Boies beat Microsoft when he was in the Attorney General's office, but other than that his carrer has been marked by high profile losses. He's just intelligent enough to pick losers with fat pocketbooks.
In case anyone else missed the association, this guy was Al Gore's lawyer in the 2000 race, and the guy who argued that the votes should be recounted until Gore won. He also represented Fastow from Enron fame, tried to defend Napster as a legitimate business, and works for SCO in their ill-fated attempts to sue Linux out of existence. This guy has a penchant for choosing the losing side (even his win agains MS was mostly overturned on appeal).