I wish I could say I thought of that question myself, but that would be as much of a lie as Jasper Sitwell’s allegiance to S.H.I.E.L.D.
No, it’s just one of the questions that the crew at Screen Junkies raises during its hilarious “Honest Trailers” clip for Captain America: The Winter Soldier. Like most people, the Junkies liked the movie, but as they put it, they do a comedy series, so they have to engage in some nitpicking.
In this case, most of it has to do with the main through-line of the Marvel Cinematic Universe, which is the idea that Hydra had infiltrated S.H.I.E.L.D. from within. That storyline exploded in theaters in The Winter Soldier and on TV in Agents of S.H.I.E.L.D., though not without some suspension of disbelief along the way.
As the Honest Trailer points out, Tony Stark bragged during The Avengers that it would only take him a few hours to learn all of S.H.I.E.L.D.’s dirty secrets — and the fact that some of its highest ranking agents were working for Hydra would be the dirtiest. Also great: if Hydra had its paws on the Tesseract after it had wormed its way into S.H.I.E.L.D., why didn’t it follow the Red Skull’s original plan and just use it to take over the world? Maybe that would have pushed up its timetable a bit, but come on.
The trailer is also framed by the idea that the first Captain America movie released to lukewarm reception, while The Winter Soldier was almost universally praised. I’m not sure that “He’s Cool Now” tag line is going to be on the Blu-ray when it comes out on September 9, but it sure does ring true.