This is the true High Broderism - not just a belief in the ultimate rightness of the club of bipartisan technocrats, pundits, and other elites, but a belief in their actual power.
While Clintonites have now entered into the ruling class, they weren't there in the 90s. The Wise Old Men hated Clinton in part because he upset the existing social order and forced a lot of their friends to find new jobs (see Travelgate for a trivial example) after 12 years of Republican rule. They had been dancing in a well-orchestrated dance for some time and didn't appreciate it being changed. Then they hated him because he refused to obey their call for him to resign after the Lewinsky revelations. They hated him even more because they recognized how out of touch they were with mainstream public opinion.
The Wise Old Men of Washington believe they run the place. It's their town, after all. They thought Bush would have to listen to them.
...adding, as I left off my final point - so, yes, their failure to understand Bush has to do with their failure to simply listen to Bush the Man instead of Bush the Imagined Man, but I think a big reason for that failure is the belief in their own rightness and power. They are right, they are powerful, so of course Bush should agree, and Bush should listen.