Is a stock buyback guaranteed to increase market cap?

Alternative form of the question: Is it always possible for a corporation to use it's insider knowledge to time its stock buybacks so as to increase its own market cap? And if so, why isn't that an illegal form of creating fake value?

I can understand that fewer shares reduce the supply and increase the stock market price, but what is really going on there?

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long story short, cancer conservatism killed them off…

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