Newspaper's black-bag job fixed election for Portland mayor

Late on the evening of June 2, 1917, the Portland Morning Oregonian sprang a trap – a cunning and dirty trap.

The always-formidable daily newspaper, owned and edited by Henry Pittock following the death of the legendary Harvey Scott, had thrown its weight behind a big, boisterous City Council member named George Baker in the race for Portland city mayor. But in a fierce race with Union man and small-business owner Will Daly, Baker was clearly on track to lose.

For Pittock, that was simply not acceptable. Daly, a former Oregonian employee who had gone on to become Portland's utility commissioner, had earned Pittock's lifelong hatred several years before, when he'd uncovered a secret contract between the city and Pittock – under the terms of which, in exchange for favorable press in the Oregonian, the city would install (at considerable expense to the taxpayers) a half-mile-long pipeline bringing unlimited quantities of complimentary Bull Run water out to Pittock's West Hills estate, which was outside city limits.

When Daly publically exposed this larcenous little scheme, Pittock's personal reputation was considerably sullied, and Daly instantly became his ex-boss's bête noir. No, Pittock would not sit idly by while his number-one enemy took over the city government. But then, he wouldn't have to. He'd already taken the necessary steps to make sure that didn't happen.

Some time before this, Pittock had sent some of his more morally flexible staff members on what you might call an undercover investigation. You might also call it, as Watergate plotter E. Howard Hunt surely would, a "black bag job." Simply put, they'd broken into Daly's house and rifled through his papers, looking for something they could use.

They'd hit the jackpot.

What they had found was a partially-filled-out application for membership in the Socialist Party, dated 1910.

It isn't clear, even today, whether Daly ever actually joined the Socialist Party. Some sources say he did, briefly, before renouncing it and registering as a Republican; others say he never sent the paperwork in. But such niceties didn't matter to Pittock. What he cared about was not fairness or journalistic integrity, but simply denying Daly the mayorship. And now, two months after U.S. entry into the First World War, the anti-war Socialist Party was extremely unpopular. A credible claim that Daly was a registered Socialist would be some serious medicine – maybe even an election swinger if he handled it right.

And Pittock intended to handle it right. He sat on the document until the very last minute. Then, on the evening of June 2, he loaded the next day's Oregonian up like a cannon with the fruits of his felony and pulled the trigger. The shot hit the front porches of most homes in Portland the very next morning, the day before Election Day.

"SECURITY OF CITY HANGS ON ELECTION!" it shrieked, in heavy headline type on Page One. "Baker and Growth or Daly and Strife (is the) Issue. QUESTION IS UP TO VOTERS. Daly's Election First Number on Radical Programme. AGITATORS ALL BACK HIM!"

Such was the Oregonian's reputation as a voice of establishment cronyism that even this massive editorial broadside, delivered as it was the day before election (guaranteeing that Daly would have no chance to respond in any meaningful way), didn't move the election results much. But it changed enough minds to hand Baker the election, by a slim 1-percent margin.

And just like that, Daly was finished.

* * *

Will Daly was born in Missouri and was one of those newspaper pressmen with ink in their blood. He started work at the Springfield Leader-Democrat at age 10 and by the time he was 31, he'd worked his way to the top – he was the press foreman there.

When his mother died, Daly and his wife Daisy moved to Oregon, and Will ended up taking a job working on the press at the Morning Oregonian a few months after arriving; a few years later, he moved on to the Portland Linotype Company. He also opened his own small printing business on the side, the Portland Monotype Company.

Meanwhile, Daly was also rising through the ranks at the Oregon State Federation of Labor. By 1908 he was the union president. As an articulate, intelligent fellow who was both a blue-collar worker and a small-business owner, he turned out to be remarkably effective at helping Union workers and small-scale entrepreneurs see eye to eye. That was especially true after he was elected to the City Council in 1911.

This, of course, made him somewhat dangerous to the large-scale former entrepreneurs who formed Portland's power elite, including the fairly scurrilous one for whom Daly had once worked – that is, Pittock. So it was probably inevitable that Daly and his ex-boss would stop seeing eye-to-eye pretty quickly.

Things got bad in 1914 when Daly went to bat for the drivers of "jitneys" – which were like the progenitors of taxicabs. Jitneys were privately owned automobiles that entrepreneurs would buy and then drive around town, looking for fares. This was annoying the executives of the Portland Railway, Light and Power Company, the monopoly outfit that controlled Portland streetcars, which wanted the jitneys outlawed. Pittock, who probably regularly enjoyed brandy and cigars with the PRL&P bigwigs, vigorously agreed and never lost a chance to make the case that letting these small-time businessmen continue providing service threatened to destroy the city's massive electricity-and-transportation monopoly. Daly just as vigorously disagreed.

Then came that incident with Pittock's attempted theft of city water.

* * *

After losing the election, Daly retired from public life and focused on his printing business. In 1920 he accepted an appointment as Oregon's federal food price commissioner, but when he learned how much red tape and scrutiny of his business was involved, he resigned. And when Mayor Baker stood for re-election that same year, Daly actually endorsed his onetime rival.

He died, mostly forgotten, in 1924, just 54 years old.

(SOURCES: Johnson, Robert D. "The Myth of the Harmonious City," Oregon Historical Quarterly, fall 1998; Daley, Shawn. "Will Daly (1869-1924)," Oregon Encyclopedia, oregonencyclopedia.org; Portland Morning Oregonian, June 3, 1917)

Finn J.D. John teaches New Media at Oregon State University and is the author of "Wicked Portland," a book about the dark side of Oregon's metropolis in the 1890s. He produces a daily podcast at ofor.us/p . To contact him or suggest a topic: [email protected] or 541-357-2222.