I don't mind throwing it deep on 3rd and 1 at all. It would have worked too, Watkins was wide open. If TT had a concussion they woudn't have let him back in, have to assume he's fine and he just f'd the throw up.
The problem is that he's not sitting back in the pocket forever. He's getting rid of the ball quickly with lots of guys in coverage and they still can't stop it.
It would have been spectacular had he caught it, so I don't know about "should." If he catches it it's a TD though because the only reason he fell down was trying to catch it on the 2nd effort.
It's not just Gilmore. Darby looks average and so do the safeties. The entire "elite" secondary looks average, in large part because there is no pass rush.