Which are of law would a history major feel most comfortable specializing if he were to go to law school?

Answer 1

Constitutional law. Most others never research anything back more than a few years, because there is no need. It is only when dealing with fundamental Constitutional issues that you delve deeply into the history of a law.

Good luck. It is a fascinating study, especially for a Libertarian, or anyone who believes the Constitution is a sacred contract of We, the People.