Theory: McCree was the one who called Ashe to attack the train.
…because he wanted to wake Echo up.Â
And Echo wasn’t supposed to wake up.Â
The diner McCree is having his apple pie and coffee is deserted. Like, there’s no staff in there at all. And there should be.
 Coffee is fresh and steamy, one cup ready to be served… but there’s no one.
The dishes are gathered, but they aren’t exactly dirty; or look like they’ve been in the sink for a very long time.
And the apple pie looks fresh and yummy.
All the above don’t indicate a place that was deserted for a long time. And even if this is a place where there’s simply not much traffic, one has to wonder… where’s the staff?
Did McCree do all this? Brewing the coffee I can buy. Putting on the song in the jukebox I can buy as well. But making the pie, putting it in the glass case, cutting up a piece and serving himself in a seat? No way.
Only explanation I can find (that doesn’t include “budget” or “because I say so”) is that McCree himself drove everyone away with his gun.
And then sat there, eating his pie and waiting for the train.
Because he had called the Deadlock Gang right before that to give them the tip.Â
The tip he refers to here:
“You’ve never been one to shy away from a good tip.”
And Ashe called McCree being there “awful convenient”.Â
So, McCree was the one who set it all up. He called them from the hanging phone, then drew his gun on everyone in the diner to send them away, since he knew that the Deadlock Gang would appear and it’d be dangerous for them. So, he acted like the Bad Guy for their safety.Â
He poured himself a cup of coffee, he sliced some apple pie and waited. Lo and behold, animated short begins.
The answer is simple. He says so himself.
“All I want is that crate.”
Echo. He did all of this to get Echo back.Â
Remember, Echo is Overwatch. Overwatch is outlawed still, even in this time of need. From McCree’s words, “They’re getting the band back together,” Winston has just sent the call and McCree recieved it. And he knew that Echo, for whatever reason, would be extremely useful and needed to Winston and the newly pieced back together Overwatch.Â
But, Overwatch is still illegal. And no one must know that it is getting back together, otherwise the people will be hunted down and arrested, no matter how noble Winston’s intentions are; the law is the law.
So, what is McCree supposed to do now that Overwatch needs help, has called for him specifically, he wants to help, he knows that Echo would be more useful than him and he needs to free her and send her to Winston without him ever be connected to it, because he’s a known ex-Overwatch member? Or, even better, an ex-Blackwatch member, the fraction that supposedly, put Overwatch in trouble in the first place?
How to steal Echo away from the government without linking himself, Overwatch/Blackwatch to it so that he can keep the return of the Overwatch a secret for as long as possible from any government?
Use the Deadlock Gang, of course.
This way, their presence is everywhere in the crime scene, they get the blame and both McCree and his connections to Overwatch/Blackwatch are erased. Echo goes back, he goes to fetch maybe another member in secret.
“Why would he get through so much trouble?”
He cares about Overwatch and believes in its mission, duh.
As for the complex nature of this whole operation… Jesse McCree was Blackwatch. Covert missions. Acting from the shadows, framing others and leaving no traces behind that it was him is exactly what Blackwatch used to do.
And all he’d have to face is the accusations that he pulled a gun to the people in the diner. Maybe. Which wouldn’t be a big deal for him; he’s already an outlaw.Â
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