
TBH, i think he kinda deserves it, he's just half-assedly doing things. He needs to be more proactive if he wants to get what he want.
I hope it's not too late for him to pursue Henry, or i hope he'll learn and find a better opportunity with someone else.
At this point, i'm not shipping anyone with Henry hahahaha. I just want them to get out of this messy situation and find happiness.

I wouldn't say he deserves it. No one deserves to lose out on their dream, or to experience heartache. Sam's not a bad person, nor the villain of the story, so to say he deserves to lose everything is somewhat cruel.
He deserves his happiness, too. And honestly, it didn't seem like Sam half-assed baseball. It felt like (and this is entirely speculation) Sam's indifference started after his accident. That makes me wonder why...
As for being more proactive... Sam's only just realized what he feels for Henry is /that/ kind of love. A bit late, but better late than never. Perhaps this marks a decided point in Sam's growth as a character?
As for shipping... Henry is a mess. Sam is just now realizing his /true/ feelings, and Seth seems to be experiencing his first real crush. It's a recipe for disaster and heartbreak for everyone involved. Personally, I dislike Henry the most lol. He's using Seth to run away from his lingering feelings for Sam, and he doesn't have the self-awareness to recognize it. Maybe if he was Seth's age, I could blame it on youth, lol, but come on! He's a grown ass man. I wish he'd act like it.

Not sure if you're talking about Sam, but if so, I agree. He does need to be proactive and do better. Will he? I hope so. But even then I think either relationship would be a mistake at this point. Henry is a mess lol. He's pursuing Seth while running away from his lingering feelings for Sam. It's a recipe for disaster and heartbreak all around. Does Sam need to do some major character growth? Yes! But I think Henry does, too.
Lost baseball, lost the wife, and now he lost Henry. Smh, that man's life has been nothing but losing.