Straight up the main staircase in City Hall, it’s hard to miss the second-floor portrait gallery of some of New Haven’s past mayors.
Hard not to miss is another gallery, or rather, a piece of the same one. It overlooks the second level, so you know something’s up there if you chance to look. But the angles don’t let you see much, giving you good reason to think nothing more of it. And even if you do want to investigate, there’s no visible path upward. My route involved a series of closed doors, narrow side stairs and quiet hallways of the kind you wonder whether you’re even allowed to use.
You could say it’s just a hair like the strange and bold path that led Roger Sherman to a place of honor at the head of that upper room, where his mayoral portrait, higher and larger than the rest, presides over its own wall. Sherman is nationally famous for being the only signer of America’s “big four” founding documents: the Articles of Association, wherein the First Continental Congress pledged to boycott British trade; the Declaration of Independence; the mid-war Articles of Confederation; and, finally, the Constitution of the United States. He’s also famous, albeit less so, for being a member of the first class of congressmen in the US House of Representatives; a member of the second class of the US Senate; and the first mayor of New Haven.
His resumé runs much longer than that, though, and the balance is singular in its own right. Born in Newton, MA, in 1721, he grew up farming, as most farmer’s sons did. When his father, William, died in 1741, he was the oldest son still at home, entitling him to a share of the estate. He used that money to secure a loan of about £1,200, which he used to follow his brother to New Milford, CT, in 1743, buying up 250 acres of land to start.
But he didn’t farm his impressive new holdings. Instead, he worked as a shoe cobbler while training to become a land surveyor, an attractive path for someone looking to turn loaned money into real. As Christopher Collier notes in his book Roger Sherman’s Connecticut (1971), it was “a trade of more than moderate respectability and a natural entrée into land speculation.” As a surveyor, Sherman could see value where untrained eyes saw cost—and vice versa. By 1745, not yet 25 years old, he’d proven himself skilled enough that the colony’s General Assembly hired him as the New Haven County surveyor, earning him a nice income between wages and fees.
By 1750, he was writing “almanacks,” to use the spelling of the time, and getting them published. In her book Early American Almanacs (1977), Marion Barber Stowell writes that, “for all but a few American colonists, the almanac was the only secular source of useful information and literary entertainment.” The almanac was “clock, calendar, weatherman, reporter, textbook, preacher, guidebook, atlas, navigational aid, doctor, bulletin board, agricultural advisor and entertainer.” Based on original 1753 and 1761 examples preserved in the New Haven Museum’s Whitney Library, Sherman’s almanacs were indeed those things, offering bits of advice, tracking solar and lunar cycles, predicting weather (even 12 months in advance; “Snow every other Day, if I mistake not,” he somehow predicted for the waning days of December 1761), charting distances between various towns and beginning each new calendar month with a poem. To help sell them, he or his publishers placed ads in New Haven’s—and Connecticut’s—first newspaper, The Connecticut Gazette.
Sherman’s almanacs were published “annually or biannually… from 1750 to 1761,” Collier notes, and during this time he added a flurry of new jobs and titles, increasing his public stature. In 1749, he became a “grand juryman.” In ’50, he became a “list-taker,” assessing property taxes, and started a general store with his brother. In ’52, he was elected to the job of “leather-sealer,” responsible for ensuring that “weights and measures were properly taken,” according to Collier. In ’53, he became one of New Milford’s five town selectmen. In ’54, he became a lawyer, gaining admittance to the Connecticut Bar. In ’55, he was chosen to represent his town as a deputy in the General Assembly and gained the title of “justice of the peace” for Litchfield County, which had recently split from New Haven County.
As much as he had invested into New Milford, he would soon move to a bigger pond. In 1760, he opened a store in New Haven, selling books and luxury items, and the following year, he moved into a house on Chapel Street, on the spot where Union League Cafe and what we now call Sherman’s Alley stand; if the house looked the same then as it did in 1885, when his great-great grandson Roger Sherman Baldwin snapped a photo (also kept in the Whitney Library), it was a colonial with a front stoop leading right onto the sidewalk, with a low fence along the front, a bay window on the side and an extended back end. It sat across from Yale, where Sherman would serve as treasurer from 1765 to ’76 and, according to The Life of Roger Sherman (1896) by Lewis Henry Boutell, he would receive an honorary M.A. in 1768. Earlier, in ’64, he was again named a deputy to the General Assembly—this time representing New Haven. He was then promoted, in 1776, to “assistant,” the title for members of the Assembly’s upper house, which he held for nearly two decades. That same year, Boutell notes, “he was appointed a Judge of the Superior Court, and was annually reappointed to that office for twenty-three years…”
In 1774, with national revolution stirring, Sherman was an obvious choice as one of Connecticut’s delegates to the Continental Congress, where he remained a representative until that body’s replacement in 1781. In ’84, upon New Haven’s incorporation as a city, he became the city’s first mayor. Three years later, as a delegate to the Constitutional Convention, Sherman and Oliver Ellsworth, the other representative from Connecticut, introduced what’s become known as the “Connecticut Compromise,” which satisfied smaller states with equal representation in the US Senate and appeased larger states with proportional representation in the House. In 1789, he served in the House’s first freshman class; in ’91, he moved up to the Senate. All the while, he remained New Haven’s mayor, holding the position until his death in 1793.
Farmer, cobbler, surveyor, investor, almanacker, taxman, merchant, regulator, politician, lawyer, lawman, treasurer, jurist, revolutionary, statesman, founding father… Oh, and did I mention he had 15 children from two wives?
Founding father, indeed.
Written and photographed by Dan Mims. This updated story was originally published on January 30, 2015.
