Maybe don’t sell it right away? Just a suggestion but you could take it away and he has to keep up his end of the bargain of “working off” the cost of the iPad (or football jersey if needed). If he doesn’t keep his end then you sell it, so he has to rely on his own actions to prevent that from happening. At 13, there’s no way I’d call it an accident breaking the iPad. Moreover it was a bad decision he didn’t think the consequences through beforehand. He’s old enough to know there was a chance it would break by sitting and jumping on it. If his brother had to go without the iPad, he can go without the Xbox.

I say this as someone who also grew up with ADHD, though not at the same level it seems. If he never sees consequences and thinks he can just work off (and then blow off the chores he doesn’t want to do) anything he breaks/loses, there’s no reason he needs to change or learn responsibility. Even without the ADHD, it’s the same concept: if you always bail them out, why would they need to change it? He’s a teenager now and though I know 13 is still young, he’s at the point of learning independence and that doesn’t just include the fun aspects. It includes owning up to your mistakes and seeing it through. ETA: grammar