"Don't piss the lady off"

Chryson says Stein’s big mistake was taking Palin for granted.

“He thought that Sarah was going to be their rubber stamp. And he wound up getting snake-bit,” he says.

Fifteen years later, Stein still seems shell-shocked by the intensity of the ensuing mayoral campaign. In Alaska, city races are officially nonpartisan, but Palin came after him on big ideological issues like abortion and gun rights.

“And there was such enthusiasm from the — I’m laughing now, [but] I’m crying on the inside — there was such enthusiasm in the community for this, you know — ‘Yes, we’re talking philosophy here now.’ And here I am, down there, going, ‘But I can fill potholes,’ and, ‘I understand how sewage treatment plants work.’ But that really wasn’t the point, anymore,” Stein says.

She beat him — and then, in a rematch three years later, she clobbered him, 3-to-1. Chryson sees a clear lesson in Stein’s experience.

“The one thing I can say about that is: Don’t piss the lady off,” he says.