If I had to guess, I'd suggest he's breaking mach1 outside of the atmosphere. When he re-enters he'd slow down to terminal velocity, the parachute will be opening in the same conditions a regular parachute opens, won't it?
Sure, his terminal velocity will reduce - but wouldn't it reduce to the usual earth terminal velocity? The point being he'd slow substantially from his maximum speed to something more manageable and be fairly safe when opening his parachute? No more in danger than any other sky diver at least.So he will probably reach and maintain terminal velocity at some point, but the terminal velocity will change as he falls. And since I'm going to assume he'll be traveling faster than "ground terminal", he will slow down, but he may be going much faster than usual when he gets there.