I have, for myself, found it sometimes difficult to understand Winogrand and to understand some or even most of his photography.
Just recently, I've decided that I don't even have to like his photographs to like his point of view. However (just to mix things up) I like plenty of his photos, and I'm not completely sure of his point of view.
My view on this is to take a possibly dim-witted and simplistic approach to his struggle between photographer and subject:
If the primary reason for liking the photograph is the subject, then the subject has "won" and the photographer (ie. me) has lost;
If the photograph shows the subject in a substantially better context than it would have appeared in a "straight, for the record" shot then the photographer has "won".
Winogrand seems to have seen photography as this contest. I don't think I'm a good enough photographer to pick that fight - the subject would win too often! Especially so in the wildlife photography that I love, but which I think most likely would have driven Winogrand spare.
In this day and age, IMO, that's best done with a dSLR and a very long lens. And, also, why I don't show those photos much at all around here. Its a mode of photography that's most unsuited to RF cameras and seems entirely antethical to Winogrand's approach. (I enjoy it, and I think RFF has taught me a few things that help in this most foreign of photographic worlds.)
And yet I try to like and understand Winogrand. I think I make progress, but I'm not taking this seriously enough that I'd die in a ditch over the probable outcome. Mostly because I can calculate that probable outcome 🙁
...Mike