Gingrich may have spent his entire life in Washington and be so much of an insider that, as Jon Stewart says, “when Washington gets its prostate checked, it tickles [Newt],” but he is deemed the rebellious outsider challenging “the Establishment” — because, again, “the Establishment” is anyone who opposes Newt.
Best response I can think to this is: Is that why they kicked him out? What, the 1998 elections didn’t turn out great. Big deal. So, the Republicans kicked out the “insider” Newt and replaced Newt with ... that unmemorable person.
Newt may be imperfect, he may have sat with Pelosi, endorsed Scozzafava, and been pro-global warming, but if he keeps saying the right things, I’m happy to support/endorse him.
It's more like he sat with and endorsed imperfect people. So has Mitt and so has Santorum.
It has nothing to do with being an insider or outsider - the establishment doesn't want anyone rocking their boat. Palin was not an insider but they got seasick just knowing what she is capable of. Same with Newt.