Garry Winogrand (1928-1984) was a pioneer of American street photography. This study of the man and his work follows Winogrand from his Bronx birthplace to Manhattan of the 1950’s and 1960’s, observing private and public moments, witnessing history. Winogrand wasn’t just shooting -- he talked endlessly about what he did with light and with his subjects, and about anything else. But his life took a turn when he left New York for Texas, and then for California, eventually leaving thousands of rolls of film undeveloped when he died. His legacy pivots into a mystery, which director Sasha Waters Freyer explores. We’re left with a wealth of images, and with fellow photographers struggling to explain why Winogrand shot them.