The next time you’re down on your hometown or complain that things have gone horribly awry, you can always rest assured that someone else’s misery is even greater. Such is the case with Winsted, a faded mill town in the Litchfield Hills that is in such deep trouble that some are hoping the state will come in to clean up the mess.

The trouble had been brewing for decades but came to a head in late August when Henry Centrella, the town’s finance director since 1983, was arrested by State Police and charged with embezzling at least $2 million, but perhaps as much as $7 million. Partly as a result of the alleged thievery, the town, formally known as Winchester, is flat broke, has a dismal bond rating, and has virtually nothing in its cash reserves.

Centrella’s tale reads like a made-for-television movie. Police say he had a mistress in Florida to whom he had become engaged. He was looking into buying property in the Sunshine State. When asked by the woman where he got the money to support his extravagant lifestyle, Centrella told her he was an early investor in Google stock and he had sold 88 acres of real estate to Disney. Suspicious about all the cash Centrella carried, the mistress traveled to Centrella’s modest Winsted home, where his wife answered the door.

But the rude awakening that confronted Centrella’s paramour paled in comparison to the seismic activity that rippled through the town when he was eventually taken to Troop L and charged with five counts of first-degree larceny, even as Winsted struggled to pay its bills and the school superintendent said the town’s public schools could close in December for lack of cash.

But elected officials and town taxpayers cannot absolve themselves of any blame in this fiasco. A revolving door of town managers, poor supervision of Centrella, mostly flat budgets to avoid tax increases, and constant bickering between the boards of selectmen and education set the stage for a fiscal calamity only made worse by Centrella’s chicanery.

The town’s history of strife and instability goes way back. Inside the Winsted post office is a mural of men arguing and threatening each other on the street during the administration of Abraham Lincoln. Back-to-back hurricanes in 1955 brought devastating floods to downtown, wiping out retailers, uprooting slums on Main Street, and carrying tenants down the Mad River to their deaths.

Even the good people in the town — and ironically, there are many — struggle to bring order to the chaos and the parsimony. Two and a half years ago, the state Education Department took over the schools in Windham, a hardscrabble town roughly the same size as Winchester. Pushed by the General Assembly, the state took control of the Hartford public schools in 1997. Many of Winsted’s most level-headed residents are hoping the state will do the same to ensure that the schools stay open and the finances are straightened out.

Register Citizen file photo
Deferred maintenance has caused infrastructure to crumble. Some pothole-ridden roads are in such deplorable condition that they will have be rebuilt rather than simply resurfaced. The streets and bridges are in such bad shape and the town’s political situation so unstable that a highly respected public works director resigned in frustration last year to take a similar job in distant New Milford.

Three years ago, a fifth-grade teacher suffered severe burns and shock-related injuries when she turned on the light switch in her classroom in the town’s middle school. An explosion and fireball sent her to a burn center in Bridgeport and necessitated the closing of the school for three days. Literally adding insult to the injury of public servants, a pension program for retired town police officers has been discontinued for lack of funds, resulting in the cancellation of retirement and healthcare benefits to nine former cops. Meanwhile, the school board is under investigation for chronically failing to meet the state’s minimum budget requirement.

Of course, one solution to Winsted’s woes would be improved economic development, with its resulting increase in tax revenues. But there seem to be few viable ideas for the empty mills that dot downtown. Elsewhere, the town is considering applications for a medical marijuana dispensary. Winsted native and former presidential candidate Ralph Nader has agreed to convert a former bank building on Main Street into a museum celebrating tort lawsuits. This has led to the inevitable jokes about what the legendary consumer advocate will do when a patron slips and falls on the steps of his museum.

It seems like the best hope is for the state to swoop in and save the day but officials at the Office of Policy and Management are balking, insisting that the town hasn’t exhausted all of its options yet.

Still, if a recent move to enact a supplemental tax and take out a bank loan doesn’t keep the schools open, OPM may very well reconsider. More than anyone, the state knows that the children in a once-proud town shouldn’t suffer because its adults can’t provide adult leadership.

Contributing op-ed columnist Terry Cowgill blogs at and was an editor and senior writer for The Lakeville Journal Company. Until recently, he was development director at The Gilbert School in Winsted. Follow him on Twitter @terrycowgill.

Contributing op-ed columnist Terry Cowgill lives in Lakeville, is a Substack columnist and is the retired managing editor of The Berkshire Edge in Great Barrington, Mass. Follow him on Twitter @terrycowgill or email him here.

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