Okay, I’m home and have time to answer some of the skydiving-related questions people have asked. For the record, I’m an experienced skydiver, I’ve made over 1000 jumps including 3 from a 727. I was a certified Jumpmaster for years and took a lot of people up for their first jump. I can go into greater detail about my “credentials” if anyone is interested.
I’ll start with the exit. I don’t believe Cooper had any idea where he was. He didn’t expect to jump at night. One of his demands was that the plane refuel and take off by 5 pm. It didn’t take off until after 7:30 pm. The plane was flying at 10,000 ft. when he jumped. The cloud ceiling was at 5,000 ft so he couldn’t see the ground. He jumped blind, into the night. I think this also rules out getting help from an accomplice or having a car hidden and waiting. Only pure luck could have put him anywhere near a pre-planned landing area.
The plane was going almost 200 mph. The wind blast would have sent Cooper tumbling head over heels. That’s what happened to me on my first 727 jump and the plane was only going about 150 mph. The temperature at 10,000 ft. was about 19F. Cooper did not have gloves or head cover. The shock of the cold air would have made him tense up. It’s very difficult to get stable for a safe opening when you’re tense and stiff. Also, sensory overload could have caused his mind to go blank, as Gray Ghost suggested.
The wind could easily have blown his ripcord handle out of its pocket, making it very difficult to find, especially with cold numb fingers. If his handle was dislodged, he could easily have hit the ground while trying to find it. Plenty of skydivers have died this way.
The wind could also have blown his container open, possibly shredding the canopy as someone suggested, more likely wrapping him up in the lines if he was still unstable. This would be a Bad Thing. The wind could also have blown his bundle of money away. If he did manage to find himself alive under an open canopy at 9-10,000 ft. a 30 knot wind could have blown him several miles. I know this from experience; I’ve opened high on a windy day and drifted at least 5 miles before landing.
If he managed to get stable, freefall through the clouds and open his canopy before impact, he still would have had to land in the dark on unfamiliar and probably uneven ground- an excellent way to sprain an ankle or worse. Or he might have crashed into a tree, another good way to break a bone or two.
On my night jumps, we always had the landing area well-lit and we could see it from the plane before exiting. Jumping into the dark unable to see the ground is a recipe for disaster. Again, I don’t think Cooper was expecting to face that situation.
So, I think it is possible but extremely unlikely that Cooper survived. I also think, as I said before, that he probably had some parachuting experience- just enough to make him think he could pull it off.