How do you think Negan would have responded to the Season 8 hostage situation had Rick not ran him off the road to be captured by Anne? Would he actually bend? Would he likewise sacrifice them, albeit apologetically? Thoughts?
I don't think so. Negan's mantra has always been "people are a resource" and he shut Simon down when he expressed a desire to kill them all (when zombified Dean was delivered). I think it was because of Simon that Negan had to change his plan since Simon took it upon himself to try to kill everyone at Hilltop (while Negan was Anne's hostage). After all, Negan 's last words to Simon were about how Negan now has to kill everyone thanks to Simon's recklessness. I think Negan wanted to free the hostages while killing a few of his enemy as possible because "people are a resource ".
I think he failed to take into account exactly how stubborn the Militia was. Simon was right when he argued that this whole "kill one, spare the rest" strategy was no longer working. If Simon were less hot headed and Negan was less egotistical, then I think they could have worked together much more effectively and actually defeated the militia, maybe even successfully rescuing their men in the process. However, it seems like Negan eventually decided Simon was right after all in "Wrath" when he attempted to kill them all with the firing line.