Hardcore neocon Jennifer Rubin explains that despite his name recognition and ability to raise money, he faces these obstacles:
First, he's his own worst enemy, a gaffe-maker of epic proportions. He will seize on a bit of data or an odd theory (as he did on Obama's alleged "Keynian, anti-colonial" world view) and create a firestorm. Sarah Palin's verbal miscues may be more frequent, but Gingrich's are often more egregious. At a time when the public is arguably looking for a grown-up and a sober-minded leader, Gingrich projects instability and unpredictability. Second, he was a terrible speaker of the House.
Bill Clinton outfoxed him. He was a gadfly and a distraction, and virtually every House Republican who is still in Congress who went through that period has very negative memories. This isn't to say that Republican congressmen determine presidential primaries; but there will be no shortage of remembrances of a bitterly disappointing time for Republicans.
Third, he is going to have to win over Christian conservatives in Iowa, South Carolina and elsewhere. Sure, he talks a good game on religion these days, but let's face it: He has a huge personal issue that he's going to have to explain, again and again: "Gingrich, who frequently campaigned on family values issues, divorced his second wife, Marianne, in 2000 after his attorneys acknowledged Gingrich's relationship with his current wife, Callista Bisek, a former congressional aide more than 20 years younger than he is. His first marriage, to his former high school geometry teacher, Jackie Battley, ended in divorce in 1981. Although Gingrich has said he doesn't remember it, Battley has said Gingrich discussed divorce terms with her while she was recuperating in the hospital from cancer surgery."
I've never thought he was electable as president simply because he is so personally unappealing a character and so obviously an ideologue who thinks he is far smarter than he obviously is.