In my experience, it's always been down to what that person values. At my last company my "boss" was a contractor, and although he was given the ability to build a team however he saw fit, he didn't want to sacrifice his freedom. Before that, my CTO took the role because she believed in the team and the projects we had - and we did some fantastic work. The roles were almost identical, but the people were different.
My hiring experience is limited to developers, so I've never been a part of the actual hiring process, but I've bonded with a handful of people that were offered the role, and it's always been down to belief in the long-term vision and whether they'd value that role over what they value from their current role as a contractor.