hepcat
Former PH, USN
What happens in the streets is largely random. I don't see how you can make candid photographs without randomness affecting your work.
On the other hand when I watch videos of GW working in NYC, my impression is his photography is focused and purposeful.
While you're at the mercy of random events happening in front ot you, it's your choice which of them to photograph which is not, of course, random. However, shooting as he was filmed shooting there often is no attempt to change from his eye-view height, or move for better framing to include or exclude elements. I've seen him move to chase a subject, but not to re-frame or give or remove context. So what you get is what he saw from where he stood with his eye level angle, distractions and all.
If, however, the only thing you choose to photograph on the street is attractive young women (and there's nothing inherently wrong with that) then your body of work begins to take on a completely different appearance and meaning. To tie this back into the OP's post and the opinion piece it references, I think it's hard, in the totality of the sheer volume and array of Winogrand's body of work, to pigeonhole him or try to suggest that there's anything unifying like that. If anything, it was the exhibit's curator who chose specific images out of thousands who chose to make a statement about what he or she thought was important.
Again, I'm not a fan of his style, but I admire the legacy of his body of work and what it represents.