Ages: Both 69
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The two attorneys fought on opposite sides of the Bush v. Gore case in the Supreme Court in 2000, with Olson representing the winner. But last year, the odd couple joined forces to bring a lawsuit against Proposition 8, the 2008 California referendum that ended equal marriage rights in the state for gay couples. Bringing the case, which is pending, was bold but risky: if it ends up in the Supreme Court, the conservative Justices may vote to end equal marriage rights in every state. Still, Olson's collaboration with Boies is a sign that some conservatives are moving on the issue.