I think Sunny should have won. She was the original Diva. Everything Sable was in the WWF was what Sunny was supposed to have but she threw it all away before it happened. Playboy wanted Sunny because she was the most downloaded woman on the internet, she beat out Pamela Anderson. But Sunny turned down Playboy for whatever reason, but then turned around and posed nude for some shitty website for peanuts. She could have been the top selling Playboy cover girl of all time, but instead that went to Sable. I'm sure Vince would have brought back the Woman's Championship for Sunny because she was the hottest Diva and most popular Diva in WWF history. But she left and the belt and playboy went to Sable.
I don't know why Torrie Wilson never won, she was the top Diva in the company after Vince bought WCW. She was the next Sable in Playboy, and had a great feud with Dawn Marie in a step-mother / step-daughter match. That should have been for the title. Unfortunately, this was back when Raw and Smackdown were divided and she was on Smackdown and the Woman's Championship was on Raw around Trish Stratus' waist. Not long after Torrie was gone they brought in the Diva's Championship so both shows could have a woman's champion. But it was too late for Torrie.
Stacy should have been a huge star and champion but they never really pushed her as a wrestler. I assume it was her choice not to wrestle, but when she did the fans loved it. Gorgeous George would have been the champion if WCW had a woman's champion, or if they let her come to the WWF. She should have after Vince bought WCW but by then she was gone.
Technically Maria won a woman's championship but its not in TNA or WWE so I didn't count it. So she shouldn't really be on this list.