PhillyGuy - You are mixing up crony capitalism with communism. And the current crop of communists in crony capitalism clothing these days infesting Beijing.
No historian or any players at the time have ever accused the Generalissimo of being either a democrat or a free market proponent. It is true that Wellesley educated Missimo woo’d congress and media giant Henry Luce. But it was “we know he’s a bastard, but he’s our bastard” type faustian bargain. And clearly at that time the US was not going to support Mao and the communists.
And the US was fully aware of Generalissimo Cash My Check. The whole deal was to keep CKS from making peace with the Japanese, thus freeing up forces in the Pacific. Good ol’ CKS avoided fighting the Japanese when they took over Manchuria in 1931, the Xi’an Incident in 1936 and clearly from the Marco Polo Bridge Incident in 1937. Peanut Head was clearly focused on the civil war rather than the Japanese.
Read Stillwell and the American Experience in China for many of the gory details. And just for fun, here’s a link to Stillwell’s poetic ode to CKS: Joseph Stilwell - Burma - Disagreements With Chiang and The Allies | Disagreements Chiang Allies (liquisearch.com)