the promise & peril of Gavin Newsom

JMart is right: You have to Admit It. Gavin Newsom Is the 2028 Front-runner.

It’s not even close, really. Prediction markets give him a 37% chance of winning the nomination; nobody else tops 10%. 

It’s a remarkable turnaround from this spring, when seemingly everyone was penning his political obituary. Again.

I could – and eventually may – write 50,000 words about this gritty yet impeccably quaffed, grizzled yet impossibly youthful enigma of a man. (Enigmas never age, have you noticed that?) 

But for now, I offer you a tale of two ballot initiatives that capture the promise and peril of Gavin Newsom.

As I was poring through exit polling from this month’s elections, one little-noticed data point from California jumped out at me:

92% of voters said congressional districts should generally be drawn by non-partisan commissions as opposed to the ruling party, even as they approved Gavin Newsom’s Prop 50 – an initiative to scrap the state’s independent redistricting commission and replace their non-partisan maps with a 48-4 Dem one – by a 30-point margin.

The point here isn’t to shame CA voters as stupid or hypocritical; quite the opposite. The point is that they clearly understood the unique circumstances. And that’s a testament to Newsom, who had the strategic foresight, the political adroitness, and – as my JV basketball coach used to say – the big, brass cojones to take on this high-stakes fight, and win it convincingly.

When Newsom was first floating his plan, internal polling showed just 38% of voters backed it. Moreover, ballot initiatives tend to begin at their high-water mark and bleed support over time; CA data substantiates that pattern; and issue polling significantly over-estimates support for ballot measures. 

There were also myriad legal, logistical, and political hurdles. In short order, he would have to overcome intraparty opposition, raise $100M dollars, draw new maps, get the legislature’s signoff, finesse the ballot language, and win over a skeptical electorate. Plenty of Newsom allies warned about the pitfalls of this gambit.

But to doubt Gavin seems only to encourage him. Basically, when he was a young boy struggling to overcome dyslexia, his exasperated mother told him it was okay to just be average, and he’s spent the subsequent half-century endeavoring to prove her – and everyone else – wrong.

And I’m not saying I’m happy about that foundational trauma, but frankly, Democrats could use a little more of this ‘fuck you, watch me’ energy.

Because we’ve become so data-addicted and risk-averse, we rarely take up a fight unless public opinion is already squarely on our side. But if you’re a political leader, sometimes you gotta – ya know – lead. 

We’ve developed a two-way trust deficit with voters; it’s not just that they’ve lost faith in us, but also that we’ve lost faith in them.

We should give people more credit. It is still possible to level with folks – to make cases that aren’t as tidy & high-testing as “lower costs” – and convince them your fight is righteous, and in their interest.

In a meek party, Gavin Newsom is not afraid to try things; he believes in people, and his ability to lead them, if nothing else. And Prop 50 was a hell of a proof point.

Even as he basks in the glory of his Prop 50 triumph, another CA ballot initiative looms over Gavin Newsom, and this one foretells a more fraught character arc for the frontrunner. (Though as noted above, he does have a knack for rewriting his own story.)

The powerful SEIU-UHW union has been gathering signatures for a proposal to levy a one-time, 5% tax on the total wealth of the state’s ~200 billionaires, and use the estimated $100 billion windfall to offset the Big Beautiful Bill’s steep Medicaid cuts.

Through a spokesman, Newsom – a staunch opponent of hiking taxes on wealthy Californians – ripped the measure as “yet another attempt to grab money for special purposes.” And two long-time Newsom advisors are helming a new PAC in partnership with “business and tech leaders” to defeat the initiative.

One can make a legitimate argument that this specific wealth tax is, as Gov. Gav’s office called it, “bad public policy” – the Q&A on why threatening to seize 5% of SF billionaires’ fortunes won’t just chase them and their tax dollars to Austin leaves something to be desired…

Regardless, the optics are rough; set against the rising tide of economic populism taking hold, this particular showdown could prove uniquely damaging to the debonair governor – a megamillionaire winery owner who looks like he was born in one.

But more broadly, it’s a reminder that while Gavin may have united the base behind his brass-knuckled Trump-fighting in 2025, the 2027 terrain will be far less forgiving; the slick pragmatist’s honeymoon with the left seems likely to end in a Guilfoylean divorce – messy, intense, and regularly featured on Fox News.

Fair or not, he will be pilloried once again for his perceived lack of candor and conviction; tagged anew as a nakedly ambitious, central casting politician – and in a moment that demands working class grit and authenticity, no less.

The truth about Gavin Newsom, as always, is far more complicated than the caricatures. But will anyone believe him?

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