Chelsea FC’s 50 Greatest Players Of All-Time

A giant Chelsea flag flies before kick off of the English Premier League football match between Chelsea and Everton at Stamford Bridge in London on January 16, 2016. AFP PHOTO / JUSTIN TALLISRESTRICTED TO EDITORIAL USE. No use with unauthorized audio, video, data, fixture lists, club/league logos or 'live' services. Online in-match use limited to 75 images, no video emulation. No use in betting, games or single club/league/player publications. / AFP / JUSTIN TALLIS (Photo credit should read JUSTIN TALLIS/AFP/Getty Images)
A giant Chelsea flag flies before kick off of the English Premier League football match between Chelsea and Everton at Stamford Bridge in London on January 16, 2016. AFP PHOTO / JUSTIN TALLISRESTRICTED TO EDITORIAL USE. No use with unauthorized audio, video, data, fixture lists, club/league logos or 'live' services. Online in-match use limited to 75 images, no video emulation. No use in betting, games or single club/league/player publications. / AFP / JUSTIN TALLIS (Photo credit should read JUSTIN TALLIS/AFP/Getty Images) /
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41. Terry Venables: 1960-66

If Chelsea FC held a contest for “most interesting man” to ever play for the club, Terry Venables would be at the top of the rankings for the honor. Starting his career in the Chelsea academy, the London native graduated to the first team 1960 and spent six years with the club, making 237 appearances.

Venables lifted the League Cup in 1965 but was shipped out to Tottenham Hotspur after a series of conflicts with manager Tommy Dougherty for £80,000. The decision would come back to bite Chelsea as the midfielder helped lead Spurs to a victory over Chelsea in the FA Cup Final in 1967.

It was after his playing career was over that Venables became such an interesting character. He began his managerial life with Crystal Palace after making 14 appearances for the Eagles as a player in 1976 and stayed at Selhurst Park for four seasons.

He then went on to manage Queens Park Rangers for four years, Barcelona for three, Tottenham for six, and Crystal Palace, Middlesbrough, and Leeds United for a year each. In the mid-1990’s he also managed England and Australia for two years and one year respectively.

His honors as a manager are lengthy including helping Crystal Palace go from the third division to the first, winning La Liga with Barcelona, and an FA Cup with Tottenham in 1991. Venables was clearly just as adept at managing a football team as he was captaining one from midfield.

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