The Western quadrant of Oz was once ruled by a beautiful Princess and enchantress named Gayelette, who lived in a small Kingdom and ruled over the Winkies wisely and well. She also owned a beautiful magic Golden Cap encrusted with many sparkling diamonds and rubies. The Golden Cap was also tied to the Winged Monkeys of Oz. After the mischievous creatures played a mean prank by throwing the richly dressed husband of Gayelette in a river on her wedding day, Gayelette was enraged. So, as punishment she made the Winged Monkeys slaves to the Golden Cap and had to listen to whoever wore it three times. After her reign ended the cap fell into the hands of The Wicked Witch of the West. With the help of the Winged Monkeys, the Winkie people were enslaved for many years to endlessly work hard for their new ruler and she treated them very cruelly.
Sometime later, the Wizard eventually came to Oz and tried to overthrow the Wicked Witch of the West. But she used the charm of the Golden Cap to have the Winged Monkeys run him out of her territory. After that a little girl named Dorothy Gale and her little pet dog Toto from Kansas were sent by the Wizard himself to kill her in exchange to be sent back home again. The girl and her dog were also accompanied by a Scarecrow, a Tin Woodman and Cowardly Lion. The Witch used the Cap one last time to order the Winged Monkeys to seize the girl, her dog and the lion. When Dorothy was imprisoned by the Wicked old Witch she melted her away with a bucket of water after she tried to steal one of the girls' Silver Shoes which had many mysterious powers. When Dorothy defeated the Witch, there was great rejoicing, and the day was set aside as an annual holiday. The Winkie people asked the Tin Woodman to be their new official Emperor, and he gladly accepted and has ruled over them successfully ever since, even living in a Tin Castle that was built by the Winkies in his honor. (The Wonderful Wizard of Oz)
Winkies of 1939
In the 1978 African-American version The Wiz, the Winkies are slaves to an underground sweat shop in Oz.