How do we understand artists that lend their work, even their entire living, do less-than-honorable organizations, governments (etc)? Further, what if the artist knowingly supporting these corrupt institutions are aware and even detest the institutions themselves.

Well, I suppose that particular artist has a lot to work out. In the case of Shastockovich he created some very wrestling works throughout the 20th century despite his moral ambiguity.

Above is an example of a particularly moving Shastockovich piece made to lament "the Great Battle" when the Germans invaded.