True: hiring non-programmers from top schools and then giving them tasks like "fake out multifinder enough that WinHelp runs" is a unique form of cruelty. But most work in the 1990s was like that. He should be glad he landed at Microsoft instead of Commodore or 3DO or half a dozen other places.

Stack ranking will do that too you, its like working in 1940 era USSR

You could still take the fat salary until they found out it's not working (because, of course, it cannot possibly work). If they decided the code base is too crufty (instead of deeming you incompetent) you could still keep the fat salary and land in another realm of the company. Unfortunately for you, the odds of them deciding the codebase is too crufty (and, therefore, that the very senior exec sitting on it managed its aging poorly) are not good.