[Motor31]

Have someone continue to crank the window in as you push it from the outside. Once it pops they should be able to tighten it up against the frame. It that does not work, I'd suggest simply putting a small bead of silicone caulk around the window where it mates up with the frame and let it set, then close the window against the new seal. Or you could get a small strip of foam weather seal that has adhesive on one side and line the frame with it to form a barrier to the wind.

It sounds like your window frame may be bent, preventing the surfaces to mate up.