Praise of the man:
"The one talent of David's that stands out is his ability to lay out a course of action that would take into account any sort of complicated facts and develop a far-reaching scenario. It's a chess player's sense: If I do this, the following 15 things are going to happen, and if step 11 goes so, I'll do this rather than that. It's a fantastic game-playing ability." Thomas D. Barr, quoted in the New York Times Sunday Magazine, June 1, 1986
"The Boies memory is one of the first things cited when people discuss his strengths. What's most impressive about that gift -- focused as it may be by the intensified concentration that his dyslexia demands -- is Boies' uncanny ability to recall a key fact, legal citation or piece of contradictory testimony at moments of the most intense pressure." Time Magazine, "Get me Boies!" by Daniel Okrent, December 25, 2000
Boies can grab enough of the subject matter to speak to the key legal issues, and to ask experts the questions that define the boundaries around those questions. Another lawyer might know more of the subject matter, but that won't matter if they can't translate that extra knowledge into legal strategy.
Remember also that while you might be able to find legally pertinent technical responses to Boies' work in court, you're reacting to that after hearing his strategy. Good trial communication requires telling a unified narrative -- if your story doesn't already provide a basis for your response, that response will be weaker and may even distract from the story you do have. Boies' ability to anticipate arguments, mentioned by another comment, is crucial to all this -- it's not enough to have an answer, you really need to have that answer in advance of his question.
As a former litigator turned startup founder, I can attest to the difficulty of assembling the right team with the ideal point man for a trial, and when you do find one you respect, he is worth every penny. David Boies is one such man - nobody has gotten fired for hiring him as the lead trial attorney.
(IANAL but I helped AOL sue Sanford Wallace, and it was a sight to behold.)
David Boies has argued in Bush v Gore, defended Napster, worked for SCO in SCO v Linux, argued the recent California gay marriage law, was the council for US team in the recent America's cup case, and now he's Oracle's lawyer here (at least I see the last connection).
I can't discern a pattern to those cases other than their high profile nature. Wouldn't it make more sense to hire someone that is an expert in computer IP law for SCO, Oracle, Napster type cases, a constitutional lawyer for the Gay marriage and Gore v Bush type cases, etc. How can one guy be the go-to for so many high profile cases?