I did this for USNews back when, around the time Speaker of the House Newt Gingrich, American Political Genius Deluxe, gathered his forces and shut down the government in a budget fight with Clinton. Or more likely it's from somewhat later, when Gingrich was out as Speaker and suddenly had some time on his hands to go camping and roast wienies.
He's fun to draw, with that enormous, tetradodecahedral head and that teeny, obnoxious mouth. It's one of the few old caricatures that I'm completely satisfied with (it's now in the private collection of Herblock Prize winner & Pulitzer almost-winner Matt Wuerker). If I was still doing caricatures regularly I'd be jumping around in a fit of joy now that he's considering a run for president. It's pure selfishness, I know. But faces like this are wasted in the private sector.