Winky Gaines was a male Human of 20th century Earth. He was a professional athlete who participated in boxing contests.

In 1930, he fought Charley Delaney in Bay Land Garden in San Francisco. Gaines was the challenger. (DS9: "Past Tense, Part II")

This character was only mentioned in writing.
Winky Gaines replaced Gus Barnes on the boxing poster, which first appeared in "The City on the Edge of Forever".