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and towering ceilings in the conference room. Parker looked hopelessly uncomfortable in his suit and tie. “I said about five words and handed him a check,” Parker said.

With the retainer, Greenstein drafted a twenty-seven-page memo spelling out what Napster’s arguments should be. In what would become an almost-biblical text for Napster’s inexperienced leaders, he revisited the cases Grosfeld had, pointing out a number of defenses. First, he said that in the flea-market case and others, courts had ruled that the companies were aiding infringement when they had direct knowledge of what was happening. Napster, on the other hand, could argue that since the files being sought by its users were not marked either as copyrighted or otherwise, it didn’t know what was in violation. “When you look at cases that impose contributory or vicarious liability in the case of a service, it’s because in those cases the defendant was actually able to exercise present control,” Greenstein said. “For example, someone says, ‘Make a copy’ and hands a tape to someone to duplicate. That person is liable because they could see if it was suspicious. When you’re looking at a service that consists of an automatic, technical process, that’s quite different.” In his memo, Greenstein wrote: “MP3 lacks any flags or other means that indicate whether copyright has been asserted over the music file and whether the music file may be copied with or without restriction.”

Fanning would trot out Greenstein to explain the legal defenses, often by phone, for Draper Atlantic and other potential investors. But he didn’t brag about two other points that Greenstein said he made orally. The first was that, as Greenstein saw it, the odds of a lawsuit being filed against Napster were about 98 percent. The second was that copyright law is a complex animal, especially when it comes to issues on the edge. Those are “the grayest of the gray areas in the law,” Greenstein said. Sampling of older songs in rap music was one such battleground, a fight between fair use and infringement. The significance of the trend for Napster was that the eventual lawsuit was bound to be what lawyers call “fact-intensive.” The ultimate ruling would almost certainly turn on Napster’s internal conduct, the evidence produced from within about what it knew, what it should have known, and what it could have done about it. For instance, a court might inquire whether Napster’s servers had the ability