I don't understand...(Max Payne 2 and I guess 3 spoilers)

#1Zin_LGPosted 1/11/2013 8:21:28 AM(edited)
I don't understand why killing Winterson was Max's biggest regret. He knows she was involved with Vlad and his plan and also that she was going to kill him and Mona.

I get that Max and Winterson were two sides of the same coin, two seemingly good cops that became romantically involved with criminals and killers. I just don't understand why Max feels that much regret over Winterson when Mona had his back to the end. Also why he is building her up to be a better cop than she was especially since she went out with the intent to commit murder.
Backlog progress: PS3- 26/43, 360 - 4/8, PSP- 14/48, PC ??/??
Recent completes - Heavy Rain :DC, Bastion, L.A. Noire, Assassin's Creed 2, NIER, Dante's Inferno