It look's like floor is pushing jambs upward and over crown moulding. Removing 1/2" from bottom of jambs might alow door returning to original position.

I suppose that show's how deceiving pictures can sometimes be. The first and last pictures are totally different depictions.

The left door trim(vertical) is beginning to pull away from the wall---looks like normal settling. The top trim(under the crown molding) seems to be pulling away more. While that might be caused by the settling/floor, it seems to me that the top trim and crown molding were not sufficiently secured to the framing.

All we can do is our best guesses, no way to actually determine the cause from here.

Yes, I thought it was not secured properly. So do I just caulk the space or try to drive a very long wood screw in to a stud and then patch the hole and repaint trim? What a pain!

What Kudzu said, it wasn't nailed to the wall or not fastened good, and from the door opening and closing it moved away from the wall.