If you winkle information out of someone, you get it from them when they do not want to give it to you, often by tricking them. The security services will pretty well go to any lengths to winkle out information The detective was trying to winkle information out of her. = worm out
If you winkle someone out of a place where they are hiding or which they do not want to leave, you make them leave it. He somehow managed to winkle Picard out of his room Political pressure finally winkled him out and on to a plane bound for Berlin It will not be easy to winkle out the old guard and train younger replacements
the main character in a story by Washington Irving, who sleeps for 20 years and finds that the world has changed a lot when he wakes up. Rip Van winkle. Rip Van Winkle