An analogy, for your consideration: Clackamas County is to Oregon as Florida is to the rest of the United States. 

The county is currently in the final throes of a ballot-counting disaster that is ripe for dissection by conspiracy theorists on all sides (Vote by mail is corrupt and needs to be replaced! No, the county clerk is a Trump acolyte who is actively trying to undermine faith in the system! Commence panic!), recalling the dimpled ballots, hanging chads, and drawn-out vote count and recount of Florida, 2000. 

But the ballot kerfuffle—in which longtime County Clerk Sherry Hall knew before Election Day that there had been a Florida Man–worthy printing error rendering two-thirds of the county’s ballots unreadable by machine and forcing them to be duplicated by hand, a time-consuming process that overlapped with a Congressional race of national significance—is only the latest in a long line of eyebrow raises from the county, which spans from Portland’s wealthiest, leafy southern suburbs to fast-growing exurbs to the eastern slopes of Mount Hood.  

There for the Right Reasons? 

Though east of the Cascades is generally considered the state’s firmest Republican stronghold, Clackamas County has a history as a headquarters for some of the state’s most notorious right-wing operators. Anti-tax activist Bill Sizemore, whose glory days in the 1990s fundamentally changed property taxation in the state, had a base there before moving east of the Cascades. He eventually (and ironically) pled guilty to tax evasion and served a brief stint in jail; he has run numerous times for governor, including in 2022, to ever-dwindling returns.  

The Oregon Citizens Alliance, which was behind a 1992 anti-gay ballot measure was also based in the county; Measure 9 failed, though 12 years later similar groups would sway a majority of voters to ban same-sex marriage in Oregon (a rule overturned by the state Supreme Court in 2014). 

Today, registered Democrats outnumber registered Republicans in Clackamas County by about 20,000 voters, but notoriously fickle and hard-to-pin-down nonaffiliated voters are within about 8,000 voters of overtaking Democrats. 

The county’s decidedly non-Portland rightward bent was on full display during the pandemic when elected County Commissioner Mark Shull decided, in quick succession, to post a Facebook meme that likened COVID-19 restrictions to the Holocaust, publicly suggested that COVID vaccine passport rules were akin to Jim Crow’s doctrine of legal segregation in the American South, and posted Islamophobic and anti-transgender slurs on social media accounts. Shull, who still serves on the board, blamed the resultant outcry on “cancel culture.” A recall campaign to remove him from his post is moving along at a glacial pace; it’s unclear whether organizers will muster enough signatures to force a vote on his removal before his term is up in 2024. 

Shull’s actions were condemned by the other four members of the Clackamas County Commission, but one of his fellow commissioners, former State Rep. Tootie Smith, made waves of her own when she told Fox News host Tucker Carlson that she planned to host a big Thanksgiving gathering for family and friends in November 2020, when Gov. Kate Brown had ordered a limit on social gatherings, to just six people from two households, to slow the spread of COVID-19. (Previously, Smith was well-known for raffling off a 9 mm Glock pistol at a political fundraiser; she has described herself as a “Second Amendment rights advocate” and noted that “guns are really big in Clackamas County.”) 

The Maybe City 

Curiouser and curiouser—a good motto for the now-you-see-it-now-you-don't city (or is it?) of Damascus in Clackamas County. The area used to be firmly unincorporated, until regional government Metro changed the urban growth boundary and a handful of residents thought they should incorporate as a city, to gain more control over their own destiny. As it happens, not everyone agreed, setting in motion a tug-of-war over whether the city had the legal right to exist or not.  

At last check, quintessential exurb Happy Valley had annexed a big chunk of the city formerly known as Damascus (though a small band of believers continued to hold meetings in the former city hall location, despite its being sold off to a liquor store); meanwhile, the Oregon Supreme Court weighed in with the (we think?) final word in 2020, ruling in favor of disincorporation. 

Jeepers, Creepers 

Set the wayback machine to the following clutch of headlines: Politics of Place: Clackamas Voters Get Rebellious, Shift to the Right, (from the Oregonian, in October 2012), The King of Clackistan, (from Willamette Week, also October 2012) and Checkpoint, Clackamas (from an ahead-of-the-game Portland Mercury, May 2012). 

A decade ago, Clackamas County residents were up in arms about the notion of “Portland creep,” touched off by TriMet's proposal to extend MAX service from downtown Portland to Milwaukie, a logical extension of Clackamas taxpayers’ widespread former reluctance to help pay for improvements to the decaying Sellwood Bridge, a key link for many of its commuters. (Eventually, they’d lose both fights—the Orange MAX line to Milwaukie/Oak Grove opened in 2015; a refurbished Sellwood Bridge came a year or so later. There’s still no streetcar extension to Lake Oswego, though, another perennial Clackamas County bogeyman).  

Anti-Portland billboards sprouted up around the county and deep-pocketed PACs spent big on electing well-right-of-center officials; one of those was Smith, who is the current chair of the Clackamas County Commission.  

The latest target of commuter fury in the county? A proposal to put a toll or congestion pricing on I-205, another key link between Clackamas County and the rest of the metro area. Of course, if the tolls go through, that Florida likeness could grow even stronger: the Sunshine State leads the nation in miles of toll roads.