A closer look at the ups and downs of the most important and interesting friendship in the Marvel Cinematic Universe

The summer after James Spader punched the planet with one of its own cities and two summers before scale would once again be unavoidable, Captain America: Civil War, in its final act, refreshingly, caved in on itself. Shout-out my guy Colonel Zemo, who wanted to see an empire fall and knew exactly how to go about toppling it. He wrecked the most important and interesting friendship in the MCU. Avengers: Endgame is going to tie off the obvious loose ends—namely, is Spider-Man permanently dead and can Captain Marvel and Ant-Man do what everyone else couldn’t?— but it’s also going to do some important stuff, like resolve things between Captain America and Iron Man who, during the events of Infinity War, were still not on great terms.

A refresher, then. 2016’s Civil War begins with an Avengers drop team kicking ass in Lagos, on a generic “stop X from falling into the wrong hands” mission. They succeed, but the gang causes some political fallout by blowing up a Wakandan embassy in the process. And, after not saving the world cautiously enough so many times over, this is the final goddamn straw. A U.N. coalition sternly suggests some oversight, and half the team goes along because at the very least it’s good PR. But the question of how long their leash should be, or if they should have one at all, draws battle lines all the way down the roster. On one side is Iron Man, who’s unwittingly created several supervillains by this point and would really like someone else to be responsible for the decisions for a change. On the other is Captain America, who still thinks it’s best and safest for the Avengers to remain accountable solely to themselves. One of these stances, as Sean Fennessey noted when we were talking about Avengers: Age of Ultron last week, sounds much more taxing than the other. How each deals with failure, and the radically different lessons they take from it, inform the two heroes’ relationship: Cap is technically more than 100 years old, but gleaming and perfectly square and powered by a seemingly inexhaustible source of idealism. Stark’s misadventures—and unchecked mental health issues!—have aged him in dog years. That tension guides the plotlines of most Avengers team-ups; it’s why defeating Loki or Ultron or Thanos is infinitely harder than it otherwise would be if they had clarity of purpose and a clear chain of command. Cap wants it one way, Tony wants it the other, and the team, as a whole, suffers for it ad nauseum.

There’s a scene in Civil War where it’s just the two of them in a boardroom, discussing whether or not to sign the Sokovia Accords, which is what the U.N. calls its treaty with the metahumans. They catch up, they jostle over what going legit would mean, and Tony says he’d like to punch Cap “in his perfect teeth.” I mean, look at them here. It’s astonishing that one of these men just chased someone halfway across Berlin on foot while fighting off a SWAT team and the Black Panther. It wasn’t Tony.

They also talk about how Cap was friends with Tony’s father, Howard—you never forget who gave you your first vibranium shield. I’ll just skip straight ahead to the part when we find out that Cap’s other best friend Bucky, who spent the last 50 years working as a Hydra field operative, killed both of Tony’s parents. What’s worse is Cap knew and didn’t say anything, and what’s even worse than that is how he helps Tony work through his grief:

He’s a slippery bastard, that Colonel Zemo. By the end of Civil War, the Avengers are all split up with no one to conquer them. Thanos, obviously, obliged. If you think about it, Infinity War is two and a half hours of twosomes getting their asses beat: Thor and the Hulk, Vision and Scarlet Witch, Black Panther and Captain America, Dr. Strange and Iron Man—everyone ran up, everyone got done up.

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During the events of Avengers: Infinity War, Captain America leads the ground forces against the planetary invasion, and Tony takes the fight to Thanos on Titan. Neither of their plans work; everyone dies anyway. Only a failure so spectacular could get them on the same page: Tony, for all his nanomachines and superbots and contingencies, was powerless to save even Peter Parker. Regardless of how well he stuck to his code, Cap still had to watch half his friends turn to ash.

So that brings us to the final “special look” at Endgame, which chucks the suspense of whether Tony makes it back to Earth or not. Instead, he asks Steve a simple question. “Do you trust me?” “Yes.” They shake hands, and then you’d assume it’s back to Titan to get their asses beat one last time. There’s a scene in Ultron where “Endgame” is first said on the record, in that knowing way that’s obviously setting the table for something. At the time, the Thanos threat was still “that hole in space.” How could the Avengers contend with something like that again? “We’ll lose,” Tony says. “Then we’ll do that together too,” Cap says.

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