I keep expecting America’s trendsetters to get over Portland, Oregon, but the odes to the City of Roses just keep on coming. The Portland tourism board could compile an impressive anthology of the New York Times’s recent coverage of the city, most of which couldn’t be more fawning if it were bylined by Bambi.

In fairness to the Times’s travel writers, once you get past the fact it rains nearly six months out of the year, it’s hard to blame them for wanting to write about the city. At the base of soaring Mt. Hood and the gateway to the Columbia River Gorge, Portland might have the most beautiful natural setting of any major city in America. Its isolation has incubated a distinctive culture, and by any measure its art and culinary scenes are far more exciting than any city this size (nearly 600,000 people) should rightfully produce.

Still, that doesn’t adequately explain why Portland looms so large in the imagination of the Paper of Record. Things reached the point in 2009 that a columnist for the Oregonian actually wrote a Dear John letter to the Gray Lady, announcing, “Sorry, NYT, we’re just not that into you”:

Look, we know you have strong feelings for us. We can tell​—​like the rest of the English-speaking world​—​by your incessant need to write about us.

Two weeks ago, you made “Frugal Portland” the Sunday Travel centerpiece. In early April, you devoted another travel cover to touring our fair city by bike. You’ve also written recently about our conflicted attitudes toward gentrification, our quest for big-league soccer and our openly gay mayor, not to mention our great food, rainy weather and communal caffeine addiction.

It’s getting embarrassing.

Speaking of embarrassing, during a recent visit to the city I got a firsthand lesson on what a fishbowl Portland has become. I was having a meal at a small-but-shockingly-good French bistro a block from my hotel downtown and struck up a conversation with the man next to me at the bar. He was an engineer at a local foundry, and about as close to a regular guy as you’re likely to find in a city noted for its bohemianism, so I was interested in his thoughts. I mentioned that I was a journalist from the East Coast, and he immediately announced he could not be quoted by name and turned the tables on me, demanding I explain “why the [expletive] New York Times likes us so much.”

Alas, the Times’s pining for Portland may be unrequited, but the paper keeps penning more mash notes. I would later find out that the Little Bird Bistro, scene of this aborted conversation, had been prominently featured in a New York Times travel column last summer and got a full-blown review in January. The Oregonian’s website even had a blog post grumbling about how the Times was constantly letting the cat out of the bag regarding the locals’ favorite establishments. Thanks to the publicity, it now would be harder to get a table at Little Bird. Oh, and in case you’re looking for that first Times write-up of the restaurant, I should note it was in the “36 Hours in Portland, Ore.” feature in August 2011​—​not to be confused with the “36 Hours in Portland, Ore.” piece the paper ran in 2007. Last year’s travelogue pronounced Portland “the capital of West Coast urban cool,” while the 2007 piece said it “overflows with urban pleasures like chic restaurants, funky nightclubs and spritely neighborhoods crackling with youthful energy, but nobody’s boasting”—except, that is, the New York Times.

So it was with some relief that audiences welcomed the sketch comedy show Portlandia on television last year, with its implicit promise that the city and the hype surrounding it were finally in for some richly deserved skewering. Starring Saturday Night Live journeyman Fred Armisen and Carrie Brownstein​—​a former member of feminist “riot grrrl” band Sleater-Kinney and a Portland celebrity​—​the show has mostly made good on that promise, wringing humor out of the city’s intersection of hipster culture and progressive politics.

Portlandia instantly struck a chord as a Garrison Keillor-type takeoff on the edgy urban set. Instead of idyllic Lake Wobegon, where “all the women are strong, all the men are good looking, and all the children are above average,” Portlandia is where “the tattoo ink never runs dry” and “all the hot women wear glasses.” The show is now in its second season and has even spawned a live comedy tour that’s bringing Portland to a venue near you.

But while Portlandia is more acerbic than Prairie Home Companion, it too can come off as a twee, chiaroscuro character study that spends as much time burnishing the city’s reputation for “West Coast urban cool” as it does mocking it. And there’s nothing necessarily wrong with that. I’m just afraid that the real-life absurdities of Portland merit a more cutting critique.

Case in point: One of the most commented-on sketches from the show is a scene from the first episode in which Armisen and Brownstein are sitting in a restaurant. After asking their waitress a series of absurd questions about whether the chicken they are about to eat is local​—​“the chicken is a heritage breed, woodland raised chicken that’s been fed a diet of sheep’s milk, soy, and hazelnuts. .  .  . His name was Colin, here are his papers”​—​the couple ends up leaving the restaurant and driving to the farm to see the environment where the chicken was raised in order to assuage their guilt about eating it.

As a comment on urban America’s foodie culture, the sketch is funny and incisive. But it doesn’t begin to show how insufferable Portland actually is in this regard. Portland’s restaurants are incredibly good, provided you don’t gag on their politics and pretension. It’s common for restaurants to brag about keeping “food miles” to a minimum​—​a rough calculation on the menu informing you how far all the ingredients have traveled to your plate, as if this were a rational measure of the restaurant’s environmental impact. One Portland ice cream parlor I visited recently was inviting patrons to swing by on Saturday afternoon for a meet and greet with the local producer of its “artisanal finishing salts.”

And in 2010, the Oregonian actually ran a story with the headline “Portland pig cook-off followed by brawl over the provenance of pork.” During a local culinary competition a fistfight broke out because one of the chefs​—​the horror!​—​wasn’t using locally sourced pork. The mêlée ended with one of the chefs and the organizer in rough-looking mug shots and the latter in the hospital with a fractured tibia. When it comes to the city’s food obsession, the truth far outstrips Portlandia.

Given the lack of critical attention to the city, I guess it falls to me to state the obvious: Portland is quietly closing in on San Francisco as the American city that has most conspicuously taken leave of its senses.

While I don’t blame Portlanders for being suspicious of interlopers who write about their city, I should mention that I am an Oregonian​—​albeit one who hasn’t lived in my home state for 13 years. But my mother and her three siblings were raised in Portland, I still have relatives in the area, and I lived in the city for a short time after college.

So I may be 3,000 miles away as I write this, but I’m not a disinterested observer. Perhaps some time and distance are needed before rendering an impartial judgment on what has become of a city that you truly know and love. Unlike the New York Times, I write not to praise the place but to note the litany of things that plainly have gone wrong. Also to alert anyone else who’s listening: Right now, America’s civil and social engineers are beavering away trying to turn your city or town into the next Portlandia.

"It sometimes seems as if the whole country is looking to Portland as a role model for 21st-century urban development,” Governing wrote of the city. Clearly the magazine knew nothing about the political history that has turned Portland into a caricature of itself. God help us if this is America’s civic ideal.

The major justification for our increasing urbanization​—​and 243 million Americans now live in urban environs​—​is that “urban density provides the clearest path from poverty to prosperity,” writes Harvard economist Edward Glaeser in Triumph of the City: How Our Greatest Invention Makes Us Richer, Smarter, Greener, Healthier, and Happier. Great cities are remarkably good at generating wealth, and here Glaeser provides a useful comparison: Workers in the five zip codes that occupy Manhattan between 41st Street and 59th have a larger payroll than the entire state of Oregon.

Of course, if Oregon doesn’t have a bigger payroll, that might be because over half the state’s residents live in or near a metro area that has spent nearly 40 years justifying political corruption and heavy-handed economic regulations as forward-looking environmental policy.

Things began to unravel in 1973, when the Oregon legislature required cities in the state to set development boundaries with the goal of preserving farmland from “leapfrog development”​—​that is, new subdivisions not adjacent to established developments. Portland became the first major city with an “urban growth boundary.”

This fact opened up a world of possibilities that are still being inflicted upon us. “Urban planners have long believed in a land-use-transportation connection that would allow them to manipulate one through the other,” writes Cato Institute senior fellow Randal O’Toole in a damning policy paper on the failure of Portland’s growth policies. “So Portland plans land uses to try to reduce the amount of driving people do while it plans transportation to try to slow the conversion of rural land to urban purposes.”

The same year Portland began implementing its urban growth boundary, Neil Goldschmidt became mayor. Goldschmidt quickly recognized that the land-use-transportation connection could be exploited to political ends, and this insight would make him the state’s largest powerbroker for decades to come.

In 1974, Goldschmidt canceled a major interstate freeway project before it broke ground. Aside from the usual gripes about a freeway reducing nearby property values, Congress had just passed a law allowing federal highway funds to be used on capital improvement for public transportation. More public transportation looked like a good way of helping Portland stay within its urban growth boundary.

The problem was that the feds had allocated so much for the highway project that the city couldn’t possibly absorb it all in buses. Goldschmidt had to find an irrationally expensive new mode of public transportation, and thus began liberal America’s love affair with “light rail.” And light rail had another advantage over buses, namely that the laying of tracks and the placement of stations allowed Goldschmidt even more power to manipulate land use, making him a kingmaker among developers. Naturally, Goldschmidt’s pioneering of a public works project distinguished by its exorbitant cost earned him a job as Jimmy Carter’s secretary of transportation.

Vaunted though it might be, Portland’s light rail system hasn’t been the success its planners hoped. It’s called “light” rail not because the trains are less heavy, but because it’s more lightly used by the public than, say, New York’s subway or Washington, D.C.’s Metro. Over the course of the 1980s, the city’s first light rail line was finally completed, and the percentage of Portlanders using public transportation declined.

By 1987 Goldschmidt had been elected governor. During his term, the state began requiring urban areas to adopt plans to reduce per capita driving by 10 percent in 20 years and 20 percent in 30 years.

This necessitated new restrictions on development. “To reach those goals, the rule specified that planners must increase residential densities, promote mixed-use developments, mandate pedestrian-friendly design (meaning, among other things, that retail shops should front on sidewalks and not be separated from streets by large parking lots), and various related policies,” writes O’Toole.

As for Goldschmidt, he stunned political observers by leaving the governor’s office in 1990 after one term. But he found private employment much more lucrative than public service. He founded the consulting firm of Goldschmidt Imeson Carter, and you’d have to draw up an impressive flowchart to keep track of the interconnected corporate and civic interests that quickly put him on retainer. It seems Goldschmidt’s services were heavily in demand​—​primarily from people who wanted him to help navigate the draconian development restrictions that he himself had put in place.

In 1995, Portland’s city council was so enamored of the town’s status on the bleeding edge of urban planning that it adopted the slogan “The City That Works,” previously used by Mayor Richard J. Daley’s Chicago. And comparison to Chicago’s sleazy machine politics became apt in 2004 when a scandal erupted in the Portland papers over what was dubbed the “light rail mafia.” Contain your surprise, but it seems Oregon’s integrated land use and transportation planning system was being manipulated to award Goldschmidt’s consulting clients hundreds of millions in state and city contracts relating to light rail expansion and the accompanying high-density developments.

This morass of rules that has retarded the city’s economy and facilitated political boondoggles seems like one hell of a price to pay to justify the existence of an arbitrary boundary line and a public transportation system that, according to O’Toole, has reduced vehicle use in Portland about 1 percent. Nonetheless, Portland remains firmly in the grip of mass-transit mania. The city proposed a budget in January that would eliminate “major road paving” for the next five years, apparently under the theory that the only way finally to get cars off the road is to let the potholes swallow them whole.

But America’s enlightened planners and progressive politicians must be aware of something I’m not​—​Portland’s decision to tie land use rules and transportation plans is now popularly known as “smart growth.”

True to form, the Obama administration is investing in the hope that other cities will copy Portland. In 2010, Obama’s Housing and Urban Development secretary, Shaun Donovan, traveled there to announce a new Office of Sustainable Housing and Communities, doling out $140 million in regional grants to “integrate economic development, land use, transportation, and water infrastructure investments, and to integrate workforce development with transit-oriented development.” Said Donovan, “We at HUD are big admirers of what you’re doing here.”

The rush to praise Portland’s smart-growth policies has been strangely unimpeded by their results. Oregon’s urban growth boundary is defended from criticism as if it were the Maginot Line of American environmentalism, but, tellingly, its supporters don’t even pretend it makes for prudent economic policy. Rather, it’s just one of those things that make Portland’s culture so darn special. A 2010 article in Good magazine​—​a publication of environmentalist bent, chiefly notable for employing Albert Gore III​—​described it this way:

Along with creating dense neighborhoods, encouraging mass-transit use, and irritating free-market zealots, the growth boundary saves farmland close to the city. The resulting proximity between country and town defines life here. Portland is a small-to-medium city with a frequently dismal economy, a single major sports team that hasn’t won a championship in 30 years, and world-class access to premium local produce. Ambitious small restaurants crowd the city, bedazzling visiting food critics from New York; some Portlanders follow the local pinot noir harvest the way people in Greenwich, Connecticut, track hedge funds. None of this could exist without the boundary.

Portland is indeed surrounded by thousands of square miles of prized Willamette Valley farmland, and a glance at a map will tell you that there’s a long way to go before sprawl is a major concern. Of course, you’re a free market zealot if you oppose the growth boundary, even though it might have something to do with Portland’s “frequently dismal” economy, because​—​well, have you tasted the arugula? It’s world-class.

If you want to credit the growth boundary with preserving the state’s farmland, then you should also have to defend the havoc it’s wreaked inside the city. In 2010, consultant Wendell Cox did a quick survey of the urban growth boundary’s effect on property values in Portland. “The land adjacent to, but outside, the urban growth boundary (on which development is prohibited) was assessed at approximately $16,000 per acre,” he concluded. “The land adjacent to, but inside, the urban growth boundary (on which development is permitted) was assessed at approximately $180,000 per acre, approximately 11 times the price of land that is virtually across the street.” Tough luck for Portland’s homebuyers.

And even as Portland’s growth policies are wrecking the supply of affordable housing, they have contributed to a generally hostile business climate that has sent many of the region’s biggest employers packing.

“We are way too anti-business as we are now,” wrote Nike chairman and cofounder Phil Knight in a letter published in the Oregonian in 2010 shortly after Oregon adopted the nation’s second-highest state income tax rates. “The state in past years was headquarters for the First National Bank, US Bank, Pacific Power, Willamette Industries, Georgia-Pacific, Jantzen, White Stag, G.I. Joe’s, Monaco Coach, Meier & Frank, among many others. They are now headquartered elsewhere, are controlled by non-Oregonians, or no longer exist.” (For what it’s worth, Knight was right to gripe about the tax increase​—​the state saw a 28 percent drop in revenue the year after the new rates took effect.)

Most of these companies had been headquartered in Portland. Even Nike​—one of ​the state’s two Fortune 500 companies​—​has been publicly flirting with leaving the Portland metro area and relocating to Idaho.

Middle class livability was once a hallmark of Portland. My own grandparents moved there during the Depression. My grandmother was a public school teacher and my grandfather drove a Greyhound bus for 35 years while they raised four kids in a small house in north Portland. They made a few smart property investments and were able to retire to a farm just outside Portland so my grandfather could realize his childhood dream of raising quarter horses.

But thanks to the one-two punch of artificially high real estate prices and an eroding jobs base, my grandparents’ upwardly mobile, working-class life now seems out of reach for much of the city. The numbers show the city’s middle class being hollowed out. Don’t tell Portland’s scabies-infested Occupy camp, but between 1980 and 2007, the share of wealth earned by Portland’s middle quintile declined by about 20 percent, while the top 1 percent’s share doubled. Increasingly, the only people who can afford to live in the city are the already-rich, high-density luxury condo dwellers or hipsters willing to slum it.

Fortunately for Portland, if there’s one demographic in America that can be counted on to issue a clarion call to help the working man in his hour of need, it’s urban progressives.

But seriously, you can forget the stark urban/rural divide: One of the major contrasts defining Portland is that between the new hipsters and the traditional working class. Most of the time the former are content passively to let their New York Times-approved politics and mores run roughshod over the latter, but once in a while the mask slips and the sneer is exposed. Here’s a choice bit from Willamette Week, the city’s hugely influential alt-weekly newspaper, about a spate of drownings in the city:

Every summer, some drunken red-neck drowns in the Sandy River, and local hand-wringers blame it on a lack of life-guards. The poor bastards who drown​—​rest their sloppy, Larry the Cable Guy-loving souls​—​don’t need lifeguards. They need high-school diplomas, shirts with sleeves, and the sense not to pound a case of Natural Ice and toss themselves off 30-foot cliffs into unscouted depths.

If the scenesters look down their noses at what’s left of the city’s strivers, the question is why? Portland’s working class is disappearing not because they’re competing for Darwin Awards, but because many of them have had the good sense to leave the city in search of well-paying jobs. Portland hipsters may feel good about having college diplomas, shirts with sleeves, exquisite taste in indie rock, and the savoir-faire to quaff generously hopped IPAs from the city’s 50 craft breweries. But education and taste haven’t left these purveyors of urban cool any better off financially than the middle and working classes they’re replacing. Maybe it’s all a plot so the last tribe standing can claim the remnants of Portland’s affordable housing.

Portlandia quips that “Portland is a city where young people go to retire,” and once again, the reality might be more extreme than the joke. In 2009, the Wall Street Journal reported, under a Portland dateline, that despite there being few jobs in the city, “the Hipsters just keep on coming.” The piece is worth savoring for its comically inane anecdotes about young Portlanders defining down what it means to “live the dream”: “He was attracted to [Portland’s] offbeat culture and hungered for change. Mr. Singer’s plan was to get an editing or writing gig at an alternative weekly newspaper. .  .  . Seven months later, the 26-year-old is still without a steady job.”

To the extent that the Journal tried to explain Portland’s appeal to young bohemians, it offered a “hard-to-quantify blend of climate, natural beauty, universities and​—​more than anything else​—​a reputation as a cool place to live.” In Triumph of the City, Glaeser makes a related observation​—​that modern cities must have “consumer” appeal. “Today,” he writes, “successful cities, old or young, attract smart entrepreneurial people, in part, by being urban theme parks.”

The idea of city-as-theme-park goes a long way toward capturing how Portlanders view their town. Consider this vignette from the introduction to Brew to Bikes: Portland’s Artisan Economy, edited by Portland State University associate professor of urban planning Charles Heying:

It’s Saturday morning and my granddaughter Sophie and I are heading to breakfast while her mom is at Pilates. We decide against Genie’s, our usual spot, where tattooed wait staff serve huevos rancheros and morning cocktails. We drive up Division Street looking for the place where we ate with her cousins, Emma, Hans, and Amelie, when they were in town. What was the name? It had those big sliding windows that opened to the street. We catch a glimpse of the retro chic Caffe Pallino as we drive by, but the traffic is moving us along so I am reluctant to stop. Sophie is disappointed. She won’t get her favorite dish, Bob’s Red Mill oatmeal with walnuts.

Brew to Bikes attributes the fact that breakfast in Portland is a dizzying array of sophisticated consumer options to “local self-reliance, sustainable living, and the integrity of craftsmanship.” While it’s hard not to root for entrepreneurial initiative wherever you find it, in Portland it carries a whiff of desperation. I submit that the real reason Portland has a thriving artisanal economy is that the regular economy is in the dumps. Portland’s hipsters are starting craft businesses in their garages and opening restaurants not merely because they “reject passive consumption” but because they can’t find jobs, the kind that offer upward mobility. If there’s a more rational reason why a small city like Portland has 671 food trucks, I’d love to hear it.

But let’s not get carried away with the idea of Portland as America’s hipster theme park; the analogy is spectacularly off in one crucial way. Theme parks are sanitized, family-friendly environments. Portland, by contrast, has become a decidedly immoral place.

I’m well aware that the one unforgivable sin among America’s enlightened urban liberals is to be a moralizing killjoy. But since I’m already out on a limb complaining about Portland’s lack of laissez-faire economic policies, I’ve little to lose by complaining about its laissez-faire approach to civic virtue.

If you don’t think this is a problem for Portland, I invite you to hang out in the parking lot at Pussycat’s Puffing Palace at 11 a.m. on a Thursday and tell me you don’t feel a bit scuzzy. Pussycat’s Puffing Palace is just a few doors down from the Vegas VIP Room and a bit further down the street from Secret Pleasures. I was there to meet Lisa Leithauser of SOS Oregon, a group dedicated to “work[ing] with cities and counties to establish simple basic zoning laws, and to enforce these laws for all businesses.” Leithauser refers to this stretch of Southwest Canyon Road in the Beaverton suburb as the “Tour de Porn.”

The statistic that gets tossed around a lot is that with its 56 strip clubs, Portland has the most per capita of any major city in America. I have no idea whether that’s accurate​—​much to the relief of many reading this, the sex industry is not a font of detailed information about its business practices​—​but it could well be. For a frame of reference, Las Vegas has around 30 strip clubs and Seattle has 4.

It may seem bizarre that this state of affairs exists in a place that’s all too willing to scare off employers and developers. But to some extent it’s out of the city’s hands.

In 1987, an Oregon Supreme Court case involving an adult bookstore established, according to the New York Times, a “doctrine of total freedom of expression [that] differs from Federal standards that have developed on the assumption that suppressive laws may apply to obscenity.” In 2005, the Oregon Supreme Court extended the right to free expression to live sex shows. In Oregon, your right to open an adult business trumps nearly every other legal and civic concern.

Portland may be at the mercy of state law here, but it’s hard not to credit also the city’s cultural and political transformation of recent decades. Like it or not, strip clubs are now part of the warp and woof of a city without a lot of strong countervailing moral institutions​—​a 2010 Barna report listed Portland as the city with the third-lowest church attendance after San Francisco and Portland, Maine. In addition, Leithauser suggests, “there’s a faction of people in Portland that think it’s cool to have a strip club in their neighborhood.”

Exhibit A is a joint called Casa Diablo​—​Portland can proudly claim the world’s only vegan strip club, where the women are treated like pieces of .  .  . oh, forget it. I drove by Casa Diablo, a dilapidated-looking roadhouse in industrial northwest Portland. Depressing as it was, I noticed it’s a roadhouse with a large patio​—​in Oregon, it may be your constitutional right to open up a sex shop next to a school, but when it comes to free expression, smoking indoors is a bridge too far.

In interviews, the owner of the club, Johnny Diablo​—​I’m guessing he acquired the moniker when he sold his soul to rockabilly​—​is more eager to peddle his “ethical veganism” than flesh. “My sole purpose in this universe is to save every possible creature from pain and suffering,” he told, yes, the New York Times. According to Willamette Week, he lectures dancers who show up for work wearing animal products about “not bringing murder victims into the establishment.” But despite Mr. Diablo’s commitment to ending suffering, many of Portland’s feminists and vegans have gone on record as being less than happy with the message sent by his Casa.

While problems attend Portland’s strip clubs​—​at least one major owner of clubs is under federal investigation​—​they’re not the main issue in the city as far as Leithauser is concerned.

Pussycat’s Puffing Palace, the Vegas VIP Room, and Secret Pleasures aren’t strip clubs per se. They’re a species of adult business unique to Portland called “lingerie modeling” shops. The customer enters, pays his money, goes into a private room with a girl, and what happens from there .  .  . well, it’s not usually full-blown prostitution. They are known around town as “jack shacks.”

Leithauser isn’t some crusading Bible-thumper who wants to rid Portland of wickedness. She’s a typical Portland mom in a rain jacket and yoga pants who had the misfortune of living a few blocks away when Secret Pleasures moved into the neighborhood. This is not skid row​—​a jack shack landed in the middle of suburbia, across the street from a car dealership. Residents got tired of driving by and seeing the blind-drunk clientele urinating in the parking lot in the middle of the day.

Then just down the street, a stray cigarette from one of the girls on the patio at Pussycat’s turned the place into a tinderbox. Like a lot of these establishments, it was operating in an old, poorly maintained building​—​a stone’s throw from a tract of suburban homes.

Leithauser managed to shut down Secret Pleasures, in part by convincing the Jiu Jitsu dojo in the next building to install a camera with a live Internet feed pointed at the door. The Vegas VIP Room is still operating.

It might be foolish to expect that Portland could or even should try to stamp out adult businesses. But on behalf of SOS Oregon, Leithauser finds herself speaking out for people from across the city unhappy about similar neighborhood nuisances. She admits she’s a bit exasperated that her life is now consumed by regular dealings with strippers, club owners, and, worse yet, politicians. (She also spends time working with a local nonprofit that helps special needs kids.)

Attempts to modify the state constitution to bring it more in line with the First Amendment have been stymied in the Oregon legislature. But Leithauser thinks the city might do more. “I think it’s reached a little bit of a breaking point because it’s starting to affect business,” she says. Recent reports that Portland is a hub of sex-trafficking have left local politicians less indifferent than usual.

Still, Portland-area residents have been grappling with this problem for years, with little to show for it. Ultimately, Leithauser sees this as an indictment of the whole city, with its “culture of ‘let’s look the other way.’ ” I ask her if, besides the surfeit of poorly regulated adult businesses, there are other examples of Portland’s willingness to sweep problems under the rug. Leithauser ticks off a list of names: Sam Adams, David Wu, and Neil Goldschmidt.

My own willingness to tolerate Portland’s dysfunctional civic culture reached its limit with the election of Sam Adams as mayor. A former city council member, an openly gay man, and a proselytizing bike commuter, Adams hit the sweet spot for Portland’s electorate. All those excited about an agenda of not paving roads and using tax dollars to pay for city employees’ sex change operations cast their votes accordingly.

But none of that is the real problem with Sam Adams. In 2005, Adams, who was then 42, met a 17-year-old boy interning in the state legislature with the unfortunate name of Beau Breedlove. The official version of events is that Adams was mentoring Breedlove. They were known to go out to dinner alone, and Adams even attended Breedlove’s 18th-birthday festivities so Breedlove could “show his family that it’s possible to be gay, successful, and happy,” according to the Oregonian.

Fast-forward to 2007, when Adams is running for mayor. The Democratic primary heats up, and one of his opponents accuses Adams of having an inappropriate relationship with Breedlove. The denunciations of the charge come fast and furious. Adams’s surrogates suggest that homophobia is driving this assault on his character. Adams wins the primary and is elected mayor in 2008 with 58 percent of the vote.

In January 2009, just as Willamette Week is about to break the story, Adams finally admits that, yes, he had a sexual relationship with Breedlove and, yes, he lied about it aggressively. Adams insists the sexual relationship didn’t begin until the summer of 2005, after he presented himself to Breedlove’s family as a role model at the 18th-birthday party in June.

“I didn’t believe that given the way that rumors were being spread​—​about whether I had broken the law by having sex with a minor​—​that people would believe me,” said Adams, explaining that he had no choice but to lie. Despite this self-serving admission, the state attorney general cleared him of wrongdoing. During the investigation, not a single witness was put under oath.

Adams has since survived two recall attempts, and lately has had a recurring role on Portlandia playing the assistant to the mayor​—​who in turn is played by Twin Peaks actor Kyle MacLachlan. Portlandia even had a series of sketches about the mayor hiding a dark secret. It turned out that the mayor was playing bass in a reggae band, something that would really outrage his indie-rock-loving constituents.

The next mayoral election is in May, and Adams has mollified some of his critics by declining to run again. But if past is prologue, he is unlikely to be drummed out of Oregon politics.

Which brings us to David Wu, the former congressman from Oregon’s First District representing Portland. In 2004, three weeks before the November election, the Oregonian reported that Wu had been credibly accused of rape while an undergraduate at Stanford. Wu responded by threatening to sue the Oregonian and its source. Portlanders elected him to Congress three more times.

After years of rumors about his erratic behavior, Wu resigned last year after he had an “aggressive, unwanted sexual encounter” with the teenage daughter of a political donor, according to the Oregonian. In the special election to replace him in January, Portland voters elected Democrat Suzanne Bonamici. She is the wife of Wu’s personal lawyer, the man who threatened to sue the Oregonian for reporting the prior allegations of rape.

But neither Wu nor Adams can top former Portland mayor and Oregon governor Neil Goldschmidt for sheer moral turpitude. Even apart from Wu’s difficulties, 2004 was a banner year for Oregon sex scandals, and once again Willamette Week had the dirt. While Goldschmidt was mayor in the 1970s and ostensibly hard at work bringing light rail and other innovations to Portland, it turns out he was also having sex with a 14-year-old babysitter.

Goldschmidt claims the relationship lasted “nearly a year,” but Willamette Week reports it lasted three years, until the girl was 17. It was also revealed that he decided against running for a second term as governor in 1990 because he was afraid the story would become public as part of a court dispute. Willamette Week further established that “dozens of Oregonians​—​many of whom today work at the highest levels of business, government, and the media​—​knew something about Goldschmidt’s secret” and kept quiet for 30 years. Goldschmidt had been allowed to keep more or less running the state at least in part because he was enriching many of the people who knew what he was hiding. Luckily for Goldschmidt, the statute of limitations had expired by the time all this became public. Other-wise, under Oregon law he could have been convicted of third-degree rape and forced to register as a sex offender. Last year, they finally took the former governor’s portrait off the wall of the state capitol “out of respect” for his victim, according to the spokesman for Oregon’s senate president.

Just to bring the story full circle, Sam Adams would later tell Out magazine that Goldschmidt’s “swift public condemnation weighed heavily” in his decision to lie about his own conduct. He needn’t have worried. By the time Adams’s scandal rolled around, four years after the Goldschmidt revelations and initial Wu allegations, Portland voters were inured to this kind of thing.

If local political news has been dreary in recent years, and the glut of national coverage has been so glowing as to put Portland residents in the unusual position of complaining about it, well, let me say to them​—​you’re welcome. And I’m not the only one who’s sick of Portland hype.

Last summer, a lengthy New York Observer story quoted several residents of Brooklyn bemoaning the “Portlandification” of their fair borough. As anyone who’s ever been to a loft party in bourgeois Williamsburg can attest, you’re likely to end up gritting your teeth as the guests rail against corporate personhood and explain the aesthetic imperative behind the latest exhibit to smear body fluids on canvas. If you could find a defense of Portland’s runaway progressivism and hipster culture anywhere in America, you would think it would be Brooklyn. But the Observer had no trouble finding Brooklynites ready to sneer that the importation of Portland’s artisanal culture would make Brooklyn “precious” and, worse, that Portland was “Brooklyn without black people.” (It is, in fact, America’s whitest city.)

In January, the Washington Post officially declared Portland “out” and Pittsburgh the new hotspot. “Portland has overextended its welcome as the destination for hipsters who want to find themselves, while frolicking in beautiful scenery and reasonable rents,” pronounced Post writer Monica Hesse. “Pittsburgh is reasonable-rents, nice scenery, nice downtown, and the people are, in general, just far less insufferable.” If Portland stops receiving so much favorable media coverage, maybe the progressive politicians and urban planners will fall out of love with it as well.

In the meantime, there’s still a lot to like about Portland. But as a former resident I feel compelled to deliver this message to the city’s current inhabitants: Stop reading the New York Times, roll up your sleeves, and fix your city.

It’s getting embarrassing.

Mark Hemingway is online editor at The Weekly Standard.

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