Earlier quoted context omitted.
Yes but it won't make a sonic boom.
If the wind is unstable, and slows down, can't the plane break it just out of inertia?
Fluid dynamics basically means that it is impossible for any parcel of air to have an instant demarcation from nil wind to 300 knot wind without going through a (very very turbulent) transition layer. And 300 knot winds?? Maybe routine on Venus or Jupiter, but very very rare if not nonexistent on Earth.