1. The dude watches basketball, I think that's clear.
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3. Simmons mentioned in the podcast and MVP article that he has watched all or almost all of the Celtics games this year. I see no reason not to believe that.
Yes, I believe Simmons watches the games. Whether he pays attention, though, is up for debate.
I mean, how do you rationalize the "Ray Allen is just a spot-up shooter who doesn't play defense" line of reasoning? Anybody who has followed Ray at all this season knows that that's far from being accurate, and you would expect Boston Superfan #1 to recognize that.