After learning earlier about Sam Altman's long-con at Reddit, I'm surprised I haven't seen anyone suggest that Emmett Shear accepted the job in order to help get Sam back into the company.

They were both members of the inaugural class of Y-Combinator, and all of Shear's published actions since accepting the role (like demanding evidence of Sam' wrongdoing) seem to have helped Sam return to his role.

I don't think it's a stretch to say that he did win, in that he might have accomplished exactly what he wanted when he accepted the role.