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.

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20 Best – Jimmy Floyd Hasselbaink

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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.

He scored 23 league goals in his first season with the Blues and won the Premier League Golden Boot. The next season he again scored 23 league goals but missed out on the Golden Boot by a solitary goal. His blistering volley against Manchester United is considered as one of the greatest Chelsea goals ever. A total of 46 league goals in his first two seasons was the kind of statistic Chelsea fans could only dream of at that time, and hence Hasselbaink correctly earned legendary status at the club.

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.

Falcao played just 10 league games for Chelsea, scoring just 1 goal, as Chelsea endured their worst ever season under Roman Abramovich. Though Chelsea did not pay anything to sign him, his wages were ridiculously high and signing him prevented the club from signing another potentially brilliant striker who could have helped the club in times of crisis, something he completely failed to do.

18 Best - Juan Mata

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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.

Though he missed his penalty in the Champions League Final shootout, it was his corner which was converted by Didier Drogba in the last minute to take the game to extra time. Mata was awarded the Chelsea player of the year trophy in both his full seasons at the club and will surely be adored by the Blues faithful for a long long time, despite eventually moving to archrivals Manchester United.

17 Worst - Tal Ben Haim

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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.

Despite his evident incompetence at the top level, Ben Haim started many games initially, primarily due to long-term injuries to first choice center backs John Terry and Ricardo Carvalho. However, after they returned to action, Ben Haim found himself as the 4th choice center back at the club and barely started another game after that. This was followed by a public outburst against then manager Avram Grant, for which he was fined two weeks wages as well as $120,000.

16 Best - Eden Hazard

Chelsea's mercurial number 10 is one of only two current Chelsea players on this list and though he has only been at the club for 4 years yet, it was impossible to leave him out. Easily one of the best dribblers the game has ever seen, Hazard has the ability to single-handedly change the game with a moment of sheer brilliance. He was the chief architect behind Chelsea's dominance in the 2014/15 season as they marched towards the Premier League title. He was also given the PFA player of the year award for his exploits in that season. Though his form dipped tremendously last season, he is back to his very best under Antonio Conté and has already bagged seven goals in 11 matches this term. Hazard is a once-in-a-generation talent, and is widely expected to compete with the likes of Neymar and Gareth Bale to be the player who will finally end the Ronaldo-Messi duopoly over the Ballon D'or award.

15 Worst – Claudio Pizarro

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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.

The purchase of Nicolas Anelka pushed him further down the pecking order. He finally managed to end his goal drought with another goal against Birmingham City, ending his Chelsea career with a miserable tally of just 2 league goals. He was offloaded back to Germany, where he against enjoyed a few prolific seasons, meaning his stint at Chelsea was the only real blip in his erstwhile brilliant career.

14 Best – Jimmy Greaves

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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.

The English striker made his debut for Chelsea at the age of just 17, and ended his first season as the club’s top scorer, with 22 league goals. He went on to score a staggering 124 league goals in just four seasons with the club, at an unprecedented rate of 31 goals/season. He also holds several records in English football, such as being the highest goal scorer in the history of English top-flight football, as well as being the only player to score 6 hat tricks for England in international football. Had his career not been cut short due to alcoholism, Greaves would have been regarded as one of English football’s greatest legends.

13 Worst - Juan Cuadrado

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The versatile Colombian wingback arrived at Stamford Bridge with a glowing reputation, having had a stellar 2014 FIFA World Cup campaign, where his pace and trickery ensured he was one of the standout players of the tournament. Chelsea beat a host of other top clubs to secure his signature in January 2015. With his blinding pace and ability to play almost anywhere on the pitch, Cuadrado was expected to be a major asset for Mourinho’s Chelsea side, however he soon proved to be a liability instead. The Colombian made just three starts in the Premier League for Chelsea before being shipped off to Juventus on loan. His lack of playing time was largely down to injuries as well as poor form whenever he was given a chance. Cuadrado shone for Juventus on loan, and despite new manager Antonio Conté publicly praising the player, he left again on for Juventus on a threeyear long loan, effectively ending his Chelsea career and proving to be a complete waste of $32 million.

12 Best – Peter Osgood

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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.

Osgood continued his prolific form in big matches next season as well, scoring in both legs of the final of the European Cup Winners’ Cup against the mighty Real Madrid, giving Chelsea a taste of European success for the first time ever. These trophies mean Osgood will forever have a place in the hearts of Chelsea fans all over the world, and there is a huge ‘Born Is The King’ banner at Stamford Bridge as a tribute to the great forward.

11 Worst - Juan Sebastian Veron

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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.

However that proved to be his only goal for the club as he soon tore his hamstring and missed a major of the 2003/04 season, playing just seven times in the Premier League. As soon as Jose Mourinho took charge of the club in 2004, the first decision was to ship out Veron on loan, and the Argentine never played for the club again, making just 15 appearances in total.

10 Best - Petr Cech

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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.

Despite a life-threatening head injury in 2006, Cech continued playing with a now infamous head cap, and cemented his status as one of the very best in the world. He holds several Premier League records, but his biggest achievement was winning the Champions League trophy in 2012, where he saved three penalties and went the the right way for all six penalties he faced during the final.

9 Worst - Khalid Boulahrouz

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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.

He could never really reclaim his starting spot as John Terry and Ricardo Carvalho had both cemented their places at the heart of the Blues’ defense. Boulahrouz was often played as a right back, and struggled to adapt to the pace of the Premier League, with average opposition wingers often getting the better off him in one on one duels. His form dipped drastically and he played just 13 league games in two years at the club, with the final straw being Mourinho’s decision to field Michael Essien as a center back despite Boulahrouz being fit.

8 Best – Gianfranco Zola

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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.

In the 1997/98 season, Chelsea won three major trophies with Zola as their talisman, with the Italian scoring the winning goal in the final of the European Cup Winners’ Cup. Zola also won another FA Cup with the club in 2000, assisting Roberto Di Matteo’s goal in the final. The Italian will always be fondly remembered for his positivity and smiling nature, as well as his incredible back-heel goal against Norwich city during his penultimate season in London.

7 Worst - Shaun Wright Phillips

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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.

Though he did pick up his form in the 2006/07 season, he could not make the most of his extended run in the starting lineup and soon was benched again. In three years at Chelsea, Wright Phillips made 65 substitute appearances, compared to just 60 starts, which proves that he could never really settle at the club and turned out to be an expensive flop.

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.

Lampard is the highest goal scorer in the history of Chelsea Football Club, with a staggering 211 strikes in 648 games. He has won three Premier League titles with the club and was arguably the club’s standout player in all three of those campaign, including a stunning 27 goal season in 2010, remarkable figures for a central midfielder. Lampard was also the captain of the side that defeated Bayern Munich at the Allianz arena in 2012, with Chelsea winning their maiden Champions League title. A firm fan favorite at the Bridge, Lampard has surely earned the right to be worshipped by the Blues’ faithful.

5 Worst - Adrian Mutu

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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.

Then, in September 2004, Mutu failed a drug test when he tested positive for cocaine, and was subsequently released by the club with immediate effect. As of 2013, Mutu has been ordered to pay Chelsea more than $20 million in compensation, with a lengthy case still going on.

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.

It was fitting that the club’s greatest ever forward won the Champions League with his last ever kick, in the penalty shootout against Bayern in 2012. However Drogba returned in 2014 and guided a young Chelsea side to another Premier League title to establish himself as one of the Premier League’s all time greats.

3 Worst - Andriy Shevchenko

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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.

It all started beautifully for the striker with a brilliantly taken goal against Liverpool in the Community Shield on his debut. However, several injuries combined with the exceptional form of Didier Drogba meant that Shevchenko faced an extended spell on the sidelines, and could never really grab the opportunities he occasionally got. After just 14 goals in two full seasons, Shevchenko was shipped off back to Milan on loan, with his transfer being deemed as an expensive flop, as he could simply never adapt to life in the Premier League.

2 Best - John Terry

John Terry is undoubtedly Chelsea's biggest living legend. Loyal to the club since he was a 7-year-old ball boy at Stamford Bridge, Terry has skippered his boyhood club during the most successful period in their history. Still going strong at the age of 35, Terry's reading of the game as well as his aerial ability is unmatched, with a record 40 Premier League goals a testament to that attribute. Many top forwards in the game have regularly rated Terry as their toughest ever opponent, and he is widely rated as the most inspirational captain in the Premier League, if not the world. Terry has captained his way to four Premier League Titles, five FA Cups, three domestic cups, one Europa League and most importantly, the holy grail, i.e the club's maiden Champions League title in 2012. He also scored some of the most memorable goals in the club's history and has cemented his status as Chelsea's greatest ever player.

1 Worst - Winston Bogarde

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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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