I like to pretend that Jack kept Gabriel’s beanie after the fall of Overwatch. Maybe he took it from him after he woke up from the explosion and found Gabe dead beside him. Jack knew from that moment on that a part of him died with Gabe so he took something, anything (that stupid beanie) with him to feel like he could take something of Gabriel’s too.
I like to think that some nights, when it was cold and dark, when he was alone, when he was more Soldier: 76 than Jack Morrison, that he would feel in his pocket for the beanie and take it out, holding it in his hand, trying to remember every line and dip of Gabriel’s face. The way the beanie shaped around his head perfectly. I sometimes think Jack might even smell the inside, thinking he can still get a whiff of the way Gabe’s skin and hair used to smell.
And, when they eventually meet again, when Gabe is more Reaper than Gabriel Reyes, the beanie falls out of Jack’s pocket mid-fight, just as Reaper is about to lower one of those guns to the old man’s head. When he sees it, Gabe stops. He forgot about the beanie. He forgot how Jack used to like to pull it down over his eyes when Gabe was in a bad mood and Jack wanted to cheer him up. Forgot how sometimes he’d forget to take it off before they’d have sex, forgot the way Jack’s fingers felt gripping the back of it tightly whenever they kissed.
When Jack looks up, and Reaper is gone, he knows that maybe, just maybe, there was a part of Reyes that still lived on beneath that mask. And maybe, just maybe, that part of him still loved Jack.