It’s been two and a half months since Election Day, which means I’m way behind the Political Observer curve in terms of looking ahead to the next election.

Or perhaps the 2028 election, depending on when Gov. Phil Scott decides to retire undefeated. Because until that happens, there won’t be a serious contest for the Democratic nomination — and when it happens, we’re going to see a political stampede the likes of which we haven’t seen since Jim Douglas’ retirement in 2010 touched off a five-way contest in the Dem primary.

If you think it’s Way Too Early^TM for such talk, well, let me tell you, the engines have been revving for some time now. Recent examples: Former Burlington mayor Miro Weinberger’s emergence as the public face of Let’s Build Homes, a nominally bipartisan slash nonpartisan organization promoting the cause described in its name; and the obligatory tongue bath given to Lt. Gov. John Rodgers in the cover story of last week’s Seven Days, which touted the notion that this crusty, ornery Son of the Soil^TM was suddenly transformed into gubernatorial timber by his extremely narrow plurality victory over David Zuckerman. Which I don’t buy, but hey, I’ve been wrong before.

In reality, the race to succeed Scott began at least two years ago and maybe four, when Mike Pieciak left his post in the, ahem, Scott administration to run for treasurer and immediately succeeded his predecessor Beth Pearce as the person most likely to get a standing ovation at party meetings. Pieciak’s been fundraising far beyond his minuscule needs ever since, and the only plausible explanation is that he’s preparing to run for governor as soon as Scott steps aside.

A more pointed signal of Pieciak’s intent could be seen in his November 19 campaign finance report: a $3,000 payment made on November 6 to Silver Strategies, LLC.

When I see an unfamiliar business in a campaign finance filing, my first stop is the Secretary of State’s business name search webpage. There I typed in Silver Strategies, and found that the principal is one Natalie Silver.

Aha, I thought.

Those who follow #vtpoli closely will recognize the name. For those just joining us, Silver is one of the most accomplished political strategists in Vermont over the last decade or so. She has never run for office, but she’s been associated with winner after winner since at least 2016. Silver was TJ Donovan’s political advisor when he ran for attorney general after Bill Sorrell stepped aside (in advance of a likely defenestration by his fellow Democrats), and served as Donovan’s chief of staff until the spring of 2019. Since then she’s worked on Peter Welch’s campaign for Senate and managed Becca Balint’s 2022 run to succeed Welch in Congress — which involved a decisive victory in what began as a closely-contested three-way Democratic primary.

Silver remained as Balint’s political advisor between campaign seasons and then managed her 2024 re-election bid. Shortly after the election, Silver switched horses and signed on as an advisor to Pieciak — a move first signaled by that $3,000 payment to her consultancy.

Silver confirmed her new affiliation with Pieciak, but otherwise offered no comment. Looking at it from the outside, I can see no explanation for the move besides a bid for higher office in Pieciak’s future. I mean, he doesn’t need Silver’s help to beat whatever tomato can the Republicans might put up against him in a future race for treasurer. And why would she forego an alliance with Balint, who’s first in line to be our next U.S. Senator at some point in the not-too-distant future, to go to work for a state treasurer? It makes no sense for either of them unless there’s a gubernatorial bid in Pieciak’s future.

So now let’s spin it forward. If Scott runs for re-election in 2026, then Weinberger can probably have the nomination of he wants it. Other plausible hopefuls would stay out of the way. Weinberger would be the highest-profile gubernatorial candidate fielded by the Dems since Sue Minter in 2016. Which is not to say he’d win because he wouldn’t, but he could raise enough money to fund a decent campaign in a way that past nominees Esther Charlestin, Brenda Siegel, then-Lt. Gov. David Zuckerman and Christine Hallquist could not.

If Scott does bow out in 2026, Weinberger would likely find himself elbowed aside by a pack of mainstream Dems, with Pieciak in pole position. If Scott persists beyond his fifth term, then Pieciak bides his time in the treasurer’s office, where he can launch small but meaningful and plausibly populist initiatives and cement his status as a rising star. But whether it’s 2026 or 2028 or, gack, 2030, there will be plenty of others jostling for position in the mainstream Democratic lane: Weinberger, Senate President Pro Tem Phil Baruth, state Sen. Kesha Ram Hinsdale, Secretary of State Sarah Copeland Hanzas, Attorney General Charity Clark, and former lieutenant governor Molly Gray come to mind. If that kind of field were to emerge, then Zuckerman would have a real chance at winning a Democratic primary with a plurality. It would behoove Pieciak to pre-empt as many of his potential competitors before they assemble at the starting line.

Which means a political operation that begins now, as if it hasn’t been in progress for quite a while. Silver makes for a powerful ally in that as-yet-hypothetical race to succeed Scott, an ally Pieciak will need if he’s going to pre-empt the competition for mainstream Democratic dollars and support, and become Vermont’s next chief executive.