I always thought it'd be really interesting if All Might was jealous of Endeavor, too.
Endeavor' jealous of All Might' status and fame. People rarely recognize all Endeavor has sacrificed to get this far, because why should they? Why should they when All Might is just so much better without even trying? Endeavor envies how flawless All Might always seems to be, from his kindness to his skillset, the gap between them just can't seem to go away.
(Going over why I think it'd be interesting for all might to feel the same way under the cut)
...but All Might isn't 'flawless.' Obviously, no human is. But people forget that's what he is sometimes, who can blame them? All Might can't, he can't blame anyone but himself. But when he finally chooses to look behind him in the race, he can't help the feelings that overcome him regardless of how hard he tries.
Endeavor is human. That is All Might's impression of the man from an outside perspective. Endeavor can be upset, sure, he isnt as popular as All Might. But Endeavor has fans either way, Endeavor has fans because of his ability to show when he's upset. He doesnt need to lie about it. People love Endeavor in a different way from how they love All Might, and All Might knows he can't get that kind of love from them. The kind that recognizes their humanity, that's rare for any hero.
It got even worse whenever he discovered Endeavor had an actual family. All Might didn't know how his wife looked, he didn't know the identity of any of his kids up until meeting Shoto, Endeavor had kept his family safe from prying eyes. That was how he saw it. Endeavor cared about his family, and was able to keep them safe.
He didn't have to worry about them being taken from him. He didn't have to worry about them being killed for simply being close to him.
All Might doesnt have a family, none. His father is mysteriously missing (95% chance he' a rotting corpse), his mother was killed around when he was a teenager, and he had to witness the same thing happen to his mentor.
He's come to the conclusion that if he were to have any family of his own, they would be killed. He barely even trusted himself to keep what little friends he has safe, keeping them an arm's distance.
So when he saw Endeavor, hell not only Endeavor, when he heard Endeavor mention a wife, four children...he couldnt help it, really. He wanted to have that for himself, but he knew he never could.
Sorry for the ramble I like just woke up this has been on my mind for a billion years.
