Jolley Allen was a nervous man by March 16, 1776. A Boston merchant who arrived from England in 1755, Allen was a Loyalist through and through.
He had sold, among other things, some of the tea that so infuriated his new countrymen and prompted the Boston Tea Party. And he had been threatened with tarring and feathering for it.
So while he hadn’t accumulated a lot of friends, his connections had allowed him to prosper in the colonies, and he amassed a tidy estate. If you think the idea of losing it all would infuriate him, you’d be right. That’s why he planned to leave Boston behind for a return to England.
Siege of Boston
By March 16, 1776, the standoff between the British and Rebel forces in Boston was as tense as it would get. The rebels under the direction of George Washington had the city under siege. The colonists had fortified Dorchester Heights with cannon, but they were outnumbered by the 10,000 British soldiers who held the city of Boston.
The British, led by General William Howe, faced their own dilemma. They had won the Battle of Bunker Hill, but with enormous casualties. One more such pyrrhic victory and the British might well lose the whole war.
With fresh cannon brought by Henry Knox now looking down on the British from Dorchester, there was no sane alternative for Howe but to retreat by sea. The British, however, needed to provide cover to the Loyalist families that had supported them through their 11-month siege in Boston. They needed an orderly escape.
The colonists, meanwhile, wanted the British to leave without burning Boston. With an informal agreement in place that the British would not burn the town in exchange for the colonials not attacking the British ships as they departed, the standoff dragged on for nearly two weeks. During that time, Loyalists tried to load their ships for departure and the colonists waited.
By March 16, several minor skirmishes had occurred and Howe was convinced Washington was losing patience. And so he ordered the evacuation of Boston the following day, March 17. Jolley Allen was ready to go. His plan was to be on board a ship and simply fall in line and follow the British wherever they went.
On March 11, Jolley Allen had procured the services of a private sloop, Sally, to transport him to England. The ship would be piloted by a 20-year veteran sea captain, Robert Campbell. He spent the next several days procuring introductions and letters of recommendation to assist him in his transition. He also loaded the contents of his two warehouses on to the ship, along with his personal belongings. His furniture alone he valued at more than 1,000 pounds.
By March 14, Jolley, his wife and their seven children had boarded the ship. As more than 100 British ships began leaving on March 17, however, Robert Campbell’s ineptitude became clear. Over the next 24 hours, Campbell managed to collide with two other fleeing British ships, nearly capsize Sally and finally run it aground while the British ships sailed away for Nova Scotia.
It was then that Allen learned Campbell had never been to sea, and knew nothing about sailing. Before long, 20 other passengers from the lower decks joined him in his cabin. Could they join the Allens in their stateroom, the others asked, so that they might all die together?
Allen was flabbergasted to learn that a plank had given way and the ship was filling with water. The captain seemed unable to offer any suggestions. The passengers and crew managed to anchor the ship near Provincetown. When he got to shore in Provincetown it became obvious that Jolley was part of the evacuation, and he was arrested.
Initially some townsfolk offered to secure his belongings, for a sizeable fee. But a friendly stranger clued Allen in that they had already started ransacking his things. By the time he returned to retrieve them, they disappeared.
Allen had to go before the General Court to plead his case. On his way from Provincetown, he passed through Boston and stopped at his old house. His barber had taken it over, but he let him rent a room for two nights.
What little remained of Allen’s belongings disappeared for good when he placed them in the safekeeping of two Boston town fathers.
Finally, in February of 1777, Allen made good his escape and fled to London, where he pleaded his case for compensation, published in “Account of the Sufferings and Losses of Jolley Allen, a Native of London.” Whether he exaggerates or not is unclear, as we only have his side of things recorded.
This story was updated in 2021.