Every time I write about revitalizing Oregon’s economy or restoring Portland’s business climate, someone jumps in with the same line: “the wealthy need to pay their fair share.” It’s become a kind of cultural reflex—simple, emotionally charged, and hard to argue with. But that’s exactly the problem. It feels like the end of the conversation, when it should really be the beginning. Because if we actually want to talk about fairness, about shared responsibility, about what it takes to build a just and vibrant state—then we have to start with a simple question: who’s paying for what?
Oregon’s tax system is one of the most progressive in the country. We don’t have a sales tax. We don’t tax groceries. We fund our government almost entirely through personal income tax—roughly 90% of our General Fund revenue comes from it. That’s not a flaw in the system; that is the system. And in a structure like that, a relatively small number of high-income earners end up carrying most of the load.
According to the Oregon Legislative Revenue Office, the top 1% of income earners in our state—those making roughly $500,000 or more—pay more than 25% of all income taxes. The top 10%, which starts around $150,000 in annual income, cover more than 60% of the state’s entire income tax base. On the other end of the spectrum, the bottom 60% of Oregonians—those making under $50,000 per year—contribute less than 5% of total state income taxes. That’s not a loophole-ridden, unfair system. That’s progressive taxation doing exactly what it’s designed to do: redistribute wealth to fund the common good.
And what do those tax dollars pay for? Everything. Our public schools, from kindergarten to college. The Medicaid expansion that helps hundreds of thousands access basic health care. The social safety nets that keep vulnerable families afloat. Housing initiatives, mental health services, wildfire response, transportation infrastructure—all of it is paid for, in large part, by a relatively small group of high earners and business owners who choose to live and work in this state. That’s not ideology. That’s a ledger.
Which brings us to the risk. Because for all the moral clarity baked into the “fair share” argument, there’s an economic reality that progressives often refuse to engage with: high earners are leaving. Councilor Green’s office recently cited data showing that the majority of people who’ve left Portland in the last five years made over $125,000 per year. These aren’t billionaires with offshore accounts. They’re doctors, engineers, small business owners, creatives, and professionals who—thanks to the rise of remote work—no longer have to live in a high-tax state to keep their jobs. They’re moving to places like Washington, Texas, Nevada, and Florida. States with lower tax burdens. States that feel, frankly, less hostile to success.
When they leave, they don’t just take their families or their spending power. They take tens of thousands of dollars in future tax contributions with them. That’s money that won’t go to schools. That won’t fund addiction recovery programs. That won’t support unhoused populations. That won’t pave roads or fund community colleges or support wildfire prevention. In a state where the vast majority of the General Fund comes from personal income taxes, the departure of high earners is not symbolic—it’s catastrophic.
And here’s the hard truth: we can’t make up the difference without them. Not by raising taxes on the middle class. Not through new fees or surcharges. Not even by closing every corporate loophole imaginable. The math doesn’t work. You cannot lose the top 10% of earners and expect to maintain the programs that serve the other 90%.
This isn’t a defense of the rich. It’s a defense of the programs we claim to care about. I believe in public schools. I believe in affordable housing. I believe in healthcare as a public good. But belief doesn’t balance budgets. Revenue does. And if we want to keep those systems strong, we need to stop pretending that we can vilify high earners and simultaneously rely on them to fund the future. We need to make Oregon a place where success is not resented—but reinvested. Where wealth is welcomed when it’s paired with civic contribution. Where the people who carry the financial weight of the state feel a sense of belonging, not blame.
The irony is that the people most committed to progressive causes—those who fight for public education, climate justice, racial equity, and accessible healthcare—should be the most concerned about losing the tax base that makes those causes achievable. The debate shouldn’t be about how much we can squeeze from high earners before they break. It should be about how we build a system that invites them to stay, contribute, and believe in the shared project of Oregon.
So the next time someone says “the wealthy need to pay their fair share,” I’ll say this: in Oregon, they already are. And if we don’t start treating that contribution as essential—not optional, not disposable, but foundational—we won’t just lose some income. We’ll lose the very programs that fairness was supposed to protect.
If this episode challenged your thinking or helped clarify the real stakes behind Oregon’s tax debate, share it with someone who cares about where we’re headed—whether they live here or not.
Subscribe on Substack, Spotify, or Apple Podcasts to stay connected. And later this week, I’ll be sharing a new letter from True North, my ongoing book project for my kids—and for anyone searching for direction in a noisy world.
Until then, stay thoughtful, stay grounded, and keep building toward a better future—one idea at a time.
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