I’m not saying he wasn’t progressive for his time in the context of those stories, but progressive for his time still meant the utter suppression of women within the culture.
Women weren’t allowed to have opinions, conduct trade, or own property, because they were property themselves. eta: and Jesus didn’t explicitly say women should have those rights.
If you believe the bible is the infallible word of god, it shouldn’t be controversial that women are like livestock.
Now, you can rationalise progressive values by saying if Jesus was alive today, he wouldn’t have gone along with all that, but that’s just not what the bible actually says.
Considering evolutionary time scales, this trait may have been a response to something large and dangerous that’s extinct now.