Can a first-time candidate get a step closer to Vermont’s second-highest office? Will voters in Winooski elect the state’s first transgender lawmaker? And who will fill the exceptionally large shoes of Kitty Toll, the outgoing chair of the House Appropriations Committee?

Although most voters have already mailed in their ballots, there is no shortage of suspense heading into Vermont’s first pandemic primary. (Secretary of State Jim Condos says results should come in Tuesday night, per usual.)

Here are five races VTDigger reporters will be watching closely. 

Democratic lieutenant governor — Though the lieutenant governor’s office carries little power, it can launch political careers, and this year’s Democratic race for Vermont’s second-highest political office will almost certainly have implications well beyond this election. 

Sen. Tim Ashe, D/P-Chittenden, the outgoing leader of the Senate, is hoping to certify himself as a statewide political force, while Molly Gray, an assistant attorney general and first-time political candidate, is already seen as a possible candidate for the next congressional opening (Vermont remains the only state that has never sent a woman to Congress). 

Sen. Debbie Ingram, D-Chittenden, and Brenda Siegel, who ran for governor in 2018, round out the field. 

While Ashe and Gray are seen as the front-runners, the success of Ingram and Siegel in garnering votes — particularly in Chittenden County — could be the deciding factor. 

Democratic gubernatorial Rebecca Holcombe started campaigning months before Lt. Gov. David Zuckerman even decided to run for governor. And she continues to have a strong fundraising lead.

Will it be enough for the former education secretary to overcome one of the state’s most recognizable politicians? 

Without any polling ahead of the primary, it’s almost impossible to guess. But one thing is for sure: whoever wins will have an uphill battle against Gov. Phil Scott, one of the country’s most popular governors, whose response to the coronavirus has an 83% approval rating. 

Chittenden Senate race — This year’s most expensive down-ticket primary is in Chittenden County, where Democratic candidates for state Senate have together raised more than $270,000 so far. 

The two seats vacated by Ashe and Ingram opened the floodgates for candidates vying to take their spot (or knock off the four incumbents). 

Kesha Ram, a former House rep from Burlington, is seen as the front-runner among the new crop of candidates, which also includes David Scherr, an assistant attorney general, Dylan Giambatista, an outgoing House rep for Essex Junction, and Thomas Chittenden, a third-term South Burlington city councilor. 

Sen. Christopher Pearson, P/D-Chittenden, received the least votes in 2018 among the returning candidates. The other three incumbents are Sens. Ginny Lyons, Michael Sirotkin and Phil Baruth

Caledonia-Washington 1 House race — The race for the Caledonia-Washington 1 House seat, being vacated by Rep. Kitty Toll, D-Danville, is perhaps the most competitive legislative primary outside of Chittenden County. 

Henry Pearl, a Danville dairy farmer and Selectboard member, Gwendolyn Hallsmith, executive director of an international community development nonprofit, and Peter Griffin, a Danville-based attorney and former lawyer for the Office of Legislative Council, are all hoping to replace Toll, who chaired the House Appropriations Committee. 

The winner will face off against the Republican candidate for the seat, Bruce Melendy, who is aiming to take back what was, before Toll, a safe Republican district. 

Chittenden 6-2 House race — Can the Progressive Party continue its winning streak in Burlington? Progressives have taken control of the City Council, in large part through young candidates beating incumbent Democrats. 

The Chittenden 6-2 House race offers another test of the Progressive tide. Emma Mulvaney-Stanak, a former Burlington city councilor and chair of the Vermont Progressive Party, has mounted a primary challenge to incumbent Rep. Jean O’Sullivan, D-Burlington.

O’Sullivan has served in the Vermont House for eight years — since she was appointed in 2012 to represent the district, which comprises both the Old and New North End. 

Correction: A previous version of this article said that Thomas Chittenden is a former South Burlington city councilor. He is currently on the city council.

Colin Meyn

VTDigger Managing Editor

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Colin Meyn is VTDigger's managing editor. He spent most of his career in Cambodia, where he was a reporter and editor at English-language newspapers The Cambodia Daily and The Phnom Penh Post, and most...