An ongoing illustrative history study
This piece originally posted on 11/01/2026
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In this last entry before the 2026 midterm elections, we're going to look at the life and career of my fellow New Hamp Shire-folk Wentworth Cheswell, Revolutionary War hero and first-ever elected Black public official in the American colonies... and once again, someone you almost certainly haven't heard of.
Born free in 1745 Newmarket, New Hampshire, Cheswell (sometimes spelled Cheswill) was listed in that year's census (yes, there was one) as "white" but considered himself to be "mulatto" as his father was a free-born Black man (himself the son of a formerly enslaved man who purchased his freedom), and his mother was white. Unusual for someone of his status and ancestry in a New England colony, he attended Governor Dummer Academy in nearby Byfield, Massachusetts (the oldest boarding school in New England). According to the school's records, Cheswell was educated in reading, writing, Greek, Latin, arithmetic, horsemanship, and swimming. He returned home to Newmarket to begin a career as a teacher, later purchasing his first piece of land in 1765 and then marrying and fathering thirteen children. He was a member of the Freemasons and even held his own church pew.
Of significance, in 1768 he decided to run for the office of Town Constable... and was elected. Perhaps a quiet accomplishment and not particularly noteworthy outside of Newmarket, but it does mark Cheswell as the first-ever elected Black official in the American colonies. He would successfully run for re-election to this post every year afterwards, up until his death (excluding, for some undocumented reason, the year 1788). Other town offices he held over the years included auditor, assessor, town moderator, and even coroner.
During the Revolutionary years Cheswell took on additional responsibilities as the Town Messenger for the Committee of Safety, a role which permitted him to ride through battle lines, delivering messages and news to and from Exeter. In December of 1774 Cheswell rode (along with another, soon-to-be-famous rider named Paul Revere) to warn Portsmouth of the approach of British warships. He formally enlisted in the Continental Army in April of 1777, and served in a unit under Col. John Langdon. He returned to his beloved Newmarket after the war ended, and resumed teaching, eventually becoming Schoolmaster. Later, as an historian, he published a number of field reports on local archeological findings and relics. And to get a clearer sense of Cheswell's relative wealth and standing, in 1801 he put up $13,000 with four other locals to found the Newmarket Social Library (not properly a public library as would be understood today, but nevertheless the town's first-ever library). In 1805 he was elected to Justice of the Peace, another position he would hold until his death in 1817.
Yet again as an artist I bump up against the annoying reality that... there is no definitive likeness of my subject. Like so many Black figures from the time of the American Revolution, the plain fact is no artist regarded their portrait as something worth capturing. The pictures that typically pop up as the result of an internet image search... are proveably not him. And so as usual I am forced to draw today's trading card entirely from imagination, so: judge that on its own merits.
For a piece that truly does the man justice, look no further than this amazing portrait of Cheswell by my fellow New Hampshire artist Ryan J. Flynn (go check him out), which was formally unveiled this past July and now hangs in the New Hampshire state capitol building in Concord --though predictably, not without some passive-aggressive racist pushback and stalling. A sculpture honoring Cheswell is planned for an unveiling in late 2027, to celebrate Newmarket's 300th anniversary.
Okay, one last check: Are you registered to vote? Find out. I really cannot stress that enough. Make a plan and get to the polls. An awful lot of forces don't want you showing up; there's a reason for that. Don't be intimidated. Folks in a little New Hampshire town reliably turned out for Cheswell; you can do the same.
See you all on the other side of... well, whatever this is.
Next lesson - Watch this space