It looks like we’re about to enter another cycle of ballot measure warfare in Oregon.
From the mid-1990s through the early 2000s, Oregon voters confronted dozens of initiatives on every general election ballot, most of them devised to advance a limited-government, low-tax and anti-union agenda championed by Republican Bill Sizemore and a handful of big donors.
Now another Sizemore-like effort is being launched by a new crop of big donors, combining tax-cutting targets with proposals to loosen government regulations, promote government accountability and, in a populist twist, ban both union and business contributions to candidates. Their agenda is now on full display in 11 different ballot initiatives filed last week for the November 2026 election.
You can find these initiatives on the Secretary of State’s website, listed as Initiative Petition 57 through 67. All are sponsored by John von Schlegell, managing director of Endeavour Capital, a Portland-based investment firm.
If there is one throughline in the array of these initiatives, it’s that they all challenge the record of Salem’s governing coalition — taxing business and the wealthy to raise more funding for education while failing to boost student achievement or make progress on worsening problems like homelessness and drug addiction.
Like Sizemore, von Schlegell and his team want to limit taxes. But their approach to government looks more like a course correction than a frontal assault — accelerating timelines for issuing permits, posting school accountability reports, requiring judges to appoint public defenders rather than dismissing charges and adding land within urban growth boundaries. These are proposals to clear the cluttered political pathways that have stymied problem solving on many fronts
As with Sizemore decades ago, this appears to be part of a plan to set agendas and challenge a governing consensus on a range of cherry-picked issues over multiple election cycles. Progressives should recognize that this will not likely be a one-and-done threat to their political standing.
The question now is how Democrats and their labor allies in Salem will respond. Will they tack to the center on any of the policies on von Schlegell’s target list and perhaps refer compromise alternatives to the ballot? Or will they double down in defense of their policies?
In what is expected to be a blue wave election in 2026, the Democratic leadership and their union allies may relish another “fight back” campaign. After all, when Sizemore’s operation collapsed and he ended up in jail, public sector unions in Oregon inherited a fundraising operation that, on a per capita basis, generated more member donations for politics than their counterparts in any other state in the nation. And that financial advantage gave them the seat at the head of a broadening coalition table that shaped Oregon’s progressive agenda for almost two decades. Why retreat now?
Well, that was then. It’s hard to see how progressives can tap any new sources of political capital now, beyond what they’ve already brought to the table.
And, there are lessons to be remembered from the decade of “ballot measures gone wild” that Sizemore inaugurated.
For one, Sizemore pioneered the technique of working the system to gain winsome ballot titles for his proposals, giving him the pole position in the campaigns that followed and forcing his opponents to spend heavily to overcome that advantage.
Also, Sizemore had some wins, most notably when he won voter approval in 1996 for a limit on property taxes that remains in effect today.
Finally, even when he lost, Sizemore would brag about putting his opponents on the defensive, and it took years for public sector unions and their allies to turn the tables on him.
For their part, Von Schlegell and his team may feel confident that now is the time to force a reckoning with what they see as the failures of the tax-and-spending policies of the Democratic coalition. They may think that whatever they take to the ballot will tap into voters’ frustration with a high-cost governing strategy that has delivered poor results.
But timing is another matter when it comes to the economy. Sizemore’s anti-tax crusade took place during an economic growth spurt in Oregon, when it was easier to backfill revenue losses to minimize cuts in services. Not so today, when the state and local governments are facing budget shortfalls that will magnify the impact of any tax cuts on services that voters care about – from schools to health care.
Sizemore’s modus operandi was to file multiple measures and proceed to the ballot with the few that polled the best. Von Schlegell and his team are likely to follow suit. But I’d bet that when they do their polling, they’ll find that their tax-cutting initiatives won’t easily pass muster with the voters, while their results-oriented reforms of government will be better received.
So, perhaps they’ll ditch their attempt to roll back taxes and promote the policies that will force state government to do a better job with the resources it has. Even I, who was part of the effort to defeat Sizemore those many years ago, would be fine to see that effort go forward in the years ahead.
See all 11 of John von Schlegell’s petitions
- Initiative Petition 57 would require state agencies to grant or deny permits within 90 days.
- Initiative Petition 58 would mandate independent school audits be posted online.
- Initiative Petition 59 would require judges to appoint public defenders instead of delaying trials or dismissing charges.
- Initiative Petition 60 would establish a 10-year sunset on all state taxes and fees.
- Initiative Petition 61 would automatically add all urban reserves into cities’ urban growth boundaries.
- Initiative Petition 62 would apply federal campaign contribution limits to state and local races.
- Initiative Petition 63 would allow taxpayers to deduct local taxes and fees from their reported income on state taxes.
- Initiative Petition 64 would block judges from releasing people deemed incompetent to participate in their own defense.
- Initiative Petition 65 would ban corporations and unions from donating to political candidates.
- Initiative Petition 66 would prohibit taxes on inherited income and property.
- Initiative Petition 67 would require two-thirds of voters to approve new or increased taxes adopted by ballot measure.
Tim Nesbitt, a former union leader in Oregon, served as an adviser to Democratic Govs. Ted Kulongoski and John Kitzhaber and later helped to design Measure 98 in 2016, which provided extra, targeted funding for Oregon’s high schools. This guest commentary is from news partner Oregon Capital Chronicle, and it may or may not reflect the views of The Corvallis Advocate, or its management, staff, supporters and advertisers.
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