Playing the Woman Card
Negan is not someone to discriminate against anyone. Like him or hate him, he has respect for women. He hates people who mistreat women, won’t force any of his wives to do anything against their will and he keeps women in some of the highest roles available among the Saviors.
Regina is a tough lady and she means business. If she had to side with any of the other lieutenants, it’s clear that she falls in line with Simon and is willing to do anything to save her own life. She’s definitely a badass, but she’s her own badass. In fact, the order of operation is her life above all others, then the Saviors and then the workers at the Sanctuary. Negan, of course, is at the top of that list. Unless he isn’t there.
What’s interesting about Regina is that Negan treats her like one of the guys. He treats all of his people the same way. So rather than it being a big deal that Regina is a woman in the inner circles of the Saviors, it’s a bigger deal for everyone else to see her there. It shows that Negan isn’t a misogynist and that anyone can have that spot if it is earned.
With that in mind, Negan is an equal opportunity leader. If he suspects that Regina might be too close to Simon’s way of doing business, he’s not going to have problems punishing or killing a woman just because she’s a woman. That’s a very important distinction.