1.
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. ( BRIT INFORMAL )
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
PHRASAL VERB : V P n (not pron) , V n P of n , also V n P
2.
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. ( BRIT INFORMAL )
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.
PHRASAL VERB : V n P of n , V n P , V P n (not pron)