Nate is an eleven-year-old boy living in Connecticut under the harsh rule of his uncle, Storch. Orphaned after his mother dies of smallpox and his father perishes at sea, Nate relies on his active imagination and memories of his father's sea stories for comfort. He demonstrates deep loyalty to the enslaved people who serve as his true family, often risking his own safety to protect them.

Paul is an eighteen-year-old soldier in the Connecticut 5th and a former crewmate on Nate's father's ship. Known as a red-haired prankster during his days at sea, he matures into a serious and responsible young man after joining the military. He remains fiercely devoted to Nate and introduces him to the rebel cause.

Storch is a wealthy Loyalist living in Connecticut and Nate's only living blood relative. Despite presenting himself as a proper gentleman to his peers, he is deeply cruel and abusive to his nephew and the people he enslaves. He fully supports the British crown and dismisses the American rebel forces as disorganized traitors.

Eliza is an enslaved woman forced to labor in Storch's household. After Storch sells her husband, Gregory, she focuses entirely on keeping her three-year-old son safe from a similar fate. She provides a nurturing presence for Nate, sitting by his bed during nightmares and serving as his primary maternal figure.

Slash O'Shea is a legendary, fictional pirate who stars in the bedtime stories Nate's father used to tell. Known for losing his hand in an explosion and replacing it with a dagger, Slash steals from the wealthy to help orphans and the poor. His mythic exploits serve as a mental guide for Nate during terrifying situations.

General George Washington is the confident and commanding leader of the American military forces. Dressed impeccably and speaking with a calm but powerful voice, he commands immense respect from his troops. His speeches remind the soldiers of the specific freedoms they are fighting for.

Theo is Eliza's three-year-old son, an imaginative child living under enslavement in Storch's household. He enjoys listening to Nate's pirate stories and playing make-believe. His innocent mistakes place him in significant physical danger due to Storch's unpredictable temper.

Papa is Nate's late father, a ship captain who brought his son along on his voyages after the death of Nate's mother. He filled Nate's childhood with colorful stories of the sea and legendary pirates. His memory provides Nate with a constant source of emotional strength.

Captain Marsh is the leader of the Connecticut 5th, the military unit that includes Paul. He oversees the training and deployment of a diverse group of volunteer soldiers. He initially doubts Nate's utility but eventually accepts him into the camp.

Samuel is the oldest soldier in the Connecticut 5th and the most accurate marksman in the company. He takes an interest in Nate and spends time teaching the boy how to properly handle and fire a musket.

James is the youngest enlisted soldier in the Connecticut 5th. Coming from a wealthy background, he chooses to leave his privileged life behind to join the American fight for independence. He regularly leaves small gifts in Nate's tent.

Martin is a Black soldier in the Connecticut 5th who was recently freed from enslavement so he could fight in the war. He takes on a caretaking role for Nate in the camp while quietly saving money to purchase his wife and daughter's freedom.

Gregory is Eliza's husband and Theo's father. Previously enslaved by Storch, he was sold away a few months prior to the events of the story, leaving his family devastated and vulnerable.

Mr. Marston is a friend of Storch's who shares his Loyalist political views. He supports the British crown and confidently believes the American rebellion will be swiftly crushed by the incoming military forces.