Sonia Sotomayor had bad timing. If she’d entered college in the late-1950s or early-1960s, she would have been surrounded by an ethos that encouraged smart young ethnic kids to assimilate. If she’d entered Princeton and Yale in the 1980s, her ethnicity and gender would have been mildly interesting traits among the many she might possibly possess.
Leaving aside the likelihood that Sotomayor would have had the opportunity to enter college in the late fifties, note the weaselly phrasing Brooks employs. If she’d “entered college” in the late fifties, early sixties … if she’d “entered Princeton and Yale” in the eighties.
See the thing is, Yale didn’t admit women until 1969. Brooks knows this, but it undercuts his thesis, so he tries to distract the audience with a clumsy rhetorical sleight of hand. And as with a bad magician, the clumsiness becomes more compelling than the illusion he’s attempting to create.