But the latest potential addition to Trump's team could take things in a totally different — and more disciplined — direction.
This doesn't seem to be a done deal. Olson has turned Trump down before, and he declined to comment to The Post. But he is reportedly going so far as to review potential conflicts of interest with his other casework, which suggests it's a real possibility.
Olson's name will be more familiar to readers than any member of Trump's existing legal team before they joined, including Ty Cobb. Olson served as solicitor general in the George W. Bush administration after representing Bush at the Supreme Court in the monumental Bush v. Gore case that delivered the 2000 presidential election to Bush.
He was even rumored is a potential Supreme Court pick on two occasions, but was selected neither time. By the tail end of the Bush administration, he was such a lightning rod that Bush passed him over for attorney general, instead selecting Michael Mukasey.
Before that, Olson had built a career as a conservative legal activist, advising Paula Jones's legal team in its lawsuit against President Bill Clinton and defending special prosecutor Kenneth Starr in his investigation of Clinton. Olson attacked Attorney General Janet Reno's Justice Department during Clinton's administration, accusing it of being politically corrupt. He often sued the federal government to soften regulations on the environment, affirmative action and sex discrimination.
But a decade ago, he broke with conservatives by working to overturn California's same-sex-marriage ban, Proposition 8, which was chronicled in the documentary “The Case Against 8.” In that case, Olson actually teamed up with his opponent from Bush v. Gore, David Boies.
“This is the most important thing we’ve done in our lives,” Olson said in 2012. “It’s not just become a legal challenge, but it’s about the hearts and minds of a country changing.”
When the Supreme Court legalized gay marriage nationwide in 2015, Olson declared, “I can’t even begin to describe how good I feel for the people whose lives are affected in a good way.”
On a personal level, Olson was perhaps the most high-profile Washington official to lose a loved one in the Sept. 11, 2001, terrorist attacks. Olson's wife, conservative commentator Barbara Olson, was in the plane that crashed into the Pentagon. He reflected on the 10th anniversary of that day: “When I appeared in public, I had to stress that I’m not unique. ... Unfortunate, tragic things happen to all of us. It’s very important to put that in perspective: You’re not the only one that has experienced a terrible tragedy, as thousands of other people did that day.”