Wisconsin: Largest Trump '16 City:
#7: Waukesha.... Tilt / Likely Trump 2020...
So--- I thought it might be a good idea to review the Top Ten largest Cities in Wisconsin, especially in light of recent events...
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Will Green Bay or Appleton flip in 2020 from HRC > Trump?
What about recent unrest in Kenosha in a heavily HRC '16 City?
Is there any reason to suspect that Waukesha might flip in 2020 for Biden?
Could Oshkosh flip before Green Bay or Appleton?
Since we're talking about the city proper areas, rather than their corresponding counties, these are interesting questions.
On the first point (GB and/or Appleton), I think the answer in a solid no on that flip, especially given the current national environment and the increasing trends towards the Democrats in urban and suburban areas. Joe Biden should see improvement on HRC's margins in both GB and Appleton.
On the second point (Kenosha), the recent unrest should not heavily influence Kenosha. It should still be a strong D bastion, especially with this environment. Polling indicates that Trump's response on the civil unrest was viewed more negatively, in general, because he did not do enough or he stoked the flames more than anything else. Some of his actions, particularly his comment on Kenosha not existing if it weren't for him or that photo shoot at a store against the present owner's consent, did do Trump any favors for Kenosha locals either.
On the third point (Waukesha), are we talking about the county or the city? If it's the city, there's a strong chance it will. In fact, if the environment remains unchanged or if it worsens for Trump, I believe one of the WOW counties may finally jump ship from Republicans à la Orange County (or at least come close). In that scenario, cities like Waukesha would be one of the big reasons why that happens (it was D-5 for Baldwin in 2018).
On the last point (city of Oshkosh), it could flip R, but not in this environment.