Unless his helmet is lead, and the rest of his body is the fins (Think: yard dart here.).
I think the “head first” thing isn’t going to happen.
Air’s too thin - he’ll be doing the same uncontrollable tumble the last guy did, until he’s lower and thus out of the thin air needed for the speed. Somewhere in there, there could be a gray zone he can aim for. Don't know.
Ear protection from his own sonic boom? Lets think about that.....
The project was shelved in 1988. Hmmm - I wonder why.
Good luck -
Godspeed -