Much of the Oregonian ’s readership resided in Portland, Oregon’s most populous city and the seat of the paper’s headquarters. Portland’s metro area was home to nearly half of Oregon’s residents. [1] City voters tended to lean left; one conservative commentator mocked typical political views in Portland as covering “the full range of opinion from left, to far-left, to ultra-left.” [2] The political dynamic in the rest of the state was somewhat more complicated. In 2009, four out of Oregon’s five congressional representatives were Democrats; two Democrats represented the state in the Senate. The state’s electoral votes had gone to the Democratic presidential candidate in every election since Republican Ronald Reagan had won the state twice in the 1980s. But Democrats Al Gore and John Kerry, who ran for President in 2000 and 2004 respectively, each won Oregon by thin margins of only a few thousand votes. The state’s Senate seats had been split—one Democrat and one Republican—for some 10 years until Gordon Smith (R-OR) lost his seat in the 2008 election. Democratic dominance in Oregon was by no means assured.

The Oregonian editorial board did not strive to reflect the views of its politically diverse readership, but rather to inform them. Reader interpretation of the board’s editorial slant varied along with political preference. Caldwell says:

I think the general reader would see us as a little bit center left. I think that many Portland, especially Portland central city readers see us as center right, but I think that’s partly because the politics of Portland tend to be [liberal].

Political scandals. Sex scandals were not unknown in Oregon politics. Caldwell himself had helped the Oregonian cover at least two others involving public figures, once in the news section and once at the helm of the editorial board. In 1992, when Caldwell was the Oregonian ’s Metro news editor, the Washington Post broke the story that 10 women had accused Senator Bob Packwood (R-OR) of sexual harassment. The Oregonian news section was widely criticized for failing to get the story first; the incident even inspired a briefly popular bumper sticker: “If it matters to Oregonians, it’s in the Washington Post .” [3] Caldwell had, in fact, assigned a reporter to look into rumors about Packwood’s sexual impropriety before the story broke, but the Post published first. The Oregonian was further embarrassed when it later came out that Packwood had forced a kiss on one of its own political reporters, though Caldwell had not been informed.

In May 2004, Caldwell and the Oregonian again faced a sex scandal involving a state politician—and again another newspaper broke the story. This time, an investigative reporter at alternative weekly Willamette Week discovered that former Oregon Governor Neil Goldschmidt had had an affair with his children’s then-14-year-old babysitter in 1975. At the time, Goldschmidt had been 35 and Portland’s mayor. [4] While the news section scrambled to catch up with Willamette Week ’s scoop, the editorial board, now under Caldwell, wrote:

It is beyond sad to see former Gov. Neil Goldschmidt’s remarkable service to Oregon end this way, with a brilliant public man brought down by a stunning personal failure nearly 30 years ago. [5]

In the week that followed, the Oregonian was deluged with reader letters on the Goldschmidt affair. Many condemned the Oregonian ’s editorial as far too supportive of Goldschmidt. Under Oregon law, sex with a minor under 16 was third-degree rape, punishable by up to five years in prison. But the three-year statute of limitations for prosecuting the perpetrator of such a crime had long since passed; Goldschmidt had gotten away with it. One reader wrote:

The Oregonian editorial board has gone too far… The board… tries to make excuses, tries to put a “human face” on Neil Goldschmidt… Goldschmidt raped a child. He is a sexual predator. [6]

Another reader theorized that the Oregonian would have been far harder on Goldschmidt had his victim been a boy. [7]

Gay marriage. Nor did Caldwell lack experience commenting on the politics of homosexuality. In 2004, a county commissioner with jurisdiction over Portland assigned a state attorney to review the Oregon constitution to determine whether it permitted gay marriage. The attorney found that denying marriage licenses to same-sex couples constituted unconstitutional discrimination on the basis of sexual orientation. The county commissioner ordered courthouse clerks to begin issuing marriage licenses to same sex couples immediately.

Caldwell and most of his editorial board colleagues found the move unwise. Board members had differing opinions as to whether gay marriage itself should be legal. The board officially embraced civil unions—same-sex partnerships that carried many of the legal benefits of marriage but stopped short of the title. In the editorial he wrote on the matter, Caldwell decided to sidestep the desirability of gay marriage itself, instead blasting what he saw as the county commissioner’s undemocratic intervention in an issue that should have been left to Oregon’s voters. Caldwell also warned that the commissioner’s decision risked sparking an anti-gay backlash that would ultimately set back the cause of legalizing gay marriage. He did not ask the commissioner to resign, but suggested that voters recall her and several of her colleagues, concluding:

If they can't be trusted to make a momentous decision in an open, fair, respectful and transparent manner, they shouldn't be trusted to direct the daily operation of county government. [8]

That winter, as Caldwell had foreseen, Oregonians overwhelmingly passed an amendment to Oregon’s constitution that banned same-sex marriage outright.