A Catskill Catalog: Oct. 22, 2008

On August 27, 1845 New York State Governor Silas Wright declared Delaware County “to be in a state of insurrection.” For the previous three weeks, since county Undersheriff Osman Steele was shot and killed on Dingle Hill in the Town of Andes, anti-rent activists had been harassed, chased, and arrested by a vengeful posse of over 300 citizens, impressed, by the sheriff, into law-and-order service from towns with up-rent majorities, towns like Walton, Franklin, and Delhi, the county seat, which was Osman Steele’s hometown.
The posse rode roughshod through down-rent towns: Andes, Middletown, and Roxbury, especially. Years later, John Burroughs would remember being a boy of eight, watching the posse pass his family farm in a hurricane of dust. Anti-renters scattered into hiding, afraid of the murder charge that seemed to threaten anyone who might have been part of the unruly mob of Calico Indians that had showed up the first Thursday in August at the rent-collection auction of the personal property of farmer Moses Earle– his small herd of cows, a few pigs and some tools.
Moses Earle withheld his rent with his eyes open. A deeply religious man in his early 60s, Moses Earle was a tenant-in-perpetuity of Charlotte Verplanck. He also owned, outright, 100 acres contiguous to his leasehold farm. Earle lived with his wife on this small farm a mile up Dingle Hill on the Tremperskill side. His hired girl, Parthena Davis, was a rabid anti-renter. She urged her boss to refuse to pay his rent to make a point, strike a blow for freedom. Earle had the cash to pay. He just wanted to do the right thing.
He decided the right thing was to refuse to pay. Mr. Earle allowed Sheriff Green Moore to conduct a sale rather than submit to the rent. Allies of the landlord, agent John Allen and lawyer Peter Wright, were prepared to bid on Earle’s cows and pigs to recoup Miss Verplanck’s losses. A mob of over 200 disguised anti-rent Calico Indians gathered threateningly to see that such bidding did not occur.
The anti-renters were in violation of the law simply by appearing in public in disguise, an act criminalized by statute designed to combat the terror the Calico Indians had created. For years, these masked men had harassed land agents and law enforcement officers who attempted to enforce the law by collecting legally owed, unpaid, and overdue rents.
Perhaps, the day was lost as soon as the keg was tapped. The combination of anger and alcohol, gunpowder and politics proved explosive.
Osman Steele was one of those guys you either really liked or really didn’t. He was a hotheaded, redheaded, boisterous and confident fellow who had many friends and lots of enemies. He was a notorious opponent of the anti-rent movement, a law-and-order Democrat, a lawman who went out of his way to go after the Calico Indians, cowards, in his view, who hid behind dresses and masks.
Earlier in the year, three Calico Indians from the towns of Middletown and Roxbury - Silas Tompkins, Lewis Knapp, and Anson Burrell - had been sent to Sing Sing Prison after being unmasked in a confrontation with a Steele-led posse.
A fourth, Ezekiel Kelley, was merely fined when he changed his plea from “not guilty” to “guilty.” Anti-renters felt persecuted for the very act of defending their political point of view: that the leftover colonial leaseholds were un-American and invalid.
So tensions were extremely high on the morning of August 7, 1845 when Osman Steele and his sidekick, Constable Erastus Edgarton, arrived in Andes, stopping for a drink with breakfast at The Hunting Tavern on the Main Street. Tavern keeper Ephraim Hunting, an up-rent, law and order man, warned his friend, the undersheriff, not to go up to the Earle farm, that rumor had it the Calico Indians would show up in force, and that Steele, himself, was a marked man.
“Lead can’t penetrate Steele,” the loudmouth is supposed to have said, and he’s supposed to have dumped gunpowder into his drink before he chugged it. Now, every police officer I know is all too aware how easily lead does penetrate, so it sounds a bit made-up-later to me, but when Steele and Edgarton made their way up Dingle Hill Road, there were men in disguise on either side of them, and everybody had had a chance to get a little liquored-up, as some did, and the auction started and stopped and started again, and someone shouted, and someone yelled, and someone shot, and shots fired, bang, bang, bang, bang, and smoke and dust fogged everything, and when the air cleared, Osman Steele, undersheriff of Delaware County, in the course of his official duties, was down, bleeding, shot.
They carried the lawman into Mr. Earle’s house, and laid him on a couch, and men and women on both sides of the conflict tended to him, and he slowly died all that afternoon until eight o’clock that evening when he was dead. Then all hell broke loose.
A posse was formed. Sheriff Moore felt he had to re-establish the rule of law. Vengeance was the goal of Sheriff’s Deputy James Howe, the martyred Steele’s brother-in-law, who spoke for both the family and the law enforcement brotherhood who felt betrayed by the anti-renters, traitors all!
Known anti-renters took to the hills. Some left the mountains for other parts, but many, literally, took to the hills, sleeping in caves and huts up behind their farms, food run to them by supportive family. Villains to some, heroes to others! Men were chased and caught. The governor called out the state militia to aid the posse. Three new log jailhouses were quickly erected in Delhi.
Hundreds were imprisoned. As many as 60 faced criminal charges related to the incident. Two, Edward O’Connor and John Van Steenbergh, were convicted of murder on flimsy evidence and condemned to be hung. Later, their sentences were reduced to life imprisonment, and, in 1846, they were pardoned by newly elected Governor John Young, a Whig elected with strong anti-rent support.
That flashpoint moment on Dingle Hill was the climatic moment of the Anti-Rent War. Over the next several years, the leasehold system withered away, although, surprisingly, a few rents were collected right into the early 20th century.