This was a good post, and thought-provoking.
I tried to imagine Haskins was some white dude QB and the same statement about struggling to find his purchase in the NFL and decided it was acceptable media context. It left the door open for complaint, but it was just a typical 'hard edge' fact that one can easily exculpate or even appreciate from a journalist.
The context is especially useful if there are factual bits (e.g., Haskins was partying until late in the night, struggling to master an addiction of some form related to his perceived lack of NFL success) that subtly inform us of a morality play at hand.
The conclusion I come to is that someone like Shefter has no obligation to sugar coat his message, but his reputation will hinge on the accuracy of the tone as more details emerge. If this was a pointless tragedy, it will tarnish his reputation. At this point, knowing what we know, it's hard to really fault him much. Running across an interstate is a bad idea, it requires explanation.
Having said all that, it is tragic no matter what, and my heart goes out to the extent it does anyone I've never met who dies too young and leaves behind sadness of those who loved him or her--parents, family, friends.