Siobhán Brett is the opinion editor at the Maine Trust for Local News.

My car broke down in Rockland early last Monday morning and, after borrowing a hammer from a trusting gas station manager and trying and failing to tap the starter back to life, I joined the tow guy for a snowy hourlong drive to my mechanic in central Maine. 

On the way, the driver told me he grew up in and around Portland. He moved north because costs rose out of his reach. Maine, he said, had gone crazy.

He’s renting in the Midcoast now. It’s quiet where he is, he allowed — did I detect some youthful disappointment? — but it’s scenic. We rolled past the scenery, talking about trying to quit vaping, pickup truck drivers who think they’re unstoppable and the reliable fun of local gossip that somebody in his position gets to triangulate. 

The mechanic — who, like the tow guy, is always busy — reviewed my troubled car despite being up to his eyes; a variety of kindness and pragmatism that’s the preserve of the small independent business.

The car needed some work. The Uber driver who eventually brought me to the Concord Coach told me he desperately needed a change. A veteran from Down East who has worked a number of jobs in and out of Maine, he currently lives in a trailer outside Augusta. He listed off a lot of places he knew to be warmer and cheaper. In a short space of time, I learned that his speech was not the product of late-March anguish or some other expression of impatience for spring.

Do you know how much money Portland wastes on schools and social services, the driver asked me. And it’s not just Portland, he said. He had statistics to hand about how unlivable Maine was compared with other states, about how much the average person was being taxed here. He raged against the reevaluation of property and its effect on cash-poor homeowners, forcing many of them to give up the only asset they have. 

“Maine’s gone crazy,” he said sadly.

***

At work the previous Friday morning, I met on Zoom with a number of Maine men and women we might call “high-net-worth individuals.” They joined the meeting to make a strong case for taxing the rich in Maine. If they get their way, each of them will pay much more in state taxes.

All going well, over time, they believe a state-level commitment to robustly taxing their wealth will alleviate the sting felt by the guys I drove the roads with the following Monday.

One person likened the effect of this increased taxation to little more than a “rounding error” for rich people. For some, stock market gains or losses in the space of one day are higher than taxes paid to the state in one year.

Some of the group were heirs of fortunes or beneficiaries of trusts. Others were, to use another lamentable bit of Fortune 500 jargon, “self-made.” Some had family members who agreed with them, others did not. We talked about silver spoons, shareholding transfers that could be managed essentially tax-free and how cynicism about state government, the commons and the public good was the type of cynicism we simply could not afford today. Charity and philanthropy, we also acknowledged, can only go so far.

The call had come about at the urging of a local research organization and I joined it, squintingly, with that layer of coordination on my mind. As the exchange progressed, I was both relieved and impressed to find members of the (unchaperoned) group personally familiar with one another and roving wherever they pleased, conversationally. It was abundantly clear to me that they had done, and continued to do, their own informal coordination. Some of them told me they have been asking Maine legislators to do this for years.

Our conversation was not confined to income or to the numbered bills before the Legislature in the present session; it veered into property ownership, tourism and more. The need for specificity, nuance and creativity was repeatedly acknowledged.

At some point, one woman said very simply: “$30 million is very different to $30,000.” 

Well, yes. Most of those in attendance needed to hang up after an hour. I stayed on the line with a couple of people who seemed to want to make sure I was going to be able to convert their anger into readers’ anger. Not that the reader would be angry with them, but with a system of state government that seemingly doesn’t know what to do about them and their wealth — or knows and is too fearful to do it.

Before signing off, I sent them a link to the Matt Yglesias blog post about taxing Maine properly that did the rounds last year. “Tax the tourists,” wrote Yglesias, a political and economic columnist for Bloomberg and others. “Maine should make the summer people pay.”

The map illustrating Yglesias’ post shows almost every U.S. state in shades of orange, charting a percentage of houses that are vacation homes of between 1% and 10.2%. Maine features in maroon with 15.6%. Although Yglesias (himself a summer person!) was making a different and more narrow argument for taxation than the “wealthy Mainers” who got on the phone with me are, Maine hasn’t been able to follow that argument, either.

***

That same week, the New York Times’ real estate section covered a very flimsy survey. Brazenly headlined “The Best Small Cities for Big Careers,” the write-up of a “market study” by an online booking platform named Coworking Cafe counted Portland in the top 10 “smaller U.S. metros where job opportunities abound and a higher quality of life awaits.”

Reading directly from the study, I flinched. Portland, it trumpeted, “recorded a remarkable 40% wage increase from 2019 to 2024 and has seen its employment rate rise by 7.1% over the same period. Pair this with accessible housing, solid safety indicators and excellent amenities, and Portland emerges as one of the Northeast’s most livable and well-rounded cities, even with a more modest $82,059 median income.”

Remarkable indeed. “‘Best small cities to live in as a remote, white-collar worker making at least six figures’ doesn’t quite roll off the tongue,” a colleague sniffed.

Although this offers a smaller, softer example of the way Maine has changed in recent years, it tells us something about the stickiness of the place, and of a city like Portland. 

I’ve lived here for five years; the inflated New York City salary I rode into town with, juicing the stats, paid for rent and restaurant outings for two of those years. It’s hard to add to this paragraph without stating the obvious: the demand in Portland for luxury goods, $20 sandwiches and costly accommodations is plain to see.

The demand for Portland itself is plain to see, and the same can be said of Maine. A good portion of the job posting for the role I’m in now was devoted to the quality of life that can be pulled off here.

If Maine could be persuaded about what it has, uniquely, and could begin to believe and appreciate what people who can (really) pay are willing to pay to live here and spend time here — from Martha Stewart to the level-headed individuals I spoke with the week before last — perhaps the state wouldn’t sweat the academic question of “tax flight.” Perhaps we could get real.

According to a 2023 report of the nonpartisan Center on Budget and Policy Priorities, “state income tax increases on wealthy people have not led substantial numbers of them to move to lower-tax states, certainly not enough to erode more than a small fraction of the revenue the tax increases generated.” The report mentions Maine in passing, making note of “growing tastes for an outdoors-oriented lifestyle.” Sure.

There’s a degree of cultural and political insecurity that confines Maine’s debates about taxation to an outdated binary of a) raise taxes and b) don’t touch taxes. 

The staying power of party-line promises, in this spirit, suggests we have no idea that we are trapped in an environment of stark, stark economic inequality; suggests we have no understanding of the difficult, years-old concept of “two Maines.” Today, there must be at least seven Maines. Would that the approach to taxation made any attempt to reflect that. 

In recent weeks, scores of people testified in support of legislative proposals that would raise taxes on the wealthy and the ultra-wealthy in Maine, several of the people who joined me on Zoom that morning among them.

If Maine won’t listen to the frustrated multimillionaires who are telling us that they firmly believe they should be on the hook for more, that they are willing to be on the hook for more, surely we forfeit the right to make up for that lost revenue in less reliable, more disparate and regressive ways.