I have found and interesting source. Dr Jeremy Taylor at the Department of History, University of Nottingham has a site entitled ‘Enemy of the People’. visual depictions of Chiang Kai-shek. As he points out
Chiang Kai-shek was one of the most caricatured, satirised and lampooned leaders in twentieth-century Asia―if not the world…..Unlike many of his fellow dictators, Chiang is impossible to tie down to one particular event, moment or issue…….. He was an anti-imperialist revolutionary, a wartime leader, a defeated militarist, an anti-communist stalwart, an authoritarian despot, and many other things to many different people.
The site is a bit hard to navigate, but there are a lot of good images in there. Most of them are from the 40’s and later, which is too bad. Here is a nice image of him as an authoritarian from Shanghai manhua. I think I have a few from the “Red Chiang” period as well.