Tag Archives: Claire Cummings

Lightning Round!

Well, the shower drain of political news is once again backed up, so it’s time to apply some rhetorical Liquid-Plumr and get the system going again. In today’s installment: the VDP at a crossroads, a really stupid lawsuit from a once-reputable publishing house, a complaint about Peter Welch being too good at fundraising, and maybe the worst political cartoon I’ve ever seen. Let the plunging begin!

The Vermont Democratic Party needs to take a look in the mirror. The VDP is once again looking for an executive director. Claire Cummings lasted about one year on the job before offering her resignation under circumstances unknown. As I wrote upon her hiring, “Cummings is the fourth person to hold the job in less than four years — and the fifth, if you count then-party chair Terje Anderson’s unfortunate tenure as interim ED in 2019.” Well, now they’re looking for their fifth in five years, or sixth if you count Anderson.

It’s sad. It’s pathetic. It’s a mess. And now the VDP must hire a new ED in the middle of election season. It needs someone who can hit the ground running with deep knowledge of Vermont and of campaigning. And it desperately needs someone with the guts to confront party elders if need be. I can think of at least one person who fits that descriptor to a tee. No names, because I don’t know where the search is going to go. But i can tell you one thing: If they hire someone from outside the state and/or someone under the age of 25, it’ll mean they’re happy with the status quo. Or, to put it another way, it’ll mean they’re seriously out of touch and full of unwarranted conceit.

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“Looks Like I Picked the Wrong Week to Give Up Sniffing Glue”

You know, I’d hate to be new Vermont Democratic Party Chair Anne Lezak right about now. She took on the job with hopes of ending a long period of internal turmoil at the ought-to-be-prosperous party.

And now, at the beginning of campaign season, she’s dealing with something of a staff exodus. Three party employees have left in recent weeks, leaving only three paid staffers who have a combined tenure of less than one year. Executive Director Claire Cummings came on board in April 2021; Senate Caucus Aide Sally Short was hired in January; and Data Director Madison Thomas joined the staff less than two weeks ago. And speaking of brief tenures, a reminder that Lezak herself just became party chair in December. They’re probably still wearing name tags at the party offices.

The good news, kinda-sorta: This doesn’t seem to be a case of stampeding to the lifeboats or disappearing in shame, as has happened at VDP HQ in the recent past. Rather, all three have left the VDP for better professional opportunities.

Still, their departures are a big setback for the VDP’s campaign machine at a critical time.

The departees: Party finance chair Kate Olney, who’s given notice that she’s taking a job in VTDigger’s fundraising operation; Spencer Dole, who coordinated the Dems’ House campaign for the last two election cycles, is now field director for Lt. Gov. Molly Gray’s Congressional campaign; and party comms chief Asha Carroll, who’s landed a gig with a national nonprofit organization.

“We’re actively looking to fill all three vacancies as quickly as possible to maintain our momentum,” said Cummings.

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The Vermont Democratic Party Continues to Disappoint

In April, when the Vermont Democratic Party hired Claire Cummings as its executive director, many an eyebrow was raised. Not that any of us knew beans about Cummings or could render informed judgment on her qualifications, but we did know two facts: She was very young, and she hadn’t been in Vermont politics very long. Less than a year, in fact.

The track record of parachuted political talent is pretty dismal. You’re far more likely to succeed if you have some experience of Vermont politics and the tangled thickets of the VDP. Still, she got the gig, so maybe she was the best one.

But from what I know now, her hiring seems even more of a stretch. There were at least two finalists for the job with much longer resumes and greater political accomplishments, and with far deeper experience in Vermont and party politics. I did not hear about this from either of them, but from a bunch of folks associated with the party. Who, presumably, are dissatisfied with the hire or they wouldn’t be spilling the beans.

I won’t name the two, because they’ve gotten on with their lives and they didn’t leak the news. But rest assured, their qualifications are rock solid.

I have no knowledge of Cummings’ personal qualities or her performance on the job so far. But the VDP is a dysfunctional snakepit. Or, as an exiting staffer said last winter, the party suffers from a “toxic environment” and “a lack of willingness… to address systemic issues.” It will take a strong hand to whip this organization into shape. And it’s difficult to wield a strong hand when you’re usually the youngest person in the room and you aren’t familiar with the powers and principalities of the party.

If you want a sense of how difficult this job is, Cummings is the fourth person to hold the job since 2018. (The party has also had four chairs since 2017. Not great.)

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New Jockey, Same Ride

Belated best wishes and condolences to Claire Cummings, the new executive director of the Vermont Democratic Party. I trust she has an idea of what she’s walking into, since she worked on the VDP’s 2020 campaign.

You know how it seems like a certain storefront or commercial building seems to be cursed? One business after another opens up, gives it a shot, and then vanishes? Well, that’s the leadership of the Vermont Democratic Party.

Cummings is the fourth person to hold the job in less than four years — and the fifth, if you count then-party chair Terje Anderson’s unfortunate tenure as interim ED in 2019. (The five, in chronological order: Conor Casey, Josh Massey, Terje Anderson, Scott McNeil, and now Cummings.) The VDP has also seen chronic turnover in staff positions. The “senior” staff member is Spencer Dole, who was hired in February 2019.

Party chair has also been a revolving door of late as well. The VDP is on its fourth chair in five years. (Dottie Deans, Faisal Gill, Anderson and current occupant Bruce Olsson.)

The casual observer might expect the VDP to be a powerhouse, given the party’s dominance in state politics. But no. If anything, it’s fat, lazy and stuck in a rut. You hear a lot of talk about energizing the VDP, winning back the governorship, and opening the door to young Democrats and BIPOC Vermonters. But when it comes time to put words into action, it’s pretty much the same ol’, same ol’.

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