Henry Schmidt hat
Thanks to Rob (Fballguy), I was able to track down this item, listed as an LA Rams related item. It belonged to the Rams/49ers/Santa Clara University trainer, Henry Schmidt. It has signatures from Tom Fears, Norm Van Brocklin, and Elroy Hirsch. But, more importantly for me, it clearly started during the Santa Clara University 1949 season, which ended with an Orange Bowl victory over Bear Bryant's Kentucky team. Unfortunately, Bryant did not sign the hat. I always heard that he was pretty pissed about this loss, and never wanted to talk about it.
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