Chelsea FC’s Top 30 Transfers Of All Time

LONDON, ENGLAND - MAY 03: Didier Drogba of Chelsea celebrates winning the Premier League title after the Barclays Premier League match between Chelsea and Crystal Palace at Stamford Bridge on May 3, 2015 in London, England. (Photo by Clive Mason/Getty Images)
LONDON, ENGLAND - MAY 03: Didier Drogba of Chelsea celebrates winning the Premier League title after the Barclays Premier League match between Chelsea and Crystal Palace at Stamford Bridge on May 3, 2015 in London, England. (Photo by Clive Mason/Getty Images) /
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17 Feb 2002: Jimmy Floyd Hasselbaink of Chelsea celebrates scoring a goal during the AXA sponsored FA Cup fifth round match against Preston North End played at Stamford Bridge, in London. Chelsea won the match 3-1. \ Mandatory Credit: Ben Radford /Allsport
17 Feb 2002: Jimmy Floyd Hasselbaink of Chelsea celebrates scoring a goal during the AXA sponsored FA Cup fifth round match against Preston North End played at Stamford Bridge, in London. Chelsea won the match 3-1. \ Mandatory Credit: Ben Radford /Allsport /

23. Jimmy Floyd Hasselbaink – Fee: £15m

Jerrel (‘Jimmy’) Floyd Hasselbaink was a character, wasn’t he? The Dutch striker joined Chelsea as a highly-rated 28-year-old. His whopping transfer fee in fact matched the English record at the time, only adding to the pressure on his broad shoulders.

After scoring 24 La Liga goals in the previous season, Hasselbaink merely picked up where he had left off, hitting the back of the net 23 times in each of his first two Premier League campaigns. During his four-season stint, the forceful forward scored 88 goals in 177 competitive appearances.

Unfortunately, his tenure corresponded with the dry spell just before Jose Mourinho’s arrival, but he was nonetheless widely feared across world football. He won his second Premier League golden boot during this phase in his career, having previously won it with Leeds United. He was also a key part of the team who reached the heady heights of the Champions League semi-finals, losing to AS Monaco.

Although there was little material reward for his efforts, any Chelsea fan of the appropriate vintage will testify that Hasselbaink is one of the greatest strikers to ever pull on a blue shirt.

While his playing career only headed downhill after leaving Stamford Bridge, his passion has translated over into the world of management. He took Burton Albion to the summit of League Two, before Queens Park Rangers came calling in November 2015. It would not be surprising to see the Dutchman lead Chelsea’s rivals back to the Premier League in the immediate future.

Next: #22