The reluctant pirate from Ipswich, Captain John Fillmore

John Fillmore and the pirate Captain Phillips
The first-hand account of John Fillmore, Ipswich native, who was forced into service by pirate John Phillips on September 5, 1723.

John Fillmore was born in Ipswich in 1702, the son of mariner John Fillmore Sr. who died at sea in 1711. His widowed mother was Abigail Tilton, whose two brothers Jacob and Daniel famously overcame and killed several Indians who took them hostage after boarding their fishing schooner in 1722. After sailing the ship back to Ipswich, their story was published as a poem titled “Tragick Scene,”in the New England Courant, December 1722, published by Benjamin Franklin’s brother James. Daniel Tilton and his son Daniel Tilton Jr. are believed to have died in a shipwreck in the winter of 1758/1759.

Abigail desperately tried to steer her son toward carpentry, which was the trade of her father Abraham, whose house still stands on Argilla Road. Young John apprenticed in the trade, but upon reaching adulthood he obtained his mother’s reluctant consent and joined the crew of the sloop “Dolphin” under Captain Mark Haskell of Gloucester, whose wife was Abigail’s sister Jemima Tilton. The crew set out on a fishing trip in the spring of 1723.

In August the Dolphin was captured off Newfoundland by the notorious pirate Capt. John Phillips. Fillmore was taken prisoner (only a year after his two uncles’ famous ordeal and escape). After many months he and three other prisoners overcame their captors, seized command and sailed the ship into Boston. The Boston News-Letter, the Boston Gazette, and the New England Courant published sensational accounts of the story and “Captain” John Fillmore became a legend in his own time.

The full story is told below with abbreviated excerpts from Fillmore’s own account of the ordeal in italics.

Narrative of the Singular Sufferings of John Fillmore and Others On Board the Noted Pirate Vessel Commanded by Captain Phillips, With an Account of their Daring Enterprise and Happy Escape from the Tyranny of that desperate Crew, by capturing their Vessel

“From my youth I had an almost irresistible desire for undertaking a voyage to sea, which I resolved at all events to gratify, as soon as I obtained a right to dispose of myself. The propensity was so strong, as to induce me at the age of seventeen, to apply to my mother, and request her liberty to go a voyage to sea. She told me that the sloop, Dolphin under Capt. Haskel, was then in the harbor and if I would go with him she would give her consent.”

Captain John Phillips
Captain John Phillips

“I accordingly shipped on board the sloop, and had a tolerable passage to the fishing ground, but soon after our arrival there, we were surprised by the appearance of a ship which, from external signs, we suspected to be a pirate. We were not by any means prepared to oppose so formidable an enemy. By this boat’s crew we learned that the noted pirate, Captain Phillips, commanded their ship. Having often heard of the cruelties committed by that execrable pirate made us dread to fall into his hands.”

Among the pirates was William White whom John Fillmore had known during his apprenticeship. White suggested to the pirate Phillips that Fillmore could be useful with his services. Capt. Haskell was instructed that if he agreed to surrender Fillmore, the others on the sloop could go free, and Captain Haskell presented Fillmore with the choice:

“I took the matter into serious consideration, and after the most mature deliberation determined to venture myself among them, rather than bring the vengeance of the pirates upon my comrades; I therefore went with them, seemingly content, and the Captain renewing his promise to set me at liberty in two months.”

That promise was broken, and then again three months later when Fillmore asked to be set free, upon which Phillips replied,

Set you at liberty! Damn you! You shall be set at liberty when I’m damned, and not before.'”

After a few months at sea the capture of a ship provided opportunity for a mutiny by some members of the pirate’s crew:

One day we came in sight of a merchantman which Phillips imagining would prove a valuable prize. Phillips ordered one Fern, a daring, resolute fellow of the old pirate crew, to go on board of her, and take command, taking some of the old crew along with him. Soon after night came on, Fern proposed to the pirates with him, that as they were now in possession of a fine vessel, and they could make their escape from the tyranny of Phillips, and set up for themselves. The crew accordingly joined, and they began to execute their plan, but Phillips suspected their design.”

“Phillips sent orders for Fern to come aboard his ship, which he did, and Phillips immediately ran his sword through his body, and then blew his brains out with his pistol, exclaiming, ‘I have sent one of the devils to hell, and where is Fillmore? He shall go next.’ Phillips charged me with contriving to betray him but I concluded a lie was warrantable in that case, and consequently replied, that I knew nothing of any conspiracy either against him or his crew. He had a pistol concealed under his coat, which he presented to my breast, and snapped it, before I had time to make any evasion; but happily for me it misfired. He then swung his sword over my head, damned me, and bid me go about my business, adding, that he only did it to try me.”

The last ship to be captured was the sloop “Squirrel of Annisquam”, commanded by Andrew Haraden. Nine months after his capture, Fillmore, Haraden and the other prisoners plotted to attempt an escape by attacking the crew when they came up on deck after a night of heavy drinking. Three officers, the quartermaster and Captain Phillips were all killed by blows to the head from a broad axe and hammers. Captain Phillips body was thrown overboard after his head was severed which the victors nailed to the main mast. It was stored in a pickling bottle as evidence, and the remainder of the crew was held prisoner.

The band of unwilling pirates steered the ship to Boston from Newfoundland and arrived May 3, 1724, but not without one more unsettling occurrence:

When we came in sight of the castle near Boston, we hoisted our pirates’ colors and fired a gun, as a signal for them to come off to us. At this time some of the pirates were on deck, and one of them asked leave to fire another gun, which being granted, put in the cartridge, and stood directly before the muzzle to ram it down, by which means the cartridge took fire and blew him into pieces; it is supposed he did this purposely, in order to escape the punishment which he knew must be his lot.”

Captain John Phillips forcing alcohol on a prisoner at gunpoint
Captain John Phillips forcing alcohol on a prisoner at gunpoint

On the 12th of May, a special Court of Admiralty was held for the trial of the pirates. The hostages “John Philamore,” Edward Cheesman, John Cobs, Henry Gyles, Charles Joymay, John Bootman, Henry Payne, John Baptis, Peter Taffery, Isaac Lassen, and three negro slaves, Pedro, Francisco, and Pierro were all honorably acquitted. Several members of the crew including William White were convicted of piracy. Three were executed in Boston, and three others were shipped to England where it is said that they were also executed. One pirate’s body was strung up on an island in Boston Harbor “to be a spectacle, and so a warning to others.”

The court awarded “Captain”John Fillmore with the pirate captain’s sword, which passed through generations of the family. Fillmore made his home in Norwich West Farm, Connecticut (now the town of New London) and died in 1777. He married three times, had fourteen surviving children, and is the great-grandfather of the 13th President of the United States, Millard Fillmore.


30 thoughts on “The reluctant pirate from Ipswich, Captain John Fillmore”

  1. He is my 6th great grandfather! This is an awesome story! Loved sharing it with my kids! Thank you for posting this!

  2. John’s my 7 great grandfather I can’t wait to tell my grandfather this story, I know he doesn’t know it

  3. Fascinating!! My 7th great grandparents are Mark Haskell and Jemima Tilton making Abraham Tilton my 8th great grandfather! So John is my 1st cousin 8x removed. Love it!

  4. Very proud he is my 8th great grandfather the father of John Fillmore who came to Canada around 1763 to Nova Scotia.This makes Millard Fillmore my 2nd cousin 6x removed.

  5. the house he built in Sprague Connecticut still stands to this day, as well as the house his stepfather built across the street.

    1. Hello Cousin! I am a direct descendant of Captain Haskell as well! And from some Baileys! I actually live in Ipswich and love to walk the same streets that Captain Haskell once walked as well.

  6. He is my 8th Great Grandfather on my maternal side. I want to come visit the area some day. Would love to walk the paths he did.

  7. I guess Mr. Fillmore has a lot of living descendants , of which I am one as well. He was my 6th Great Grandfather on my Father’s Mother’s side. Millard Fillmore is my 2nd cousin 5 times removed.

    1. Exactly! John had a son John who immigrated to Canada and settled in New Brunswick but many sources don’t even acknowledge this line of the family – of which I am a direct descendant. It’s astounding to think that for everyone commenting, we are probably all related!

  8. I am related to Millard Fillmore as well. My name at birth was Fillmore until it was changed while i was little.

  9. I am the 9th descendant of John, a direct line. It is so cool to find all this info as well as cousins!

    1. I am also a direct descendant to John
      Fillmore. Found this out by ancestry
      Search. Had no idea. I’m sure there are many of us. I would love to see Capt. Phillips sword.

      1. Same Here, through My second Great- Grandmother. I hope the rightfull Owners can see it in their hearts to share it.

  10. We are also related……Hello Cousin, from California
    I have DNA relations too some of the Fillmore descendants, in New Brunswick, that is where Our Grandfather was Captured.

  11. Captain John Fillmore is my 7th great-grandfather, via his daughter, Deliverance (Dillie), who m. Benjamin Haskin.

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