He's so delusional. He really believes he's done a really great job these last two decades and it's just been bad luck that they've managed 3 playoff wins over that stretch.
Most owners, enduring the same run, would immediately question the direction of the club and make changes at the GM level. But when your owner is your GM, you are basically screwed because the owner will never blame or demand the GM change course.
There is zero doubt that he tells himself every August camp that we are ooooohhhhhhh sooo close to a SB championship. And then we spit the bit and he learns zero from it.