The Rutland Herald went to press around 2 a.m., on Nov. 7, 1984, with a headline deeming Vermont’s gubernatorial race “A Draw” before switching it around 4 a.m. to report Madeleine Kunin’s victory. Photo by Kevin O’Connor/VTDigger Seen all the stories about the Vermont Republican gover nor facing a headline-grabbing challenge from an upstart Democrat? Former Gov. Jim Douglas has — although he’s not talking about this fall’s contest between incumbent Phil Scott and challenger Amanda Janoo. Instead, the 75-year-old retiree is referring to his own 2004 reelection bid against then-Burlington Mayor Peter Clavelle. “Was I concerned about the horse-race coverage?” Douglas recalled in a recent interview. “Yeah. It’s hard to ignore completely. But if I were obsessing over every story and every poll and every pundit commentary, I’d be distracted from the job to which people had elected me.” Vermonters haven’t witnessed a close gubernatorial contest for 10 years — specifically, when Scott won his current post with 52.9% of the vote against Democrat Sue Minter in 2016. Since then, the Republican has increased his margin to 55.2% against Christine Hallquist in 2018, 68.5% against David Zuckerman in 2020, 71% against Brenda Siegel in 2022 and 73.4% against Esther Charlestin in 2024. That momentum could shift Tuesday, when Scott faces Janoo, who the American Prospect reports “is running the most credible Democratic campaign for governor of Vermont in a decade.” If the race is a nail-biter, the Republican will be in good company: All four of his living predecessors — Madeleine Kunin, Howard Dean, Douglas and Peter Shumlin — can each tell tales of their own cliffhangers. The Caledonian-Record of Aug. 14, 1946, reports World War II hero Ernest Gibson besting Vermont Gov. Mortimer Proctor in that year’s Republican primary. Photo by Kevin O’Connor/VTDigger Kunin: ‘Whisker-close’ Only two Vermont governors have lost a race for reelection: Mortimer Proctor, unseated in the 1946 Republican primary by his successor, World War II hero Ernest Gibson; and F. Ray Keyser, a fellow GOP incumbent who was upset in 1962 by Philip Hoff, the first modern-day Democrat to win the state post. Squeaker votes have been far more common. Kunin made history in 1984 with her election as Vermont’s first and so far only female governor. But the now 93-year-old Democrat had to wait until the morning after the polls closed to learn of her razor-thin victory. Kunin, a former state legislator and lieutenant governor, and her Republican opponent, then-state Attorney General John Easton, campaigned neck and neck all fall. The late Saint Michael’s College professor Vincent Naramore, considered “the father of Vermont polling,” released what he called a “whisker-close” survey that October that showed Kunin at 43.8% and Easton at 43.2%.  On Election Day, newspapers told the same story. The Burlington Free Press carried the headline “Too Close to Call,” while the Rutland Herald bannered the question “Who Will It Be?” At 8:35 p.m., the first round of results found Kunin leading Easton, 54% to 45%. By 9:40 p.m., Kunin’s margin had shrunk to 50% to 49%. By 10:30 p.m., she was ahead by a single vote. “The larger Democratic towns had given me a substantial early margin,” Kunin recalled in her 1994 autobiography “Living a Political Life.” “But when the rural towns started dribbling their votes in, my advantage began to erode.” At 2 a.m., with results continuing to trickle, the Herald printed a front page with the headline “A Draw.”  At 3 a.m., Kunin announced she was going to bed. Around 4 a.m., the Herald stopped the press to swap “A Draw” for “Kunin” — news her opponent confirmed when he conceded the race at noon. The final results: Kunin 116,938 (or 50%), Easton 113,264 (48.4%) — a difference of 3,674 votes. The Rutland Herald of Nov. 8, 2000, reports that year’s presidential and gubernatorial results with the headlines “Cliffhanger” at 1 a.m., “It’s Bush, Dean,” at 2:15 a.m. and “Bush? Dean!” at 3:30 a.m. Photo by Kevin O’Connor/VTDigger Dean: ‘Quite an uproar’ Kunin won two more terms before giving way to Republican Richard Snelling, who returned to the governorship in 1991 after serving from 1977 to 1985, only to die in office from cardiac arrest seven months later. Enter Dean, who was juggling jobs as a physician and part-time lieutenant governor when he took over for Snelling. The now 77-year-old Democrat easily won election in 1992 (74.8%), 1994 (68.7%) and 1996 (70.5%) before besting Republican state Rep. Ruth Dwyer by a closer 55.7% to 41.2% margin in 1998. Then in 1999, the Vermont Supreme Court ruled that same-sex couples had the legal right to marriage benefits, spurring Dean to sign a first-in-the-nation law establishing civil unions in 2000. The separate-but-equal compromise angered both voters who saw the differentiation as discriminatory (the state would move to marriage for all in 2009) and those who opposed any deal. “It was quite an uproar,” recalled Dean, who wore a bulletproof vest on the campaign trail. “There were pretty hostile groups that would harass us, and we were getting death threats from all over the country.” Dean went on to win 50.4% of the vote in a race that rematched him with Dwyer (who received 38%) and added Progressive candidate Anthony Pollina (who received 9.6%). But Dean’s victory wasn’t the biggest news of the night. The Herald had to stop the press and switch its headline twice to keep up with the ever-evolving presidential race between Republican George W. Bush and Democrat Al Gore. “Cliffhanger,” the front page read at 1 a.m. “It’s Bush, Dean,” it read at 2:15 a.m. “Bush? Dean!” it read at 3:30 a.m. — a question that lingered until the U.S. Supreme Court ruled in the GOP candidate’s favor a month later. The Burlington Free Press of Nov. 6, 2002, reports Jim Douglas’ first win as governor. Photo by Kevin O’Connor/VTDigger Douglas: ‘Could go either way’ As Dean prepared to leave office in 2002 to run for president, Douglas launched a bid to replace him. The Republican was 21 when he won election to the Vermont House in 1972, then served as secretary of state from 1981 to 1993 and state treasurer starting in 1995. He was in the latter post when he ran in a three-way-gubernatorial race against Democrat Doug Racine, then lieutenant governor, and independent Cornelius “Con” Hogan, former head of the Agency of Human Services. The Sunday before the 2002 election, Douglas picked up the Burlington Free Press — then the state’s largest newspaper — to see a banner headline summing up its exclusive poll: “Racine takes 10-point lead.” “I got on the phone with my pollster,” the Republican recalled, “and he said, ‘I don’t believe it. I think this is dead even. Could go either way.’ I had to get the message out to as many of my supporters as I could that we’re going to keep working as hard as we possibly can in the final 48 hours, and we did.” Two days later, Douglas topped the tally with 44.9% of the vote, followed by Racine at 42.4% and Hogan at 9.7%. In response, his Democratic challenger quickly conceded and asked the Legislature to confirm the results (under a state provision, lawmakers have the final say on races won by less than 50% of all ballots). Douglas was grateful to his opponent. He was less forgiving of the press and the last-minute poll, which its creator blamed on surveying voters on Halloween, “a night when fewer Republicans might have been home.” “After this,” Douglas wrote in his 2014 autobiography “The Vermont Way,” “I became increasingly skeptical of those in the media who never left their urban offices, but made prognostications as if they knew what they were talking about.”  The Burlington Free Press of Nov. 6, 2014, reports Gov. Peter Shumlin’s close reelection. Photo by Kevin O’Connor/VTDigger Shumlin: ‘You have moments’ Douglas was reelected three times before Shumlin succeeded him in 2010. The now 70-year-old Democrat won a close first race against then-Republican Lt. Gov. Brian Dubie by 4,331 votes. But that was a seeming landslide compared to Shumlin’s bid for his third and final term in 2014. His Republican opponent, Pomfret travel agent Scott Milne, was summed up in one press profile as a “reluctant candidate” who, breakfasting on oatmeal and dry wheat toast at Berlin’s Wayside Restaurant, “managed to spend an hour inside the crowded diner a month before Election Day without introducing himself to a single voter.” Nonetheless, Shumlin reaped only 2,434 more votes than Milne on election night. The 46.5% to 45.2% margin sent the race to the Legislature, which didn’t confirm the results until January. Politico blamed the incumbent’s numbers on “stagnant middle-class wages and high property taxes,” technical problems during the rollout of Vermont Health Connect and the candidate’s out-of-state travel as chair of the Democratic Governors Association.  Shumlin had a different take. “Nobody is very happy with incumbents,” he said in 2015. “I understood if I put forth a really aggressive agenda on all fronts, it wasn’t going to be a ticker-tape parade.” Mowing the fields around his Putney home last week, Shumlin said the campaign trail was equally cutting. “You have moments when it gets personal and less civil where you go, ‘I really want to do this job, but is this really worth it?’” he said in an interview. “That stuff really eats at you. But I loved being governor — in my view, it’s the best job in the world — so I don’t regret a minute of it.” Read the story on VTDigger here: Will Vermont history repeat itself with another November nail-biter?. ...read more read less