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Huh, I just checked my Tex and his hat and it seems I have the same problem
My Tex's hat is also really difficult to take on an off. I wonder if it has to do with the shape of the plastic compared to the others? Chief's hat slides on super easy and fits loose, it moves around on his head but his ears hold it in on his head. 4-Speed's is tight putting on but then fits pretty nicely nicely, not as loose as Chief's though.
Same problem. Now i never put the hat on my Tex and made a replacement one out of silicone. I can't let him without his hat!
Maybe over the years the plastic has formed differently. I think the hat was originally made to stay on. But when taken off, the plastic had more space to "relax" and expand to a degree.