For Theodore Olson, the turning point in the case of Citizens United v. Federal Election Commission, the moment when he thought a big win was possible, came during the first oral argument on March 24 last year.

That was when his adversary, Deputy Solicitor General Malcolm Stewart, under duress acknowledged that yes, a corporation-sponsored book could be banned under federal law if it contained text for or against a candidate’s election. Justices were slack-jawed. They ordered a re-argument for September and, on Jan. 21, struck down the law and the precedents that supported it.

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