(Left to Right) Former Rep. Mary Howard (D-Rutland) and former Sen. Cheryl Hooker (D-Rutland) by Glenn Russell/VTDigger; Independent Rutland County Senate candidate Dave Wolk, courtesy photo; Incumbent Republican candidates Sens. Brian Collamore, David Weeks and Terry Williams by Glenn Russell; Mor timer Proctor, courtesy of the Vermont Historical Society. Background photo by Glenn Russell/VTDigger, photo Illustration by Greta Solsaa/VTDigger. This year, the sole Democrat from Rutland County in the Legislature decided to not seek reelection, leaving an uncertain future for Rutland’s Democratic Party.  The race for outgoing Democratic Rep. Mary Howard’s Rutland District-6 seat includes Democrat Chris Siliski and Republican Cindy Laskevich. The Democratic Party couldn’t find anyone to run for all three Senate seats and six out of 16 of the House seats representing parts of the county, said Thomas Fagan, chair of the Rutland County Democrats. In fact, the three incumbent Republican senators on the ballot — Sens. Brian Collamore, David Weeks and Terry Williams — will also appear as Democrats, having won as write-ins in the August primary. They are facing a challenge from Dave Wolk — who served as a Democratic senator for Rutland County from 1988 to 1992 — who entered the race as an independent, after resigning as Rutland County assistant judge. While Rutland County has long been majority Republican, voters previously had more options on their ballot and have backed candidates with varying political identities.  Rutland County voters sent more Republicans than Democrats to the statehouse in the past decade. Republican legislators occupied around two-thirds of the seats, varying slightly year to year. Last session, Republicans occupied all but one of the seats that represent part of Rutland County, some of whom took office as part of a red wave in 2024.   The Senate doubled its Republican members, and Republicans captured 18 seats in the House. This came after Gov. Phil Scott put his political weight behind Republican candidates to break the Democratic supermajority in the Legislature.  Stephanie Jerome — a former state representative who was one of the Rutland County Democrats ousted in the 2024 election cycle — said the Make America Great Again “MAGA” movement influenced the Rutland County electorate in 2024. “I don’t see it as a permanent red wave. I see it as a temporary red wave instigated by national politics,” Jerome said.  Steven Thompson, Rutland County Republican Party chair, said he sees Rutland County Republicans’ role as providing a counterweight to the left wing and holding off any supermajority of Democratic voices in the Legislature in what he attributed to Gov. Scott’s goal of “balance.”  “Our focus in Rutland County is to help get numbers around the rest of the state, maintain what we have here, and then, you know, continue down that path of balance,” Thompson said.  Political powerhouse Rutland County has been a historic Republican stronghold with significant sway over state politics.  “The Republican Party ran Vermont, and Rutland ran the Republican Party,” Vermont historian and Vermont State University Professor Paul Searls said in an interview.  This was due to industrialist Redfield Proctor, who — along with leading the Vermont Marble Company based in Rutland County into prominence in the 1800s — notably founded what came to be known as the “Proctor Wing” of the Republican Party, Searls said.  The Proctor family was a dominant political force in the state for nearly a century, with Republican coalitions on the east and west sides of the state taking turns choosing political leaders through the custom of “Mountain Rule,” which aimed to alternate and balance geographic representation in the state. Mortimer Proctor, Redfield’s grandson, broke the code of Mountain Rule by seeking the lieutenant governor’s office out of turn in 1940, leading to the custom’s death. Ernest Gibson, Jr. defeated Proctor in the 1946 Republican primary, weakening the Republican establishment’s hold. Following the disruption of the political status quo, Searls said the Republican Party fractured between the “old guard” Proctor wing and the more progressive Aiken-Gibson wing, led by George Aiken and Gibson in the mid-20th century. This set the stage for the rise of the previously marginal Democratic Party across Vermont, including in Rutland County, Searls said.  The victory of Phillip Hoff, the first Democratic governor in over a century, in 1962 helped bolster Democratic support, particularly in Rutland City, said Cheryl Hooker, who served as a representative and senator in Rutland on and off between 1992 and 2022. “I think that people felt that it is possible to have Democratic candidates win,” Hooker said. The pendulum Rutland County has been dominated by Republican support, but Hooker said that a majority of her colleagues hailing from Rutland City were Democrats during her first term in office. The pendulum swung against many Democratic politicians who supported civil unions legislation in 2000, she said.  “Everything changed,” Hooker said. “Civil unions caused a huge bifurcation of the population.” Hooker was one of the few survivors of the red wave during the “Take Back Vermont” movement, she said.  Hooker won one of the Rutland County Senate seats in 2018, and there was a packed field of candidates across the political spectrum running for office during the following 2020 election cycle.  Democrats have failed to recapture a seat representing Rutland County in the Senate since Hooker did not seek reelection in 2022. Voters flipped six House seats to Republican “red” in Rutland County in 2024, after incumbent Democratic candidates were ousted or did not seek reelection in those districts.  Rutland County voted for Democratic presidential candidate Kamala Harris in the 2024 election, but President Donald Trump won 13 towns and 42% of the vote in the county.  Robin Chesnut-Tangerman, former representative of the Rutland-Bennington district who served as a Progressive and Democrat, said the Affordable Heat Act, also known as the Clean Heat Standard, was one of the biggest issues that caused political backlash against Democrats in Rutland County during his time in office from 2014 to 2020 and from 2022 to 2024. Strategy and struggles It was a hard sell to recruit new Democratic candidates in Rutland County this time around, Fagan said, due to the time and financial resources necessary to run and serve.  The party focused on recruiting someone to replace the outgoing Democrat in the House, Rep. Mary Howard, given “how important that seat is to hold,” he said. A full slate of Democratic candidates ran for the three Senate seats and lost against Collamore, Weeks and Williams in 2022 and 2024. Collamore has served as a Rutland County senator for 12 years, and Weeks and Williams have served in the role since 2022. Voters in Vermont in general are “very hesitant to turn out incumbents,” Rich Clark, a political science professor at Vermont State University, said.  Candidates in Rutland County have done well when they seize an open seat and rely on “retail politics,” name recognition and community involvement, Clark added. Weeks said it was “shocking” that Democratic candidates did not run for Senate seats this election cycle. He said winning enough write-in votes to qualify for the Democratic nomination reflects that the three senators are a “good team” and serve Rutland County voters on both sides of the aisle well. The candidates needed 50 or more write-in votes to qualify in the primary, according to Bryan Mills, chief of staff to Vermont’s secretary of state. Fagan called it “a strategic move” on the part of the Republican senators to accept both party labels in their race against an independent, but the candidates are not endorsed by the Democratic Party. Rutland County Republican incumbent senators have sought to differentiate themselves from the national political party. Weeks defined himself as a moderate, social liberal who aims to trim and reprioritize state spending.  “We might be Republicans, but we’re not all drinking the national Republican Kool-Aid,” Weeks said of his political identity. Collamore said the incumbents are all “Vermont Republicans … trying to find a balance and commonsense in everything,” and mainly focused on lowering taxes for Vermonters so they “keep more of what they have.” While he too identifies with the moderate moniker, Williams said he is further right compared to his fellow running mates. The three senators typically vote together, but Williams said they have diverged on certain issues. Williams was the sole no vote against an abortion access and protection bill, for instance.  The Republican candidates in Rutland County campaign as a united force, and it may be to Rutland County Democrats’ detriment that their campaign messages are not in sync, Chesnut-Tangerman said.  Fagan called Rutland County “reddish purple” politically and said that the Democratic Party in the county has moderate and left-leaning candidates that are open to dialogue, but each candidate has their own platform. Chairs of both parties in the county said their candidates are focused on affordability and economic development for the region. For his part, Wolk said he aims to be the first “nonpartisan independent” in the Vermont Senate and seeks to differentiate himself by funding his campaign solely with individual contributions and without political action committee or party money. If elected, Wolk said he could vote based on what he thinks constituents need rather than according to party leadership policy directions as an independent. Wolk entered the race because he is concerned with the ”loud voices on the left and the right.”  For her part, Hooker said she has observed that people in the region irked by political labels this election cycle.  “I think that people also are frustrated as far as parties go,” Hooker said. “People are trying to distance themselves from an affiliation with a particular party and vote more on the values that the candidates have.” Read the story on VTDigger here: The last Democratic legislator in Rutland County is leaving office. What could that mean for the county’s political future?. ...read more read less