They spent years trying to make it work. They even moved in together, so to speak, sharing staff and consolidating departments in hopes that it would confirm their compatibility. But some relationships aren't meant to be, and after a messy, century-plus entanglement, the Town of Essex and the Village of Essex Junction are heading toward a split.

The potential breakup of Vermont's second-largest community comes on the heels of two votes this spring in which residents were asked to merge their distinct but overlapping municipalities. Villagers, whose taxes would have dropped, voted overwhelmingly in favor, while town-outside-the-village residents, whose taxes would have increased, voted overwhelmingly against. Both times, the merger failed by fewer than 30 votes. 

Convinced that they will never have a willing partner, most villagers now want not only to call off the marriage but to break up entirely. They have urged their elected officials to begin the process of separating from the town by drafting a charter for a new City of Essex Junction. The move would slam the door on the decades-old goal of a combined Essex and require significant work to disentangle the two municipalities. Even some of the most ardent supporters of the merger are convinced that it's time to move on.

"Separation is really the only thing we in the village can do to be the masters of our own destiny," said Andrew Brown, president of the Essex Junction Board of Trustees. He added that he sees "zero possibility" the village will change its mind. "We're so tired of this."

Essex Junction was incorporated in 1893 as a village within Essex Town by residents of the more densely populated Five Corners area who wanted amenities their more rural neighbors didn't. But as the population of the town-outside-the-village grew in the 20th century, town government began offering duplicate services community-wide. Village residents found themselves paying for redundancies such as two libraries, two recreation departments and two fire departments.

The merger debate predates many of its participants: The concept was first raised in the 1950s, and a handful of votes have taken place since then. Explanations for the rejections have varied, but taxes almost always played a role.

Non-village residents pay municipal taxes only to the town. The 10,600 villagers, who constitute about half of the suburban Chittenden County town's population, pay into both municipalities. Consolidations over the last decade have aimed to more evenly distribute the financial burden. The two municipalities now share administrative staff and highway and stormwater services, while the town picks up the tab for both public works departments. Still, villagers pay $925 more in municipal taxes on average.

"We can't do it anymore," said Elaine Haney, a villager and former chair of the town selectboard who advocated strongly for the merger. "Vermont is so expensive. Chittenden County is so expensive."

The latest merger proposal would have evened out taxes through a phased approach: Non-village residents who owned a $280,000 home would have seen their bills increase an average of $25 a year for each of the next 12 years. The village would have continued to pay some of its unique costs, retiring its own municipal debt, for example, and plowing its sidewalks. The town would have absorbed the rest of the village budget.

On the whole, villagers viewed the merger proposal as a generous compromise. Their counterparts were not so sure.

Town selectboard chair Andy Watts said many non-village residents bristled at the idea of taking ownership of a budget that was created without them. "Why should we pay for things that we never got a chance to vote on?" he said, recalling the criticisms.

Indeed, non-village residents say they were given few good reasons why they should accept the proposal. Amid calls for a "Greater Essex," as one website run by the village and the town was named, many were left wondering: What's in it for me?

"A lot of people felt as though that big question ... wasn't sufficiently answered," said Tracey Delphia, who was elected to the town selectboard in March.

Non-village residents argue that the lack of incentives was emblematic of a larger problem: While the trustees represent villagers, and the selectboard represents the entire town including the village, no one advocates solely for non-villagers. They repeatedly called on the selectboard to appoint a group that could negotiate on their behalf, but the selectboard declined — a decision that some critics say contributed to the merger's failure.

Though some merger supporters concede that villagers had more to gain, they say efforts to explain how non-village residents would also have benefited from the merger were drowned out by unrelenting opposition.

"There's a propaganda machine that exists in our community," said Brown, the village president. "The amount of blatant misinformation just passed out to be truth was incredibly frustrating, because it's so easy for someone to latch on to certain narratives."

Brown refused to name them, but he was likely referring to Irene Wrenner and Ken Signorello, two of the merger proposal's leading critics.

Wrenner and Signorello run a monthly newsletter called the Essex ReTorter, a play on the local newspaper, the Essex Reporter. They frequently attend local meetings and can often be found waging debates on a town-wide community Facebook group, where politically tinged threads can draw hundreds of comments. They also ran an anti-merger political action committee, NoMergerNow, that raised $9,000 ahead of the two votes (A pro-merger PAC, One Essex, raised more than $11,500).

In an interview, Wrenner and Signorello said their priority was to keep officials honest. They said information coming out of the town offices routinely displayed a pro-merger bias, whitewashing potential downsides. "Town hall could not be trusted to be the adults in the room," Wrenner said.

Complicating this battle was the fact that both sides were sometimes technically right. Take, for example, a fight over an informative graphic included in a 48-page merger booklet produced by the town. The graphic sought to help residents understand how their taxes would change under the merger. It included two tables: One showed the "total" tax impact for the owners of a $280,000 home outside the village, noting that their tax bill ultimately would rise by about $330 a year. The other showed how the increase would play out over the 12-year phase-in period, resulting in about $25 in higher taxes each year.

In a January presentation on local access television, Wrenner and Signorello said the graphic misrepresented the tax increase by not clearly explaining how it compounds. They said the more relevant number for non-village residents would be $2,062, since that's how much more the average homeowner would pay during the 12-year period. Their presentation prompted two selectboard members and two village trustees to write a six-page rebuttal titled, "SERIOUS MISINFORMATION ABOUT MERGER."

In the end, neither was wrong: Non-village residents would have paid roughly $2,000 more in taxes on average over the 12-year period, while the total yearly increase would have been about $330. But the net effect of this and so many other tit-for-tat debates, according to selectboard chair Watts, was that many people "just didn't know who to believe."

After the first vote failed on Town Meeting Day, villagers circulated a petition calling for an April revote. But they also pushed for an advisory question asking whether the village should become an independent city should the merger fail again. Village officials say the two items were included on the same ballot to save money. But many non-village residents "felt like they had a gun to their head," Watts said.

"They said it felt like a threat and they weren't going to bow to it," he said.

Villagers, meanwhile, felt like they were the ones being "held hostage," Haney said, which is perhaps why the advisory question passed by nearly a 4-1 margin. The message was clear: Villagers were fed up.

"This was the most generous offer we could come up with," said village trustee George Tyler, reflecting on what he took away from the result. "We have to understand that no means no."

Completing the breakup won't be easy: A series of consolidations have so intertwined the municipalities that it can sometimes be hard to tell where one ends and the other begins. The two currently share a police department, a municipal manager, a clerk, a finance director and an assessor. The recreation departments are colocated at the same building at Maple Street Park.

The true cost of separation won't be known until officials decide whether to continue any of these sharing agreements, according to joint finance director Sarah Macy, who said even rough estimates require her to make an "insane" amount of assumptions. Even so, preliminary figures suggest the toll could be significant — particularly for the town, since the village represents 42 percent of its tax base.

Were the two municipalities to unravel all existing agreements and share costs for the police department — one potential scenario — then the town would need to cut up to $2.7 million in spending to maintain its current tax rate. 

The village, of course, would have its own new costs, especially if it needs to hire new administrative staff; most of the shared positions are currently paid by the town. Still, officials estimate that villagers could pay up to 30 percent less in municipal taxes after separation.

"The town has to prep itself for hurt, financially," said town selectboard member Patrick Murray, who lives in the village and supported the merger.

Given this expectation, some non-village residents appear wary of the split. Speaking at a virtual selectboard meeting last week, Meghan Humphries said she had hoped officials would try again with a different proposal. She said separation would undoubtedly cost more money and make Essex less attractive to prospective residents.

"It just feels like we're dismantling our town and dismantling everything that has made us strong and good and cohesive for a long time," she said.

Others, including Signorello, see separation as the town's best path forward. Even if non-village residents end up with the same tax increase they would have had under the merger, he said, "it will be worth it."

"We won't have to have [villagers] involved in our decisions," he said.

Town and village officials expect to soon begin discussing how a separation might work. But consensus may be hard to find.  

Tyler, the trustee, cautioned that the village should not approach exit negotiations dead set on severing all ties. Noting that separation would ultimately need legislative approval, he said the village should strive to cause the least disruption to both municipalities. But Brown, the village president, seemed less interested in the status quo, saying the town should have very little input on the village's exit plan.

"Separation is not a negotiation," he said.