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The Sidewinder Syndicate were an organised gang of reptile gangsters encountered by the Doctor in his second, tenth and eleventh incarnations.
History
The Sidewinder Syndicate's ancestors were stranded on Old Earth in Chicago during the 1920s and adopted the methods and mannerisms of the Chicago gangsters enthusiastically. (AUDIO: House of Cards)
The Tenth Doctor met the Sidewinder Syndicate during a visit to a bar in America. The Syndicate attacked the bar, then left. The Doctor, Heather McCrimmon and Wolfgang Ryter tracked them down to a shop in the city were they were met by Snake-Eyes. The Doctor sent them home in their ship by scaring them with an animal picture book which included sharks and lions. (COMIC: Snakes Alive!)
The Eleventh Doctor and Amy Pond met the Syndicate in a alien bank run by Ratlings. The Sidewinder Syndicate wanted their money from the bank, so they stormed it, demanding its return. When they received it, they realised it was fake. Amy discovered that the Ratlings had tried to hide the money from them. She showed them the real money in the vault. The Doctor and Amy left, allowing the Sidewinder Syndicate to deal with the Ratlings. (COMIC: Money Troubles)