Portland Before It Was Portland: The Dark Side of the City of Roses


In February 1957, two reporters inaugurated the Senate Select Committee on Improper Activities in the Labor or Management Field by exploding the reputation of Portland, Oregon; instead of the sleepy frontier city people had imagined – if they had any conception of the city at all – the Portland that emerged from the testimony was infested with prostitution and gambling, overseen and coordinated by a craftily constructed alliance of organized crime, the Teamsters Union, and local politicians. Thomas Donnelly focuses on this era of Portland’s disreputable past in his analysis Dark Rose: Organized Crime and Corruption in Portland. What emerges from his narrative of the city’s struggles with organized crime – and the local business and political leadership’s complicity with it – provides a stark contrast with Portland’s current mythology of itself as an urban utopia. Portland’s contemporary status as a progressive stronghold among American cities may be well-earned, its “livability” a function of its grassroots, neighborhood-based activism, environmentalism, mass transit, and Urban Growth Boundary and other legacies of the 1960s and ’70s; what Donnelly’s narrative provides is an important corrective to notions of the city as a timeless, untroubled oasis of liberalism.

Donnelly situates his story at the intersection of multiple streams of national experiences, including the histories of American cities, the intertwined relationship of organized crime and labor, and the specifics of Portland itself. Dark Rose performs a delicate balancing act, then: Donnelly casts Portland as both representative of these larger national dynamics and as an deviation from them, as both an example and an exception. For Portland to be worthy of study, then, it can not simply be just another city whose “demonstrated patterns of vice and corruption” are “consistent with those present in in larger U.S. cities” (5); for Donnelly, the particulars of Portland’s “exceptional case study” also demonstrate the ways in which the city may be different from the norm, especially in the unique circumstances of its vice and corruption’s resilient resistance to the best efforts of progressive reform (5).

To help ground the the specifics of Portland’s exceptionalism, Donnelly contextualizes the scandalous events of the 1950s by briefly detailing their specific, particular antecedents. Donnelly conducts a chronological survey that leans heavily on the work of Portland historians Carl Abbott, Jewel Lansing, and E. Kimbark MacColl, synthesizing these secondary sources (among others) into a tale that casts Portland as a boomtown characterized by simultaneous waves of criminality and economic growth. By the 1880s, the growth spurred by east coast elites’ investments in the lumber and Willamette River-based shipping industries brought many men looking for work to its environs; as happened in other cities, this influx of laborers “stimulated the construction of saloons, dancehalls, and brothels where men indulged in various ‘sinful’ pleasures” (26). The city’s business elites profited not only from their legitimate enterprises, but by providing utilities, maintenance contracts, and real estate, they saw returns from the rapid increase of disreputable ones as well; having hands in two pockets of Portlanders, then, the business community was “disinclined to stifle the profitable gambling, liquor, and prostitution operations that reformers wanted to eliminate” (27). Portland’s rampant vice was often met with several Progressive attempts to reform the local government’s cozy relationship with criminality; as one example among many, Donnelly cites the efforts of Mayor Harry Lane, a Democrat who successfully ran against the Republican machine in 1905 on “a platform supporting the working class and … [opposing] corporate interests and political corruption” (38). While Donnelly notes that Lane’s administration is remembered mostly “for its fight for morality and humanity” (38), it is probably more noteworthy that it was ineffective; its “meager results,” undermined by a city council that would simply reverse his vetoes, made “clear that big business and political bossism ruled the city” (39). Joe Simon, Lane’s successor after the election of 1909, quickly worked to unfetter the liquor trade and lift restrictions that curtailed the prostitution businesses, returning the city to (scurrilous) business as usual. In his campaign against Harry Lane, Thomas Devlin sloganeered that “The reformer ultimately fails” (38; Donnelly cites Lansing’s ”Portland” as the source); while Devlin lost his race, his prophecy seemed to be accurate, as Progressive reforms never seemed to take hold in the city, allowing vice to fester until the middle of the 20th century.


The primary focus of Dark Rose – the interaction of Portland’s political and vice interests with a new player, the Teamsters Union – begins in the post-WWII era. As Donnelly explains (citing both the Portland City Club’s introspective report Conscience of a City and Gardner and Olson’s study of urban corruption, Theft of the City), unlike other cities whose corruption diminished with the repeal of Prohibition and the introduction of the New Deal, Portland’s vice industries grew dramatically in the run-up to the war, bucking the national trend and becoming better organized, concentrated and efficient. The war itself spurred a massive growth spurt in Portland’s population, thanks to its pivotal role in the shipbuilding industry; as Donnelly notes (citing Abbott), the rapid influx of young men who came to work in the booming Portland economy also fueled the vice industries, who were eager to relieve them of their wages. The political leaders of the era – Mayor Earl Riley and Police Chief Lee Jenkins – believed that “a policy of toleration and cooperation in Portland was easier to administer than trying to police the illegal activities all over the city” (57), a policy made even more convincing by the graft proceeds that made their way into their pockets (Donnelly quotes MacColl’s suggestion that Riley took in $60K per month in protection money and kept the sum in a safe in his office at City Hall!, 58). More importantly for the unfolding of the Portland ’50s scandal, though, was the introduction of a self-appointed “vice czar” (60) into the mix, a bootlegger and brothel owner who stitched disparate gambling parlors, pinball machine halls, shady bars, and whorehouses into an empire. Expertly distributing graft among police and politicians while strong-arming those who would challenge his authority, James Elkins emerged in the late 1940s as the focal point of Portland’s vice and corruption.

The bulk of Dark Rose concerns itself with Elkins’s domination of Portland’s vice industry, his mastery (and corruption) of local politics, and his response to the Teamsters’ decision to move into Portland and take over his racket. Donnelly’s account becomes more compelling, robust, and distinctive as it circles its main interest: Donnelly leaves much of his reliance on secondary sources behind as he turns his narrative towards Elkins, employing impressive investigative chops in his sifting through 1950s Oregon newspaper accounts, municipal legal proceedings, Congressional testimony, FBI and police reports, wiretap transcripts, and personal interviews with some of the story’s key actors (including Wallace Turner, one of the two reporters who broke the story in the first place). What emerges is a detailed, methodical chronology of the events that brought Portland to the attention of Congressional inquiry, convincingly revealing a city overrun with organized crime and political corruption.

As Donnelly carefully details, Elkins pursued a two-prong approach to running Portland’s vice. Politically, he orchestrated payoffs and kickbacks to “every level of city government” (63), extending his reach by bribing local law enforcement and financing the election of representatives small and large (including the mayor himself, Fred Peterson). As a criminal entrepreneur, he employed a scam that assured him a monopoly: he would “authorize” aspiring racketeers a franchise into his gambling or prostitution networks, offering protection from The Law’s interference in exchange for a weekly payoff. After a while, though, he would coordinate police raids that would temporarily shut the criminal businesses down, strangling the local operator’s profits; after several repetitions of payoffs-and-shutdowns, the frustrated would-be entrepreneurs would be forced to abandon their operations, leaving Elkins with new, uncontested revenues and profits. Once Elkins established his rhythm of hostile takeovers of local criminal businessmen, his criminal empire paced the growth of the booming city itself; because of the time-tested tolerance of graft and political corruption that Donnelly documented earlier, Portland’s citizens rarely rebelled against its criminal element (a crusading anti-crime mayor, Dorothy McCullough Lee, was elected to one term in 1948, but the city’s business elites effectively squelched her efforts at reform, leaving her to be defeated by her crooked successor Peterson in 1952). By the mid-1950s, newly affluent Portlanders fled for the suburbs on the east side of the Willamette leaving the crime-ridden central city behind to fester, ignoring the efforts of crusading reporters and reformers; as Donnelly explains, “Elkins and other vice racketeers were generally successful because most Portlanders simply did not care” (72).

One group of people who did care about the rise of organized, rationalized, efficient crime in Portland, though, was the unscrupulous, power-and-revenue-hungry leadership of the Teamsters Union. Seeing an opportunity in Elkins’s one-man control of the city, the Teamsters began to try to apply their organizational strong-arming to its gambling and prostitution industries. In an elaborate scheme, the Teamsters’ official Clyde Crosby met with Elkins and William Langley, a local lawyer who aspired to become Portland’s District Attorney; after maneuvering Langley into office, the Teamsters and Elkins were in position to make Portland’s rackets more efficient than ever. Elkins rightfully sensed that he was destined to be squeezed out by the powerful union, though; laying a trap for both the union and local law enforcement, Elkins secretly taped hours of conversations between his Teamster collaborators, DA Langley, and scores of other criminals and local officials. Rather than see his foes succeed in dethroning him, Elkins went public and brought his recordings to reporters at the daily Oregonian – and the story became a local sensation. The scandalous, sensational headlines ultimately reached eastward to Washington, where Senators John McClellan and Robert Kennedy were collecting evidence in their mounting investigation of union racketeering; upon visiting Portland and learning about the depth of the scandal first-hand, Kennedy decided that the Portland story would be “crucial” to their case against union racketeers in the larger cities of New York, Detroit, and Chicago (129). The McClellan Committee ultimately called nearly two dozen witnesses from Portland between 1957 and 1960, including Elkins, Langley, and Crosby as well as the newly elected – and scandal-scarred – mayor, Terry Schrunk. Before the Committee adjourned, Portland was laid bare as a city struggling with organized crime, its parade of criminals providing “the crucial evidence for the committee to link the Teamsters with municipal corruption and organized crime” (143).

What were the net effects of the Portland Vice Scandals? Donnelly’s analysis is both illuminating and frustrating, the “moral” of the story unsatisfying and its narrative anticlimactic. While one might think that the city would be chastened or humbled – Senator Karl Mundt believed that the “people of Portland” would be embarrassed to have a “mayor who flunks a lie-detector test and a district attorney hiding behind the Fifth Amendment” (144, from the McClellan Committee hearings) – the opposite appeared to be the case, with many Portlanders rejecting the Committee’s findings as a “witch hunt” (145). Mayor Terry Schrunk, whom the committee strongly suggested was tied to Elkins, found himself accused of corruption back home, with no less a luminary than Robert Kennedy testifying against him; RFK’s celebrity did not sway the courtroom, though, and – failed lie-detector test be damned – Schrunk was exonerated. Schrunk became one of the city’s more popular mayors, serving four terms (1957-1972), while being, in Donnelly’s estimation, ineffective. On Schrunk’s watch, “no changes were made to Portland’s model of municipal government” (149); having become gun-shy after his legal difficulties, Schrunk governed conservatively, making him less like the “great mayors of the 1950s and 1960s” like Philadelphia’s Clark or New York’s Lindsay (150), and more representative of “the political consensus of the 1950s” (150, Donnelly quoting Abbott). Three different Portland grand juries issued 115 indictments between 1956 and 1957; ultimately only Langley, Elkins, and one of Elkins’s lieutenants were found guilty (152; a madam was fined $250 too), with Langley’s punishment being only a $428 fine. Donnelly maintains that “Portland provides the basis for a broader understanding of issues of urban corruption and crime in American cities” (162), and his belief that the city’s vice scandal provides “incredible insight into how labor, business and government operated in the ‘open city’ of the twentieth century” (162) seems well-founded by his detailed, revealing expose; unfortunately, the conclusion that “Beneath all the lovely lawns and rose gardens there was an immense amount of corruption” (Donnelly quoting Turner, in an interview, 162) leaves readers with a murky, melancholy inconclusiveness. Donnelly ends his Portland expose with Schrunk entrenched in office and a semi-retired Elkins killed in an Arizona mysterious auto accident in 1968. Donnelly does not walk readers from Schrunk’s water-treading leadership to that of his successor, “great mayor” Neil Goldschmidt, the trailblazing progressive leader (and future Oregon governor) who was among the critical factors leading to Portland’s current reputation as a mecca for community involvement, ecological foresightedness, and visionary mass transportation; readers curious as to how the city might have lurched from one extreme to another are best served by turning towards Abbott and Lansing themselves. Donnelly also does not use the example of the ’50s vice scandals to suggest a continuity with more contemporary scandals, such as Goldschmidt’s well-guarded statutory rape scandal (a secret kept quiet for decades, in part, by the Oregonian), Sam Adams’s 2007 sex scandal, or the workplace-infidelity scandal within the city’s Health Department of the summer of 2013; interested readers might want to turn through the archives of Portland’s alternative weeklies for more details of those events, and reach conclusions of their own. In Portland — if not other cities — progressivism does not seem to preclude scandalous behavior from elected officials; Devlin’s ominous warning of “The reformer ultimately fails” is what haunted this reader upon closing Dark Rose.

Donnelly’s book is a provocative, rigorously researched treatment of the interaction of crime and corruption in Portland, and, along with Phil Stanford’s journalistic, noir-inflected Portland Confidential and Finn J.D. John’s fun, “lusty” collection of late 19th and early 20th century anecdotes Wicked Portland, makes a worthy addition to the growing library of works dedicated to detailing the seedier side of Portland’s past.

Phil Oppenheim worked for twenty-five years in the trenches of network cable television, culminating with his role as SVP of Programming for TNT and TBS; more recently, he has joined the growing army of cord-cutters and cord-shavers in exploring the newer world of digital entertainment platforms, currently serving as the Chief Curator for the Comic-Con Subscription-Video-on-Demand service (launching in 2016). He is also working on a doctorate within the Department of Radio-Television-Film at the University of Texas-Austin, focusing his studies on fringe broadcasting phenomena of the 1950s.