Two spooks and a grump

The four-year-old George Henry Sharpe, posing with his mother for a portrait, gazes out impassively toward the painter, Kingston artist John Vanderlyn. Guessing from the age of the boy, the painting was probably done in 1832. If that date is correct, the boy’s mother, Helen Hasbrouck Sharpe, would have been about 35. The artist Vanderlyn, then 57, hated doing such portraits, Ulster County commissioner of jurors Paul O’Neill said. Lacking secure patronage, however, Vanderlyn needed the money.

Another portrait by Vanderlyn is of her husband, the wealthy merchant Henry Sharpe. Since Henry died in 1830, that picture must have been painted at an earlier time. The pair of paintings, the one of the father and the other of the mother and child, are now displayed next to each other on the back wall of the Friends of Historic Kingston (FOHK) gallery opposite the Old Dutch Church on Wall Street in Kingston.

Vanderlyn, the first American to have studied neo-classical painting in the best schools in Paris, felt he was destined for better things than portraiture of the wealthier classes of the backwater city in which he had been born. One can well imagine the scene of the grumpy artist grimly capturing the likenesses of the recent widow and her small child. Though no better or worse than any other paintings of this genre, the work exudes a mutual sense of withholding on the part of both subjects and artist. One might surmise that none of the participants really wanted to be there. The work suggests that.


History buff Avery Smith recently discovered the pair of paintings of the Sharpe family at a local estate auction in 2009, bought them, and donated them in June 2106 to the Friends of Historic Kingston. At his talk to the FOHK last Friday, Paul O’Neill thanked Dr. Smith profusely.

“Getting the paintings and researching them was quite an adventure,” said Smith, who lived at 48 Maiden Lane until last year. “I was relentless in my pursuit of a complete provenance,” he said a few days after the FOHK meeting. “I spent many nights doing genealogical work, which I hated.”

Most records suggest that John Vanderlyn was born in a house since destroyed down the same block of Wall Street. His long and mostly unfulfilled life ended in a low-rent hotel on Crown Street a block and a half away from his place of birth. He died a month short of his 77th birthday.


With its bronze statue generally referred to as “Patriotism,” the memorial in the Old Dutch cemetery at the corner of Main and Fair streets in Kingston’s Stockade neighborhood is about the same height as the one honoring governor George Clinton on the Wall Street side of the church’s front door. The plaque on the pedestal below the front of Patriotism reads, “To the undying renown of the rank and file of the 120th New York Volunteers, one of the 300 fighting regiments in the War for the Union. By the colonel of the regiment. 1896.”

The colonel of the regiment was George Henry Sharpe, who lived in a house called “The Orchard,” across from Academy Green two blocks away.

On the back side of the same Connecticut granite pedestal is a list of most of the major battles of the Civil War in which the 120th participated, including Gettysburg. The last item on the list is “Appomattox Courthouse,” where Robert E. Lee signed the terms of surrender ending the bloody conflict. According to O’Neill, who gave an informative talk about Sharpe’s role in the Civil War last Friday at noon to the Friends of Historic Kingston, Sharpe was in the room when Lee signed the surrender documents. O’Neill showed a slide purporting to show a painting of all the attendees in the room at that time. There was Sharpe, one of a dozen people watching Lee sign.

Though Sharpe may have been most proud of his role in the 120th New Yorkers that he organized in Kingston, his role in the war was more prominent than that. He was a spook, an intelligence guy. Vexed by the frustrating lack of intelligence about the size of Lee’s Confederate forces in 1863, general George Hooker, head of the Army of the Potomac, tasked Sharpe to start an intelligence agency within the army. Previous intelligence efforts, including those by the later-famous Allan Pinkerton, had exaggerated Lee’s strength by threefold, one of the reasons that general George McClellan refused to engage his forces with Lee’s.

Photograph of George H. Sharpe, John G. Babcock, an unidentified person and John McEntee at Brandy Station, Virginia, 1863. (Library of Congress)

In January of this year, Jeremiah Horrigan wrote a charming story about Sharpe’s meticulous information-gathering. One of the subordinates assigned to special duty to help assistant provost marshal general Sharpe with intelligence three months before Gettysburg was a young member of the Ulster Guard from Chestnut Street in Kingston named John McEntee, who turned out to be very useful in interviewing prisoners and gathering other military data.

After the second day of slaughter at Gettysburg, McEntee had come to the conclusion that the Confederates were virtually without reserves. General George Meade, newly in command of the Union troops, was inclined to disengage, according to O’Neill, but Sharpe, with the intelligence gleaned by McEntee, persuaded him to keep his troops in position. “We’ll win, it’s just a matter of time,” O’Neill paraphrased Sharpe as telling Meade.

On the third day Pickett’s famous desperate charge up Cemetery Ridge, a moment now acknowledged as “the high tide of the Confederacy,” was rebuffed. Sharpe had been right.


Thanks to O’Neill’s talk and Horrigan’s article, we know of the honors later heaped on Sharpe. But what of McEntee?

We can pick that information up from his Freeman obituary:

“Upon his return from the war as a colonel, McEntee was appointed to a responsible position in the New York custom house. Later he was engaged in business in Boston. He then came to Kingston and engaged in the iron foundry with John Dillon and continued that business until his death. He was alderman from the Fourth Ward In 1881 and served as water commissioner for a number of years. Colonel McEntee was a man of quiet nature, courteous manners, and a…sense of honor. Whatever he did, in war or peace, and in public or private life, was well done. His was a useful and notable career, and the recollection of it, and of his agreeable personality, that of a gentleman of the old school, will long survive him.”

John McEntee, a first cousin to the noted Kingston painter of the Hudson Valley School Jervis McEntee, is buried in a part of the Montrepose Cemetery separate from the plot where most of the members of the McEntee family are interred.


In his presentation September 15, O’Neill showed slides of the interior of the Sharpe home from around 1900. One could see the Vanderlyn painting of George Sharpe and his mother above the mantelpiece in the parlor.

George Sharpe has not been neglected in the intelligence community in which he and John McEntee played a pivotal role at the turning point of the Civil War. As founder of the Bureau of Military Intelligence, he has been given an honored place in the history of the Central Intelligence Agency. O’Neill mentioned that the expertise of one veteran agent includes portraying Sharpe in reenactments. It is not known whether he’s been booked for the dates of the Burning of Kingston scheduled this year for from October 13 to 15, but it sure would be nice to see George Sharpe on the streets of the Stockade once again.

As the tale of these two local spooks and a grumpy painter illustrates, there are few places in the United States whose streets and highways contain such a rich and accessible history as Ulster County does. The potential for authentic historic and cultural tourism is enormous. As always, a balance must be struck. Though not all tourism is ugly, a lot of it certainly is. Rather than display kneejerk support or implacable opposition, we need to strike a sensible balance between protection of irreplaceable resources and the intelligent transformation of unique assets for legitimate and profitable purposes.

There is one comment

  1. James Augustine

    I think the writer of the article has their history a bit confused. In the article, the writer questions whether or not the unnamed veteran CIA agent who portrays Civil War general Sharpe in re-enactments has been booked for the burning of Kingston. The burning of Kingston occurred during the Revolutionary War not the Civil War.

    Also, in an article a week or two ago, the same writer makes a comment that the stockade area is wrongly referred to as “Uptown”. Why is this wrong? I have lived in Kingston my entire life and everyone has always referred to the Stockade district as uptown. Not sure why it is suddenly wrong.

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