Behaviour of Trump-trending counties that stayed blue in 2016
There were a number of counties that had last voted Republican no more recently than 1988, where Trump came within 6% of winning in 2016. Because of the margin, one could have expected him to have flipped these counties in 2020, if he were winning reelection. (On election night, Jason Miller gave, as reason for optimism on the Trump side, that Trump appeared to be increasing his margin in counties that were at least 75% in in Michigan by 6-7%; 'increasing' a negative 'margin' of any less than -6% by that much would mean flipping the county.) (Bold indicates Trump increased his vote share in the county in 2020; the colour is of the party that carried the county in 2020. Asterisk indicates that Trump's 2020 vote share was the highest of any Republican's this century.)
Russell, AL (-1.6%)
Lake, CA (+2.8%)*
Gilpin, CO (-0.003%)
Tolland, CT (-1.0%)
Peoria, IL (+0.5%)
St Clair, IL (+0.2%)*
Jackson, IL (+4.0%)*
Scott, IA (+1.8%)
Tensas, LA (+0.5%)
York, ME (-1.8%)
Muskegon, MI (+2.9%)*
Marquette, MI (-0.7%)
Lake, MN (+2.1%)*
Carlton, MN (+3.3%)*
Big Horn, MT (+2.4%)
Merrimack, NH (-0.9%)
Clinton, NY (+1.5%)*
Pasquotank, NC (+2.1%)*
Mahoning, OH (+4.1%)*
Lorain, OH (+2.9%)*
Clatsop, OR (+1.3%)
Lackawanna, PA (-1.1%)
Lehigh, PA (+0.2%)
Bucks, PA (-0.5%)
Dillon, SC (+2.0%)*
Clarendon, SC (+2.0%)*
Franklin, VT (+2.7%)
Rutland, VT (+1.1%)
Portage, WI (+2.7%)*
Green, WI (+1.7%)*
There are a further set of counties which may or may not have been particularly close, but where Trump got the highest vote share of any Republican this century in 2016. If they were not close, one might not have expected him to flip them, but it is still of interest whether Trump continued to improve in these counties in 2020. (By definition, any county that is bolded is also one where Trump got the highest Republican vote share this century.)
St Francis, AR (+2.6%)
Lee, AR (+4.6%)
Desha, AR (+1.0%)
Chicot, AR (+1.6%)
Gilpin, CO (-0.003%)
Middlesex, CT (-2.9%)
New London, CT (-5.0%)
Tolland, CT (-1.0%)
Taliaferro, GA (-0.1%)
Hancock, GA (+4.2%)
Clay, GA (-0.1%)
Jackson, IL (+4.0%)
St Helena, LA (+2.2%)
Iberville, LA (+1.6%)
St James, LA (+2.1%)
Bristol, MA (+1.1%)
Hampden, MA (+1.8%)
Genesee, MI (+1.9%)
Muskegon, MI (+2.9%)
Lake, MN (+2.1%)
Carlton, MN (+3.3%)
St Louis County, MN (+1.3%)
Marshall, MS (+3.4%)
Deer Lodge, MT (+2.8%)
Erie, NY (-2.9%)
Northampton, NC (+3.1%)
Scotland, NC (+5.7%)
Anson, NC (+4.8%)
Mahoning, OH (+4.1%)
Lorain, OH (+2.9%)
Summit, OH (+1.4%)
Athens, OH (+3.4%)
Lackawanna, PA (-1.1%)
Providence, RI (+1.0%)
Dillon, SC (+2.0%)
Marlboro, SC (+3.0%)
Clarendon, SC (+2.0%)
Hampton, SC (+2.4%)
Jasper, SC (+3.8%)
Buffalo, SD (-1.6%)
Haywood, TN (+0.9%)
Duval, TX (+16.8%)
Douglas, WI (+1.4%)
Bayfield, WI (-0.5%)
Ashland, WI (+2.8%)
Menominee, WI (-2.9%)
Portage, WI (+2.7%)
Rock, WI (+2.1%)
A final category of county that one might have expected Trump to have been flipping most of, if he had been winning re-election, are a series of counties that Bush carried at least once and that Hillary Clinton carried by less than 1% and by fewer than 1,000 raw votes. These are counties that are not necessarily trending from Republican to Democratic, but could instead be fitfully trending from purple to Republican. (However, I am excluding counties that otherwise fit this description but that voted for Bob Dole in 1996 [Olmsted, MN, Monroe, PA, Gallatin, MT, Lancaster, NE]--two of which were also Romney-HRC counties--because that voting pattern does indicate a long-term trend from Republican to Democratic. Every county that voted for Dole and for Hillary Clinton also voted for Biden in 2020; and Trump's vote share went down in all the above-named counties in particular save Gallatin, where it increased by 0.3% [but which he nevertheless lost by 7.5%].)
Washington, GA (2016 margin: 0.6%/51 votes) (+0.3%)
Winnebago, IL (2016 margin: 0.1%/89 votes) (+1.4%)
St Joseph, IN (2016 margin: 0.2%/231 votes) (-0.4%)
Waldo, ME (2016 margin: 0.3%/62 votes) (+0.3%)
Pike, MS (2016 margin: 0.2%/34 votes) (-0.1%)
Dutchess, NY (2016 margin: 0.3%/464 votes) (-2.9%)
Orleans, VT (2016 margin: 0.2%/26 votes) (+3.4%)
Clark, WA (2016 margin: 0.2%/316 votes) (+1.5%)
Trump didn't flip any of these. One interesting near-flip that had also voted for Bush at least once was Stanislaus, CA, which Trump lost in 2020 by 0.8%--a smaller margin than he lost any of the above counties by save Washington, GA. Stanislaus had been close in 2016, albeit not as close as any of the above in either percent or raw vote terms (1.8%/3,153 votes). Trump added 3.2% to his vote share in Stanislaus in 2020--the first time the Republican vote share in the county had gone up since 2004. Stanislaus has in common with another county that actually did flip from Hillary Clinton to Trump--Val Verde, TX--that it was a bellwether county whose winning streak was broken in 2016, and whose winning streak had begun in 1972 (i.e. after voting for Hubert Humphrey).
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