Longest negative popular vote bellwether US county streak?

Question

I was thinking about negative bellwethers, which are things that generally pick the losing candidate. A positive popular vote bellwether could be New Mexico dating back to 1964. This means it always picked the candidate winning the national popular vote for president. I was thinking about the opposite: a negative bellwether county. This is the best example of a negative popular vote bellwether I could find: Vermont gubernatorial elections relative to presidential elections in presidential years and House relative to the election 2 years after (midterm):

Year, VT voting for winning party nationally
2006, No
2008, No
2010, No
2012, Yes
2014, No
2016, No
2018, No
2020, No

At the county level (for president), what is the longest negative bellwether streak? Such a county, from 2000 on, would vote Bush, Kerry, McCain, Romney, and Trump. What county has done this?

Answer 1

For the period you describe in the question, we can use the MEDSL dataset which covers recent county-level presidential election returns since 2000. There are three counties which have consistently voted for the candidate which lost the popular vote, all three within the same state - Kentucky. Bath, Carter, & Magoffin County have all voted for Bush, Kerry, McCain, Romney, & Trump (2016 & 2020). However, all three counties also voted for Clinton in 1996, meaning that all three counties have voted for the candidate which lost the popular vote six times in a row.

More broadly, using the University of Michigan dataset found here, in conjunction with Dave Leip's Atlas of U.S. Elections, the county which picked the longest streak of losing candidates I could identify was Holmes County, Mississippi. The county voted for the losing candidate in each election from 1948 to 1972 inclusive; seven consecutive presidential elections. The county voted for Dixiecrat candidates in '48, '56, & '60, Stevenson over Eisenhower in '52, Goldwater over LBJ in '64, Humphrey over Nixon in '68, and McGovern over Nixon in '72. The streak was broken in '76 when the county voted for Jimmy Carter.