The outgoing town supervisor hands the incoming one three envelopes. He says, open number one at the first crisis; number two at the next, and number three when the third one happens, as they inevitably do.
At the first crisis a few months later, the new supervisor opens the first envelope. Inside there’s a note that reads, “Blame the previous administration.” He does. Things seem to blow over.
Sooner or later, the second crisis comes about, and he reaches for envelope No. 2. The note inside says, “Form a committee to study the situation.” Wonderful, he thinks, and appoints a committee that immediately begins its work.
The third crisis arises, and it’s bound to be a bad one. He immediately goes for envelope No. 3.
The note inside reads, “Prepare three envelopes.”
So goes one of the oldest jokes on the political spectrum. I must have told it a hundred times over the decades since the joke was on me. But it was a relief when, after my second term as Woodstock town supervisor (1988-1991), I was able to pass the envelopes on to the next guy. (I didn’t really do that, but I must have told him the joke, and he probably rolled his eyes, having heard it many times before.)
And now Woodstock and the other 19 towns in Ulster County and the City of Kingston are toeing up to the mark for the town races, in what are somewhat denigratingly called ‘off-year elections.’
With Ulster County having a definitively left-leaning populace, more than usual emphasis is placed on the June 27 primaries.
Woodstock offers us with a particularly juicy Democratic primary race to use for our example. Incumbent Democratic supervisor Bill McKenna is running for a fifth two-year term, having succeeded to the position upon the passing of Jeremy Wilber. He will be opposed in the June primary by another Democrat, Bennet Ratcliff, currently on the town board and the chair of the town’s Democratic committee.
Heat has arisen during meetings between the two contenders over issues of finance, of permits, about noise, and about the likely general conduct of the individual should he or she hold such a job.
At the same time as we find potential races across Ulster County for towns in primaries and in the November general elections, we hear of a proposal from the Ulster County Supervisors and Mayors Association to dissolve the county legislature and go back to a board of those same supervisors and mayors, the antiquated system by which the county governed itself until 1967.
Proponents of the plan claim that the county legislature is not responsive to the needs of individual towns. Legislature chair Tracey Bartels contends that there is a general misunderstanding of what the legislature actually does.
If town supervisors feel like they haven’t got enough to do with governing a town, so much so that they’d like to take over the jobs the legislature does, they are in my view much mistaken.
If they’ve got that much time to devote to county affairs, then they are probably not working hard enough being the supervisors in their own communities.
Over the years, people have asked for a description of the job of town supervisor. What it boils down to is taking on, essentially, four full-time jobs.
The first is the job as chief executive officer of this multi-million-dollar per year entity. Which means dealing with dozens of employees in multiple departments, whose lives and livelihoods depend on them keeping their jobs. For instance fielding complaints about diverse topics from potholes to environmental disasters like illegal dumping on someone’s property that leaches on to a neighbor’s. Asbestos in the water pipes? Building projects whose costs climb way past the budgeted amounts? Departments seeking to unionize? The list goes on and on.
The help you have? Minimal staff, which used to consist mainly of an invaluable confidential secretary. Town-board members help sometimes, if the board is united. Lawyers have to be paid. Volunteers step forward for positions on various committees and commissions. All require attention.
The second job is chief financial officer of this public enterprise. In my day back in the last century, Woodstock’s town budget ran to around six million dollars annually, but now it’s considerably more.
Most important is the creation of the preliminary budget, usually after you’ve met with department heads individually and heard their desperate pleas for more help and modest raises. The supervisor must consider what equipment is needed for each department, where places to cut can be found, where to stash some cash and how much for emergencies and future capital projects. The town’s bookkeeper helps.
After you have hashed through several iterations of the budget and satisfied your board, you face your constituents in a series of public hearings. Then the town board votes on it.
You’ve got to watch that budget like a hawk for the whole year, because every overrun could mean another fraction of a percent on next year’s documents, and the taxpayers — remember them? — will be extremely unhappy with their tax bills come January.
Further constraining situations include the state’s tax cap for budget increases, usually around two percent.
The third job follows from the town supervisor being the chairman of the local legislature, which consists of the town board. Need a new zoning law? Form a committee, take two years to write it, go through an environmental quality review, get rejected by the county planners, try to win over the populace and your town board. If you’re lucky and skillful, maybe you can get it done.
Did you know that Woodstock has its own version of the State Environmental Quality Review Act (WSEQRA), with triggering thresholds lower than the state’s in order to better fit the size and tastes of the town? That took about a year to make it on to the books.
How about a law regulating short-term rentals? Or one regulating noise levels? Woodstock and other municipalities have their individual laws about storage of vehicles and overnight parking; about conducting games of chance, about water districts and wastewater districts, and a whole host of other topics. Got extra time, town supervisor? Keep an eye on these.
The fourth job may be the most difficult, or may be the most rewarding. As town supervisor, you are the political leader of your community, the visionary who has an idea and is able to articulate where your community is going, what it should look like, feel like. How do we grapple with the need for housing, where does it go? What should we do with the parcels of land the town owns? How do we bring high-speed Internet to neglected corners of the town? How do we preserve our cultural legacies? Clean up the garbage where it’s habitually being dumped?
Also included under this heading is how we communicate with our citizens, how we listen to their ideas and critiques, whether they agree with you or not. How do you get them to understand that you are trying to do the best by them?
I don’t want it to seem like we lurch from misfortune to crisis. There are many satisfactions of accomplishment. And of course, there is lots more to do than these meager tasks. My list is just a smattering survey of the work involved. There’s surely enough to keep you going all the time.
But hopefully, when you think about who you support to lead your community, you can go at it with a bit of understanding of what the job entails.
And maybe, just in case, tell them to prepare three envelopes.
(We honor the late author Richard Ben Cramer by purloining the title of this article from his wonderful book of the same name.)
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