The Winkster is a character who only appeared in Barney Live! In New York City. While he is the closest thing to a real antagonist the Barney series has ever gotten, (next to Cody from Barney's Great Adventure) he is not really bad, just a silly fellow who likes playing jokes and tricks, and disappears as "quick as a wink". He takes the Barney Bag while Barney and the other kids are helping get Baby Bop's blanky unstuck out of the door crack to the playhouse. Throughout the show, the kids chase him around the clubhouse and have to catch him so they can show the special surprise inside the Barney Bag. He later explains that he took the bag because he wanted to have friends to play with him and thought getting everyone to chase him would help him make the friends he never had.

He is portrayed by both David Voss and Ashley Wood.