This is an interesting article about the lawyers in the California lawsuit claiming that the U.S. Constitution requires same sex marriage. Ted Olson (and David Boies) argued that it does. Chuck Cooper argued that it does not.
The article talks a bit about how Olson and Cooper are both conservatives and both headed the Office of Legal Counsel during the Reagan Administration.
I worked for both of these men. I served under Cooper in the Office of Legal Counsel and then worked for Olson at Gibson, Dunn & Crutcher. Both are excellent lawyers and not surprisingly demanding bosses.
The article portrays them differently. Cooper is described as “an unrepentant and avowed originalist” who “believes the letter of the law sticks,” whereas Olson is portrayed as being more pragmatic.
I am not sure that I see it that way. My belief is that Cooper is an originalist who looks to the practices at the time of the enactment as being extremely important, whereas Olson is an originalist who was quicker to find abstract principles in the law that then needed to be applied, even if they conflicted with the practices at the time. This would certainly explain their differing positions in the gay marriage case.
But it also explains other positions that Olson held. For example, if memory serves, Olson was responsible for an OLC position that held that the state enforcement of federal law was problematic because it potentially violated the Appointments Clause. This inferred an abstract principle in the Constitution without specific examples of that principle existing at the time of the Framing. This interpretation of Olson might also explain his innovative work as a private attorney arguing, without significant historical support, that punitive damages violated provisious in the Bill of Rights.