The confusion, I think, is partly because Brooks didn’t really explain his concept — at least, he didn’t explain what ESPN has to do with Obama’s masculinity or ability to connect. I will attempt to do so (with the caveat that I can’t know exactly what Brooks meant).
Think of the symbolic activities that have defined men in the past. A manly man (where I’m from, at least) might hunt, fish, drink, drive fast cars (sometimes while drinking), play contact sports, etc.
Now think of the opposite of that: There are plenty of straight men who eschew almost all the traditional trappings of macho-ness; they’d rather go to the theater than watch a ball game. They’d rather dine at a nice restaurant than grab a beer at a dive.
Obama represents a middle ground.
He is urban, so hunting isn’t really his thing. He is serious and disciplined, so he probably doesn’t drink a lot or engage in other risky behavior.
But he’s also not the kind of guy who would rather go to the ballet than watch the Red Sox play the Yankees. His love (and knowledge) of sports is more than enough to get his dude card stamped. He can hold a conversation about RG3 at a bar in Georgetown if he needed to — and that’s more than you could say for a lot of guys now days.
Obama represents a cosmopolitan sort of manliness. As more people move to the cities, it is, I suspect, a growing demographic.