Photography was available when he was famous, and he most probably taken picture, the question is moot, he's an artist, and his tools are reflexions and ideas. Photoshop is only a tool for executing task not to think at all.
As an artist he'd find some other way to express himself . I have little idea of his commercial aspects. HCB lived long enough to change his medium of expression. Copying the past greats is a tribute to them. But sad in a way for the copyist, too.
Actually, I think that dabbling was minimal. According to his friend David Douglas Duncan, Picasso once pointed expressed disdain for photography, pointing his brush at Duncan's lens and saying, "The trouble is here!"
Duncan responded by having a lens/prism system custom made and published the results in his book Prismatics: Exploring a New World.
One of my good friends is a graphic artist and loves to simply draw, resisting any attempts to 'modernize' his process. He enjoys photography and shoots almost everything on Program mode because he finds technology distracting. I used to say I might get one keeper from a roll of 36 but he'd often get 36 interesting shots because of his artistic ability.
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