Originally Posted by
Tarq57
I would imagine that its because the speed of an aeroplane diving near-vertically (without such things as beta prop pitch) would easily exceed the free fall speed of a skydiver.
I can only assume you have not looked at videos of the other skydiver entries to aircraft in descent. All previous successful attempts have used a drogue chute to control the rate of descent of the target aircraft in a near vertical dive.