A wealthy libertarian is bankrolling a challenge to D.C.’s gun regulations—the most restrictive in the country. What drives him—and his take on whether the case will go to the Supreme Court. The District of Columbia has the most restrictive gun laws in the country. But that’s a distinction the nation’s capital will soon lose—if Robert Levy prevails. Levy was born in Washington, but left years ago; a resident of Naples, Fla., who made a fortune as an investment analyst, he is now a senior fellow in constitutional studies at the libertarian Cato Institute. A critic of what he sees as...