Walking in Prince Mortimer’s Footsteps

Last week Connecticut Public reported how Middletown, Connecticut, renamed a street after Prince Mortimer, a man enslaved in that town before and after the Revolutionary War.

Prince Mortimer Avenue was once a walkway connecting the Irish-born trader Philip Mortimer’s mansion and his ropewalk, where he assigned his bondsman Prince to work as a spinner.

In 2006, Denis R. Caron published a book about the enslaved ropemaker: A Century in Captivity: The Life and Trials of Prince Mortimer, a Connecticut Slave.

More recently, John Mills has delved into Prince Mortimer’s life, sharing his work on his nonprofit website and at Enslaved.org. Mills led the push for memorializing Prince Mortimer, as the Middletown Press reported in 2023.

In a Commonplace review, Watson Dennison complained that Caron’s book about Prince Mortimer actually had very little to say about him, and a lot more about the Connecticut prison system in which he spent the last years of his life after being convicted of attempted murder. Dennison also felt that Caron mistakenly portrayed slavery in Connecticut as “a benign institution,” based on outdated analyses.

Studying the latest scholarship is something an author can control. Having detailed sources isn’t. For example, Caron found that no record of Prince Mortimer’s criminal trial survives. So unfortunately there’s no way to recount, much less assess, the evidence in that case.

The sources we do have can also be shaky. The earliest author to write about Prince Mortimer was Richard H. Phelps, who in 1844 published the first edition of his Newgate of Connecticut. Having grown up near that notorious prison made from the Simsbury copper mine, Phelps seems to have created this book for the edification of tourists.

Apparently Phelps conversed with Prince Mortimer himself before his death in 1834. He said the aged inmate was “supposed to be 110 years old,” having been born in Guinea and kidnapped to America as a child. But of course we don’t have records to corroborate that age.

Phelps also described Prince Mortimer as an a war veteran:

He was a servant to different officers in the Revolutionary War—had been sent on errands by General [George] Washington, and said he had “straddled many a cannon when fired by the Americans at the British troops.”

Again, there’s no other record of such service. (And that’s not a safe way to fire a cannon.)

On the one hand, we want to respect the personal statements of Prince Mortimer, wrenched away from his family and terribly victimized through life. On the other hand, exaggerating one’s age, military service, and proximity to the beloved Washington were common fibs for old men in the early 1800s, white or black. Such claims might be most understandable coming from an old man forced into prison after a lifetime of slave labor who needed all the sympathy he could get. 

The earliest contemporaneous evidence about Prince Mortimer appears to be Philip Mortimer’s will, signed in 1792. That document makes clear that “my Negro Prince” was a valuable asset. While the merchant bequeathed freedom to most of the people he enslaved on his death, he wanted Prince and another man, Peter, to “be kept at spinning” in the ropewalk for the benefit of his niece’s husband, George Starr, for another three years.

It might be a mistake to accept Phelps’s 1844 statements as facts and anchor all other evidence about Prince Mortimer’s life to them. Caron and Mills describe Philip Mortimer sending his enslaved man Prince to war in 1780. Even though that man’s skills would probably have made him more valuable, to both his owner and the American cause, in the ropewalk. And even though he was, in their analysis, in his fifties and in poor health. And even though there’s no record of such an action.

At the same time, there’s solid contemporaneous evidence that Philip Mortimer enslaved Prince Mortimer in Middleton, making him work in the ropewalk. He did walk the path now known as Prince Mortimer Avenue as an enforced laborer.

TOMORROW: The Mortimers of Boston.

Peering into a Prison in 1799

Richard Brunton (1749–1832) came to America to fight for his king as a grenadier in the 38th Regiment. That lasted until 1779, when he deserted.

As Deborah M. Child relates in her biography, Soldier, Engraver, Forger, Brunton struggled to make an honest living in New England with his talent and training as an engraver.

One product he kept coming back to was family registers and other genealogical forms. Another was counterfeit currency.

In 1799 the state of Connecticut sent Brunton to the Old New-Gate Prison in East Granby for forging coins. To pay his accompanying fine, he made art, including a portrait of Gov. Jonathan Trumbull, a seal of the state arms, and a picture of Old New-Gate itself.

That prison, also known as the Simsbury Mines, was notorious as a place where the state held Loyalists underground during the Revolutionary War. However, in 1790 the state took over the property and rebuilt it according to a modern philosophy of criminal punishment, based on locking people up for years doing labor instead of physically punishing or hanging them. Brunton depicted the place he came to know during his two-year sentence. 

The Boston Rare Maps page for this print says:

The view suggests that coopering (barrel making) was a major activity for prisoners, as two figures can be seen at upper right engaged in the task, while another at the bottom seems to be bringing a completed barrel to a shed.

Also visible are what appear to be two African-American figures carrying buckets can be seen in the view; these figures, which are completely blackened, stand out conspicuously from the others in the view. It is documented that enslaved African-Americans worked in the copper mine that had earlier operated in the location of the prison. Whether African-American were also engaged at the prison as well is a question for further research raised by this work.

Although the engraving contains an image of a prisoner receiving the lash, as a state prison Newgate followed a relatively humane approach for the period; a prisoner could be given no more than 10 lashes, and there was a limit on time served there. Participation in labor was required of all prisoners, and in addition to coopering they also engaged in nail making, blacksmithing, wagon and plow manufacture, shoe making, basket weaving and machining.

After being released, Brunton went back to Boston, where he was arrested for counterfeiting again in 1807. He served more years in a Massachusetts state prison and finally lived out his life in Groton.

The copperplate for Brunton’s Old New-Gate image survived until about 1870, when a few more prints were made. Only a handful of copies survive, and it’s impossible to tell whether they came from the initial run or the reprint decades after the artist died.

The example shown above was recently acquired by the John Carter Brown Library in Rhode Island. Other prints are at the Connecticut Historical Society and the Massachusetts Historical Society.

“Capt. Ingersoll was tried by a Court Martial”

In 1766, at the age of thirty-one, Peter Ingersoll opened a tavern and inn in Great Barrington, Massachusetts. (It still exists in greatly expanded form as a bed-and-breakfast called the Wainwright Inn, shown here.) He was from one of the town’s leading families, though not from one of its leading branches.

In 1775, Ingersoll was one of the town’s militia captains. News of the fighting at Lexington and Concord reached Berkshire County on 21 April. Ingersoll and his men assembled, and they marched east five days later. When Massachusetts organized an army for service to the end of the year, Ingersoll and many of the men signed on as part of Col. David Brewer’s regiment.

That regiment ran into problems in the fall. Col. Brewer was tried by court-martial and dismissed on 23 Oct 1775 for insisting that his son, also named David, be ranked and paid as a lieutenant. Such nepotism wasn’t uncommon, but in this case David Brewer, Jr., was back home in Berkshire County while his father was still collecting his pay. So that left the regiment leaderless, and perhaps resentful.

In early December, Capt. Ingersoll was brought up before another court martial—apparently at the regimental level since it’s not mentioned in Gen. George Washington’s general orders. Lt. Gamaliel Whiting of Great Barrington wrote in his diary, transcribed in Charles J. Taylor’s History of Great Barrington: “Dec. 4. Peter Ingersoll try’d by Court Marsh’ll.”

A more detailed account, and a different date, appear in the diary of Pvt. Samuel Bixby:

Dec. 7th, 1775. Thurs: Capt. Ingersoll was tried by a Court Martial for spreading false reports about the Country, tending to defame the General. He was fined £8, and dismissed the service. —

8th. Friday. The same Court fined one man £8.7s., and sentenced him to two years imprisonment in the New Gate Prison in Simsbury [Connecticut], for stealing & deserting; and another man, John Smith, for similar offences, was fined £8, and sentenced to six months at Newgate.

A third diarist, Sgt. Henry Bedinger of Virginia, also recorded court-martial verdicts on 7-9 December, overlapping with Bixby’s account, but not exactly. (He wrote that one man was named John Short.) So it’s not clear whose diary is most reliable. Yet it does seem significant that Bedinger didn’t mention Ingersoll’s case, nor have I found references to it elsewhere. Mike Sheehan was kind enough to look for the captain’s name in Summer Soldiers, James C. Neagles’s listing of more than 3,000 courts-martial in Continental Army records, and it’s not there. So was this proceeding deliberately kept quiet?

Perhaps manuscript records of this proceeding survive in some unexpected archive. They could offer details of what “false reports” Ingersoll spread and how they tended to “defame the General”—namely Washington. Was the tavern-keeper frustrated by the slow pace of the siege? Angry about Brewer’s dismissal? Pessimistic about the Patriot cause?

Whatever the details, Ingersoll went home to Great Barrington, probably in a huff. He went away without filing the paperwork the state would need to pay his men. Since it was already December, and people’s enlistments were up at the end of the year, his early return might not have been that conspicuous. (After all, David Brewer, Jr., had come back much earlier.)

Still, word got around town. The next March, after one of Great Barrington’s militia companies narrowly elected Ingersoll their captain, some men complained. New colonel Mark Hopkins described the problem to the Massachusetts Council:

a large number of the soldiers appear to be very uneasy with the officers elected. Those of the South Company say that Captain Peter Ingersoll was broke last fall by the sentence of a Court-Martial in the Continental Army, and was then declared incapable of sustaining any office in the Continental service.

By July, Ingersoll was out of Hopkins’s regiment and in another, still a captain. But I don’t know how long that lasted. Ingersoll died in 1785.

Local histories—even the one that quoted a neighbor and fellow officer saying he went before a “Court Marsh’ll”—treat Capt. Peter Ingersoll as an admirable contributor to the American cause. They say nothing about how he was cashiered for defaming Gen. Washington.

TOMORROW: Trouble in the Berkshire County militia.

Going to Prison in Connecticut

Anthony Vaver’s Early American Crime offers a traveler’s guide to the Old New-Gate Prison and Coppermine in East Granby, Connecticut.

The site of the prison originally supported one of the first commercial mining operations in the British colonies, before the Connecticut General Assembly decided to convert the mine into Connecticut’s first colonial prison in 1773. Today, a long set of stairs takes you down into the mine shafts, where you are free to wander around without a guide and to discover the eerie cavern once reserved for solitary confinement tucked away in the back of the tunnels.

Outside the mine is a spectacular vista of the Farmington Valley, which must have given some convicts incentive to break out. Despite claims when it first opened that the prison was one of the most secure in the American colonies, its first prisoner escaped only 18 days after his initial incarceration up a 67-foot air shaft, which can still be seen today.

Two years after the prison opened, Connecticut started using it to confine political prisoners. The “Simsbury Mines,” as many people still called the site, became quite notorious among Loyalists. But officials were convinced of its effectiveness. In his 1818 history of Connecticut, the Rev. Benjamin Trumbull (1735-1820) stated that the “prison called Newgate...has been of much greater advantage to the state than all the copper dug out of it.”

I’ve visited the Old New-Gate Prison twice, once while it was open—which was much more interesting. The view and geography are as compelling as the history. The hours on the site’s site are “Fri, Sat & Sun between 10am and 4pm” for walk-in visitors, closed 3 July but open on Independence Day and through October. Vaver recommends visiting on the last Sunday of the month, when a guide offers tours of the Viets Tavern across the road as part of the $5 admission fee.