The guy in the ‘Captains Chair’ is Brig. Gen. Marshall B. “Brad” Webb is the Assistant Commanding General, Joint Special Operations Command, Fort Bragg, N.C.
Noting that he’s busy with the laptop, I suspect he’s doing the tech stuff to get the images on the screen.
I think the reason the bamster is off in the corner & wearing the baseball jacket is because he’s come inside from being out for a smoke.
No, he just walked in from playing golf. Here'a a picture of him returning to the White House on May 1. Same outfit.