As Google evolved from being an endearing startup to an internet empire, the company has become used to critics depicting it as a copyright scofflaw and pushy monopolist. It’s different when the unflattering portrait is being drawn by a federal judge.

This week’s ruling from U.S. Circuit Judge Denny Chin did more than complicate Google’s efforts to make digital copies of the world’s 130 million books and possibly sell them through an online book store that it opened last year. It also touched upon antitrust, copyright, and privacy issues that are threatening to handcuff Google as it tries to build upon its dominance in internet search to muscle into new markets.