Originally Posted by cherokeesam
But then he has no reason to actually *keep* the wings, beyond the shakedown cruise; and it would be a head-scratcher to try to make an "equipment tester" suddenly become Captain America's new sidekick.
There has to be a legitimate reason for him to get the wings, *and* keep the wings. As well as a legitimate reason for him to become Cap's right-hand man.
You have him become Cap's friend throughout the course of the film, and he ends up assisting him in whatever third act, "world in peril" scenario he finds himself in. He served his country and did it well, so Fury promotes him to a field agent.
His wings are what he knows, so he keeps them. Sort of like Hawkeye's bow.
It's really not all that hard to justify that kind of stuff.