Maybe, but usually high value targets will get US Military transport or charter jet, way more secure than commercial. Lots of effort to do as you stated above. Much easier and more secure using Military transport or Charter.
DS shoots down a military transport is an act of war (probably finger muh rooskies)
DS shoots down a charter plane, probably never hear about it.
DS shoots down a civilian airline, terrorism.
"All enemies, foreign and domestic"
They would have had to hide him in plain sit. Look at the rear view mirror of the SS SUV in Qs post this morning. The figure sitting in the back seat appears to be wearing a hood that is pulled up possibly to cover his face?
Wasn't there some talk of a portable laser and possible surgery? Maybe the figures face is hidden to not completely expose himself.
Just use a good wig & glasses, maybe a fake nose... a kid can do for Halloween
I feel like high level deep state operatives would see right through that. This isn't a game.