The decline of heraldry is quite noticable on my city's coat of arms as well, the progression is like this:
1. original simple: https://sk.wikipedia.org/wiki/S%C3%BAbor:Coat_of_Arms_of_Sta...
2. newer: https://sk.wikipedia.org/wiki/S%C3%BAbor:Coat_of_Arms_of_Ko%...
3. newest: https://sk.wikipedia.org/wiki/S%C3%BAbor:Great_Coat_of_Arms_...
But Milwaukee has very little to do with global combat or diplomacy. They don't issue passports or interact with all the other cities in the country. Their flag doesn't need to stand out from all the others at a distance or to non English speakers; it is functionally a sentimental, commemorative quilt to hang at city hall. It wasn't hurting anybody.
> “I wish we would take a breath and not just get rid of everything. because good or bad, it is our history.” [0]
[0]: https://www.kltv.com/2020/06/19/webxtra-family-woman-who-por...
tfa appears to admit that people are actually _using_ the new Milwaukee flag. This seems like a pretty strong argument that the new flag actually is better than the old flag? It is kinda cool to have a very distinctive local flag, but if the practical upshot of that is that the flag isn't actually used anywhere except a single flagpole in front of city hall (if that), seems like the vexillology people kind of have a point?