He's just incredibly awful. Buckley, Safire, and O'Rourke could write even though their politics sucked.
They also had something to say. They held an ideology, as awful as it often was, that they were willing to defend. TCW just wags his finger at people with actual principles. He's like Bill Maher. He thinks it's a sign of intelligence to be able to both sides all issues.
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And like Maher, TCW fits Mr. G from Dorothy Thompson's "Who Goes Nazi." He'll never officially go Nazi, but he'll happily defend then as an intellectual exercise.
Who Went Nazi?
The More Things Change…
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Safire anyway.