>>13548825>>13548850He books them so people look back on his era more fondly, including the Reign of Terror. Thats the reason Roman's pushed as a neverending dominant but also cowardly inept always-needs-help heel, the reason the faces are choke artists or crossdressers, the reason there's so many manlets.
HHH sees himself in Gunther, the 'great wrestler' workhorse who held the midcard together for years before he got a shot, because HHH is a narcissist. Every other push he gives is to make people go "Fuck, this sucks, I miss the Reign of Terror in comparison"