarde rarely every played for Chelsea, making just nine appearances in four years. However, he gained worldwide attention for his notorious attitude towards the game when he suggested that he will happily see out his Chelsea contract instead of looking for first team opportunities at other clubs. Chelsea tried their best to offload him and get rid of his ridiculous $65,000/week salary but to no avail, as the player happily stuck on till his contract ended, and justified his decision by saying: “ Why should I throw 15 million Euros away when it is already mine?

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The 10 Best And 10 Worst Chelsea Players Of All Time