In 2009, he joined together with President Clinton's former attorney David Boies, who was also his opposing counsel in "Bush v. Gore", to bring a federal lawsuit, "Perry v. Schwarzenegger", challenging Proposition 8, a California state constitutional amendment banning same-sex marriage. His work on the lawsuit earned him a place among the Time 100's greatest thinkers. In 2011, Olson and David Boies were awarded the ABA Medal, the highest award of the American Bar Association. In 2014, Olson received the Golden Plate Award of the American Academy of Achievement presented by Awards Council member Brendan V. Sullivan, Jr.