Shapiro is not an engager, he’s a debater, pure and simple. It’s a pretty great exercise to dissect his statements, particularly when Shapiro himself puts a lot of stock on starting an idea from something empirical (regardless where it ends up though).
But I have to say that dissection doesn’t seem fruitful when it ends up with a label of “callous”. Really? Yes, his statement about Trayvon is callous but beyond that … ? Shapiro isn’t a lawman and public opinion statements aren’t restricted to how well they’re supported by a legal decision. The court may find evidence inconclusive as a whole to establish a verdict or may end up issuing a verdict on technical grounds outside of evidence altogether.
And you can always boil things down to common sense. In a case with a clear timeline of escalation, wouldn’t you have reason to claim that had the first escalation to physical violence not occurred then the outcome may have been radically different? That is, assuming you do subscribe to the idea that no amount of verbal provocation justifies escalation to physical violence.