There's no crying in the apocalypse; water is too valuable a commodity to be wasted on tears and sorrow. He'd learned that lesson pretty quick. That dead future-world didn't care how scared or lonely or tired he was. It didn't care that he was just a boy (the boy, the only one left). It was indifferent to his sorrow and suffering, and so Five became indifferent as well. He buried his siblings, the rocks on their bodies too heavy to move and so he added more, covering over their dead faces and then he left them there in the smoking ruin of his childhood and walked away, out into hell.
He tried to get home so many times.
But it was harder to go back than forwards. Forward was limitless; endless possibility. Back...back required a level of skill he just didn't have. Back required complex quantum equations that his shell-shocked, grief-stricken mind simply couldn't comprehend. Back had happened and he couldn't just slip in anywhere. He doesn't know why he didn't consider that when he first jumped. Well, he'd been young and stupid after all.
It was a stupidity he paid for dearly.
The first couple months were the worst, and the first couple years after that. Back before the numbness set in completely. Back when hope was still a pile of glass shards in the pit of his stomach, grinding painfully.
Or maybe that was just the remains of his heart.
For all that, he didn't actually consider suicide all that much. Whenever he did he'd remind himself that the world depended on him, needed him. Only he knew what was going to happen. Only he could stop the apocalypse, keep the world from burning. Save his family. He couldn't save anyone if he was dead. It was the thought he clung to and it was enough to keep him going. It was still terribly lonely though and he's sure he'd have gone insane without Dolores there to talk to.
She's the one who suggested he try jumping into the future again.
She was so smart, his Dolores (he took her with him of course). He made several jumps into the future and what he discovered gave him the faintest hope. Humanity never recovered but the earth did, in a sense. He jumped to a time when the world was no longer on fire, when the stench of dead bodies had long dissipated and growing things began to cover over the scars of the apocalypse. He jumped to a time when there were trees again.
He made his home there, in that tenuous return to life. There were no animals anymore so he stayed in the ruins of the city, his best option for food and water and alcohol (the rivers were still polluted with a heavy sulfur taste that made him ill and which boiling did nothing to abate). He settled in the old library, digging up books about quantum physics and probability and anything, anything that might help him get home. When he wasn't scavenging for food he was scrawling equations on every surface he could find, his handwriting growing cramped and uneven as the years took their toll on his body. The equations growing longer and more disjointed as the isolation took it's toll on his mind. By the time the Commission found him (by the time they let him know he'd been found) he was probably more than a little crazy. He'd never admit it of course, but he could tell by the way Dolores looked at him sometimes she thought his mind was slipping.
Well, it was a hard-knock life.
He went to work for the Commission because it's not like he was going to get a better job offer. They pulled him out of time, cleaned him up and after a 'readjustment' period where he got used to doing things like sleeping in a bed and using silverware and not startling whenever someone got too close, they sent him out on his first mission. It was harder not to get lost in the sounds of the city than it was to pull the trigger.
Turns out being numb and angry made him a very effective assassin.
They went easy on him at first, simple missions with easily discovered targets. No one famous, nothing complex. They were surprisingly careful with how much exposure he got to the living world before he took someone out of it. It was hard at first, what with the people and the noise and the sheer amount of busy. He struggled to stay focused, not get distracted by little things like birds. (In his defense, he hadn't seen a bird in forty years.) It got better though, a little at a time. Eventually he could stand on a city street and watch humanity rush by him without feeling panicked.
Eventually the nightmares started to fade.
He liked working alone. People got in his way, got on his nerves. He'd acclimated to their presence but he wasn't used to them. Wasn't used to being looked at or spoken to by anyone other than Dolores. They paired him up the first couple of times, more for observation than anything else. Once they were sure he could handle being back in civilization they started sending him on solo missions that would normally require two or even three agents working in tandem, and that was fine with him. A partner only slowed him down.
Teleportation had it's advantages when you needed to kill three people at once.
So, he was good. He was very, very good. Forty years of isolation had removed him from humanity enough he didn't feel remorse. Decades of hard choices gave him a cynical, pragmatic view of the world. A lifetime of struggling to survive had made him cold and untouchable. What did it matter if he killed a dozen people, or two dozen, or a hundred?
It all ended in flames anyway.
He was in Dallas, taking aim at his latest target when he had an epiphany. He'd been running calculations in his head, adjusting for distance, wind resistance, gravity...all the factors in play when sending a bullet over long distances. He was about to pull the trigger and not thinking about time travel at all when the equation came out of nowhere. Dolores had always told him his math was wrong and he had to admit she'd been right. With shaking hands he flipped though his book, the one where he kept the most promising research and there it was, clear as the sky over his head. It would take only a few minor adjustments to make it work.
Sometimes it takes a lack of focus to bring things into clarity.
He didn't even think about finishing his contract, not after he'd already waited so long. If he was successful, that future wouldn't even exist. He'd never be in that ruined city to be found by the Handler. The city wouldn't be ruined in the first place. He could stop the apocalypse, save the world, his family...himself. He made the jump right there, tearing a hole in the fabric of the universe and pushing himself through to the other side.
The old man was wrong about one thing; falling back through time wasn't like falling through ice.
It was like being crushed down to the size of an atom and then expanded again, all at once. It was hard and it was painful and he hoped like hell he didn't ever have to do it again. But Five had long become indifferent to pain. It didn't matter, didn't mean anything. The body's response to damage, nothing more. Fix the damage, ignore the pain, move on. Survive.
The world didn't care about his suffering, so neither did he.
His family had only changed for the worse. They'd always been an odd bunch, held together mostly by their father's authoritarian nature and the shared experience of being miserable under the same roof. But that was a glue that weakened over time, and when Ben died the heart went out of the Umbrella Academy. He got caught up on the details through Vanya's writing, her autobiography ripping the dressing off all the old wounds, laying everything bare. But it prepared him for what he'd find, the mess their father's wreckage had left behind.
All in all, Vanya's scathing remarks had been remarkably accurate.
The reunion is fairly unemotional. They're all too stunned and stunted and damaged in their own ways to react with anything approaching normalcy, and that's fine because he's not much better. When he was a boy he'd dream about going home, fantasize about the hugs and the smiles, imagine his siblings gathering close around him, relief in their voices as they laughed and touched and cried. But he's not that boy anymore, even if he looks like it.
That boy died in the apocalypse, just like everyone else.
So he greets them with sardonic aloofness, his words as fast and piercing as the bullets he fires. He doesn't let them get close because there's nothing left to get close to. It was all burned away long ago, and all that's left is Purpose. If they're not going to help him achieve it, they can get the hell out of his way. He's too old for their bullshit, to tired for their games and too busy for their questions. He's got eight days to un-fuck the world.
Partners only slow him down.
There are other reasons, of course. He needs to figure out what happened and why, needs to understand the sequence of events before he draws everyone else into it. He needs to make sure what happened then doesn't happen now. If he tells them everything the best thing that can happen is they won't believe him. The worst thing is that they will. They will and they'll involve themselves before he's ready, before he understands. They'll go sticking their awkward, self-absorbed feet into the thing and probably fuck everything up the way they always do and Five doesn't have time to stop and clean up their messes. The clock is ticking and the bomb is about to go off.
He needs to figure out which wires to cut before he starts handing out safety scissors to the preschoolers.
Then of course there's the small matter of the contract on his life and the assassins who are doing their best to fulfill it. The Commission has endless resources, endless bodies they can throw at him. He can protect himself and work on stopping the apocalypse at the same time, but not if he has to protect all of them too. Not if he has to worry about them becoming tangled up in the changing timeline and possibly getting noticed by the Commission. Cha-Cha and Hazel are ruthless and will kill anyone who gets between them and himself anyway, so he makes sure that doesn't happen. He keeps them out of it, keeps them isolated. Leads Cha-Cha and Hazel on a merry chase because if he kills them the Commission will only send more, and more and more and it's better to know thy enemy.
For all of that, he wishes to God he wasn't stuck in the body of a thirteen year old boy. The same stupid kid who thought he could jump through time without consequence. The one who's limbs are so much smaller and weaker than he's used to (it takes some effort to strangle a man these days). There might not have been much left of him at fifty-eight but at least he wore the years on his face, and the scars on his body. He hates that people's first assumption of him is that he's as young and reckless as he once was. Hates that his years and experience mean nothing to them, not even the vague overtures of respect that are due someone his age. If he looked fifty-eight, his siblings wouldn't be falling over themselves trying to 'protect' him. Wouldn't constantly be getting in his way and inadvertently drawing targets on their backs.
If he looked fifty-eight, he could buy his own damn alcohol.
But what did any of that matter, really. The apocalypse was coming and he doesn't know how to stop it. He doesn't know how to pay the debt he owes to himself. Doesn't know how to save the world, that thirteen year old boy or the family he'd loved.
And ain't that a kick in the head.