Chelsea’s Greatest Countdown: No. 20-16

The Top 50 Countdown

We’re getting to the business end of Chelsea’s Greatest Countdown and this week we head into the top 20 players in the club’s history. None of the following 5 currently still play the game but they’ve had a lasting effect on the Blues, with a couple sparking the foreign and successful revolution we’ve seen come to fruition baring fruit over the last decade and a half.

20. Charlie Cooke

Born in Fife, Scotland but Cooke’s footballing home will always be Stamford Bridge. He joined the club in the 1960s from Dundee and went on to play almost 400 games in Chelsea blue. His contributions across the two spells he spent at the club did not go unrecognised at the time, winning two Player of the Year awards during the times of Peter Osgood and Peter Bonetti (both of whom feature higher up on this list). Although he didn’t play in the most successful Chelsea team in the club’s history, playing in both the first and second divisions, he managed to bag an FA Cup winners’ medal and was influential in the side that won the cup in 1970 against Leeds. Cooke provided a cross for Osgood to head home for a late equaliser in the replay at Old Trafford with the Blues going on to score the winner in extra time.

19. Marcel Desailly

The central defender joined Chelsea as a World Cup winner in 1998 and added an immediate sense of credibility to the club. His presence on and off the pitch was enough to get him the captaincy straight after stepping through the door at Stamford Bridge. Desailly went on to play over 150 times in the Premier League but never won the competition. He did however, win an FA Cup in 2000. Frank Lebouf was his defensive partner around the turn of the century and the French pair went on to become one of the most formidable partnerships in England. As captain, Desailly oversaw the transformation of the club from European qualification hopefuls, to Champions League regulars and was also the first player to captain the club after the arrival of Roman Abramovich. His international reputation set up the success that followed after his departure in 2004.

18. Jimmy Floyd Hasselbaink

The Dutch marksman was one of Chelsea’s cult heroes at the turn of the century, being the club’s main goal-scorer for the majority of his time at the club. After successful spells at Leeds and Atletico Madrid, Hasselbaink was signed by Chelsea for £15m, which was an English transfer record at the time and signaled Chelsea’s intent in becoming a major force domestically. Despite being unhappy at the appointment of Claudio Ranieri after his arrival in West London, Hasselbaink went onto score 26 goals in his debut season at the club. His average tally for a season did not drop under 20 during his career at Stamford Bridge and one moment that sums up his spell at the club came in 2004 when he bagged a 30-minute hat-trick in an FA Cup game against Wolves after coming on as a substitute. He may not have always been in favour with Ranieri but he was always adored by the Chelsea faithful.

17. Ruud Gullit

Known as a midfield maestro during his successful career elsewhere in Europe, Gullit started off playing in the back line under Glenn Hoddle. After his move to the Chelsea midfield, success followed his graceful and awe-inspiring nature. Despite playing for only a couple of seasons, Gullit is considered a Chelsea legend and has described his time at the Blues as the happiest of his career. Maybe the freedom he was allowed because he was such a talented player made him think that way. He went on to become manager of the team after Hoddle’s departure and delivered the first major trophy in 26 years as Chelsea beat Middlesbrough in the FA Cup Final. In his second season in charge, he guided the club to 2nd in the league but was dismissed for an alleged disagreement with the board. A sorry end to a potential fairytale.

16. Roy Bentley

His doctor indivertibly caused one of the best goal scoring Chelsea careers in the club’s history. Because of ongoing lung problems, Bentley was advised by his doctor to move down south and so he joined the Blues just after the end of the World War Two. Whilst he was known as a prolific striker, Bentley adopted a false-nine position for much of his time in the Chelsea team, scoring an incredible 150 goals in 367 games. His career in West London spanned 8 years but in that time he sparked an FA Cup revolution. The club went on many a cup adventure after a barren spell in the world’s oldest competition and one of his most famous moments came at Old Trafford in 1950. The Blues downed Manchester United 2-0 thanks in part to a wondergoal from Bentley who fired in from long range. Bentley captained Chelsea to their first ever first division title in 1955 under Ted Drake and will always be remembered fondly for his involvement in a hugely successful period at the club.