Economically, Van Buren County has long been driven by a mix of farming, manufacturing, tourism, and collection of small businesses and restaurants. Wineries in particular are a specialty in the county seat of Paw Paw (population 3,000). Located on the coast of Lake Michigan, the county boasts a mix of Chicago tourists and full-time retirees, especially in the town of South Haven. A bedroom community for some, residents may drive into nearby Kalamazoo for employment. With a median household income of $52,351, the county is slightly less well off than the nation’s median of $60,293. It’s Van Buren’s small businesses that have been hit hardest in the four years since the last election, with the COVID-19 pandemic bringing on hardship that is troubling some owners as they fill out their ballot.

“My husband and I have not been able to make a decision,” said Sarah Cox, a restaurant owner in the county. “Because if we went based on our morals, it would go one way. And if we base our opinion on our business, it goes in a completely different way. I think that’s excruciatingly common for people around here.”

But according to County Clerk Suzie Roehm who’s worked in the clerk’s office for the past 25 years, most people in the county have no clue about their reputation for picking winners. “I don’t think most people are aware of it,” Roehm said. “If you are involved at all in the political arena, you probably are aware of it. But I don’t know that the general public would actually know that––I’ve never had a lot of people bring that up to me.”

Just ask 75-year-old Trump supporter John Hunt, who hadn’t heard of the trend and didn’t think he should have either.

“Now, how the hell would I know that?” Hunt said. “I’ve voted Republican all my life except for John Kennedy.”

Democrat Jenna Radabaugh, a 22-year-old daytime manager at a local tap house who cast her Biden ballot last week, was equally taken aback by Van Buren County’s history as a bellwether, as were Paw Paw restaurant owners Eric Cook, 36, and Cox, 44, who both gave similar versions of the “No way! Are you serious?” reaction.

“No, I’ve never heard of that,” Radabaugh said. “But that is kind of shocking to me. Because ever since I’ve been here, it has felt pretty Republican.”

While the county obviously voted blue in the 2008 and 2012 presidential elections, helping keep its streak intact, Radabaugh’s assumption would appear mostly correct, especially when it comes to local politics.

Van Buren County has backed the Republican candidate as the U.S. representative for Michigan’s sixth congressional district for 14 elections in a row and has shown similar support for Republican gubernatorial candidates, voting red in four of the past five such elections. Further, the county hasn’t voted for a Democrat to hold office as a state senator, representative, or secretary of state in the past 20 years.

Outside of Obama’s two terms, the county’s few instances of leaning left have largely come when supporting Democratic candidates for the U.S. Senate, which they’ve done in five out of the past seven elections. While the county’s broad preference for conservative politicians despite brief instances of support for liberals may be confounding to most, Paul Clements, a political science professor at nearby Western Michigan University who lost two of the aforementioned 14 races for representative of Michigan’s sixth congressional district, has some thoughts on the matter.

“I think of Van Buren County like small-town America with a few edges that take you in different directions,” Clements said. “I think there are a lot of liberals there, but they’re sort of moderate liberals. And there are a lot of conservatives there, but they’re sort of moderate conservatives.”

While Van Buren County certainly isn’t a perfect representative cross-section of America––on average, it is whiter, older, and less wealthy than the country as a whole––Clements does support the notion that Van Buren County may just simply be more moderate, especially in comparison to its bordering counties.

Whereas Kalamazoo County, a metropolitan area that sits directly to the east of Van Buren, is more progressive in nature, and Allegan County, immediately north of Van Buren, is traditionally conservative, Clements says Van Buren County is “right in the middle”––geographically and politically.

To Clements, the more moderate nature of Van Buren County’s electorate explains in part why the county has fluidly switched between right and left and back again in presidential elections. More moderate voters naturally may be swayed more by individual candidates; for example, whereas Obama’s charisma, message of hope, and potential to be the nation’s first African-American President may have swayed moderate voters to turn out to vote, Hillary Clinton’s candidacy did not, according to Clements.

Explaining Van Buren’s preference for conservative politics outside of presidential elections, Clements points to the institutional history of the Republican Party in the county. Having been around far longer than its Democratic counterpart, the Republican Party has held all of the county’s commission seats for as long as Clements can remember.

“The Democratic Party has only really begun to field candidates for a number of the positions within the county,” Clements said. “So part of the reason you know that the Republicans win down the ballot is that they’ve just been there [longer].”

According to Paw Paw locals, outward support for Trump has been more prominent than for Biden: A Trump Train Cruise of more than 200 cars came through the town over a month ago, and another one blasted through East Michigan Avenue––Paw Paw’s main road that is home to its local restaurants, diners, and movie theatre––on Saturday. Trump campaign posters appeared to outnumber those of Biden, but not by much.

Van Buren County, of course, will have little impact on the final Electoral College tally, and its previous alignment with presidential winners means little in terms of its future accuracy. Most think the vote will end up being close, and some Van Buren County residents think this is the year the trend comes to an end.

“If I had to bet, I think this is the year the streak ends,” said Cook, the owner of 120 Taphouse & Bistro in Paw Paw. “Just gut feeling––I definitely think we buck the trend. I would guess that Biden would be elected nationally, but that Trump probably has a good chance of winning this county.”