(based on this. Big thanks to @m4ycrowave for the inspiration)
Phil had said for so long that they must have done something truly awful in another life for their lives to go to shit all at once like this.
Mum had gotten sick even before she'd had Tommy, and the cost of keeping her comfortable on only her husband's paycheck was unsustainable really. She lived long enough for the family to have hope for her recovery, but those hopes were dashed when Tommy was 7 and the hospital treatments couldn't keep her heart going any longer. Phil knew they couldn't keep the house so the four of them moved into a flat in the city after that, but with the market as it was they still lost money in the sale. When his work was destroyed in a clash of heroes and villains, he worried they'd lose their new home, too.
Phil wasn't naturally gifted in fighting or mechanics or any of that, but he'd seen that anyone who got into the hero business would be supported at least enough to live, and really, they owed him for taking away his family's source of income. He was able-bodied and determined, so with training he was let in, first only assisting the smaller heroes, but soon proving himself to be a "level-headed asset with innate leadership abilities" (Tommy had read that in a letter his dad left on the table once). The organization recognized the man's use, and though overworked, Phil would be able to keep his remaining family off the streets.
Techno, in comparison, was talented in the blade. He joined just as Phil was gaining respect in the industry, before he could say anything against it. It was easy to tell Techno would go places, with his natural fighting sense and ability to separate his feelings from the job.
Though here's where Phil's belief in their horrible luck seems to hold some weight: Wilbur had apparently been participating in their new occupation as well, though without telling his father or brother at all. One night, Phil received a call, grabbed his keys, and ran out the door. He didn't return 'till morning and when he did he looked so exhausted Tommy couldn't even ask what had happened. He learned later that his brother, the one who'd stayed with him when Mum had gone and when his father and brother had gotten so busy, who'd just played President and Vice President with Tommy after he'd learned about government in class, who'd been struggling in his own classes recently but made Tommy promise not to tell...
His oldest brother had gone out in secret and talked himself into a job with the organization and gotten himself shot or stabbed or something. By the time Tommy knew about it,they already knew Wil was going to live, but he'd never be entirely the same. From then on, Phil told Tommy he had to be careful what he talked about with Wil or he might get all floaty again. Tommy's seen it, where he'd lose the edge in his gaze and in his voice, and his mind seemed to float way up above everything they normally had to worry about. Tommy thought that maybe it was a good thing he let go every once in a while. Phil insisted it wasn't.
By the time Techno and Phil finally realized they couldn't stop Wilbur from following in their footsteps (he'd always been the more idealistic of the three), Tommy was 12. Old enough then to realize his family was gone a little more often than they probably should be with a 12-year-old at home.
Now, he's nearly 17. That's old enough to realize Phil was wrong. They'd never done anything to deserve all the shit they'd gone through. But if it were going to keep happening anyway, maybe he could do a little something to deserve it a bit more.
What was that Wil had been saying about none of the villains these days being worth chasing?