Lieutenant Caleb Brewster (born September 12, 1747) is an officer for the Continental Army and a member of the Culper Ring. Along with his childhood friends, Abraham Woodhull, Major Benjamin Tallmadge and Anna Strong, Caleb helps to complete spy missions for the Continental Army and General George Washington.
Biography[]
Early life[]
In his youth, Caleb made friends with Abraham Woodhull and Benjamin Tallmadge. The three would look out for each other and do many things together, including escorting Abe to secretly gain a kiss from Anna Strong.
He later became a whaler, going his separate ways from Abe, Ben and Anna.
American Revolutionary War[]
Caleb eventually enlisted in the Continental Army and by the autumn of 1776, he was a Lieutenant.
Ben and Caleb arrived at the Continental outpost in Connecticut to rescue Hewlett, only to discover the outpost been ambushed. Ben discoverd a grave marked with Hewlett’s name, as well as Washington’s letter of pardon for Hewlett. Refusing to give up on Abe, Caleb vowed to personally rescue him from prison.
Caleb and Ben returned to Morristown, New Jersey, where they went back inside Sackett’s former workshop. Caleb showed Ben one of the contraptions Sackett left behind, a one-man submersible craft named the Turtle and revealed his plan to use it to sneak into New York via the harbor.
Caleb began his harrowing underwater journey in the Turtle. He surfaced near a dock in New York Harbor, where he was immediately seen and apprehended by some Redcoats. As the soldiers began to question him, Caleb quietly triggered the Turtle’s mine cask.
As the Redcoats held Caleb at gunpoint, the Turtle’s cask mine exploded. In the ensuing commotion, Caleb shot his captors and escaped. Later, he stole a Redcoat uniform, cleaned up, and shaved off his beard.
Inspector Yates, the warden from Abe’s sugar house prison, brought Abe to his office and handed him over to a Caleb, posing as a Redcoat officer. Caleb told Abe that he’d come to rescue him and updated him on the Hewlett situation. Abe refused to leave, saying Washington’s letter of pardon for Hewlett meant he must still believe in the Culper Ring. Thinking of Robert Townsend, Abe reasoned that Washington would be even more in need of a spy in New York now that the British were relocating their headquarters there. He asked Caleb to visit Townsend and show him how to use the invisible ink.
Aftermath of Arnold's treason and capture[]
Later, after André's hanging, Caleb rushed to Abe’s farm in Setauket to bring the Woodhulls to safety, in light of recent espionage arrests that Arnold had made. Abe, seemingly oblivious that he was in any danger, calmly invited Caleb to lunch.
At Whitehall, Abe assured Caleb that Arnold knew nothing about the Culper Ring. He informed Caleb that Wakefield was stockpiling hay to fuel the army through winter. Caleb asked Abe to delay the hay shipment by one day so that he could return with men to burn the hay. Mary suggested they throw a party on the eve of the shipment and ply the British officers with alcohol to slow them down the next day.
Ben and Caleb later request permission from General Washington to lead a mission to destroy the British hay supply in Setauket. Initially, Washington questiond Ben’s methods, presumably due to resentment over Ben not immediately divulging the receipt of a letter that Arnold’s had written him. But, after Ben stood firm in his commitment to Washington, the General approved the mission.
In camp, Ben, Anna and Caleb planned their attack on Wakefield’s garrison. As Ben and Anna quibbled over a tactical detail, Caleb joked that they fought like lovers. Anna pointed out that everyone in camp believed that she and Ben were lovers and suggested that they use the gossip as cover for their frequent meetings.
The next day, Ben and Caleb arrived outside Wakefield’s fort with their men. Meanwhile, Richard oversaw a meeting between Wakefield, his officers, and the farmers. Ben’s team stormed the garrison, which was poorly defended in the absence of Wakefield and his soldiers. They then burned the hay.
Arnold later discoverd Peggy reading André’s journals in his office. Peggy quickly explained that her curiosity was piqued by Philomena Cheer’s arrest. She pointed out that André was pursuing a spy ring and wondered if a lady named “355” was Philomena. Arnold glanced at André’s journal and noticed a code for a “whaleboat courier.” He recalled that Caleb, a friend of Ben's, operated a whaleboat and deduced that Caleb was the courier for the ring.
Caleb later rowed his boat to the Connecticut coast to trade some goods with his contact, Robbie. British soldiers ambushed Caleb and knocked him unconscious. In return for Robbie’s cooperation with Caleb’s capture, the soldiers released Robbie’s brother, Mr. Betters, whom they held captive. Mr. Betters later informed Washington and Ben of Caleb’s abduction.
Arnold’s men later brought Caleb in for interrogation at Bridewell Prison. A Ranger soon informed Simcoe that Arnold had captured Caleb. Simcoe visited Arnold and informed him that he, too, had been on the hunt for a spy ring on Long Island. He asked to sit in on Arnold’s interrogation of Caleb.
Simcoe waited in the hall as Arnold interrogated Caleb. Caleb pointed out that Arnold couldn't hang him without a confession. He proceeded to mock Arnold for being a turncoat. Arnold stormed out and told Simcoe, “He’s all yours.” Simcoe walked in and punched Caleb.
Simcoe tortured Caleb and referred to Caleb’s “master” as Robert Rogers. Simcoe’s suggestion that Rogers was Samuel Culper, inadvertently lead Simcoe to realize that Rogers was not Culper. Simcoe quickly deduced that Abe was Culper and ordered Caleb to confess. Caleb refused. Simcoe drew his sword and told Caleb that he accepted the challenge.
- "Now, you know who I am. And I know who you are."
"All I know is I'm looking at a dead man."
"If you think your friends will come for you, they won't."
"Oh, it don't matter. I know they'll kill you, and that's as good as me doing it." - ―John Graves Simcoe and Caleb Brewster.
Simcoe continued to torture Caleb and asked him to sign a confession. Caleb spat in his face. Simcoe cut Caleb with his sword and slathered salt on the wound. Simcoe revealed he was born and raised in India and watched his father thrown into the “Black Hole of Calcutta” where he died, and now he taught “mercy is a weakness” to colonists across the country. When Caleb still refused to talk, Simcoe placed a hot sword on his chest. Caleb screamed.
Caleb after being tortured by Simcoe.
Later, Cooke finds Caleb barely conscious. He denounced Simcoe’s brutal interrogation tactics and worried that the Continental Army wouldn’t release the Woodhulls, given Caleb’s physical state. Before releasing Caleb, Simcoe quietly thanked him for the names he divulged in “the twilight of pain.”
Later, Amos Parker and Akinbode went to Caleb’s prison cell. Akinbode recognized Caleb and said that they once tried to kill each other years ago. They then carried Caleb out of the cell. One they arrived on the Connecticut shore. Caleb woke up and recognized Akinbode as a Queen's Ranger.
Trade gone wrong[]
Parker’s crew then brought Caleb to a mill to be traded for Abe and Richard, who had planned the trade with Ben. Ben then brought Abe and Richard outside for the exchange. Meanwhile, Simcoe’s Rangers quietly prepared their guns on the mill’s perimeter while Simcoe played pool at Rivington's Corner to give himself an alibi.
The Continental soldiers then handed over Richard in exchange for Caleb. A Ranger then recognized Akinbode from the perimeter. Akinbode heard the Rangers whistle and warned everyone that something was amiss. The Rangers opened fire and Richard was shot in the head, killing him. Walter Havens carried Caleb inside the mill, while Ben, Abe and two other men – Pitt and Spelling -- rushed inside as well.
Akinbode and his crew ran to the shore to escape in their boat, where he was soon left behind while fighting off three Rangers. He grabbed the dead Rangers’ guns and headed back toward the mill.
Pitt quietly bled to death from a gunshot wound next to Abe. Ben looked outside a window and counted the assailants. He saw one of the Rangers outside, Coffer, steal the bag filled with the 500-pound ransom. Ben voiced his confusion about why the men wouldn’t leave since they had the money, and Caleb said that they’re there to kill them. Havens tried to formulate a plan to talk to the men outside, but was shot dead while standing in front of an open window.
Ben saw that the men outside were preparing to burn them out of the mill. He soon found a tunnel leading outside and suggested that one of them sneak outside to create a flank. Abe volunteered despite Ben’s protests.
- "He must be in position by now, eh? You ready?"
"Always." - ―Benjamin Tallmadge and Caleb Brewster.
Ben and Caleb prepare to fight.
Abe used the tunnel to sneak outside with two pistols. He saw the Ranger Coffer looting from Richard’s dead body. He silently aimed one of the pistols at him, but pulled back when the other Rangers shouted to Coffer. Inside the mill, Ben, Caleb and Spelling rigged together a decoy plan.
The Rangers charged toward the mill with torches in hand. The mill door flew open. The Rangers opened fire on figures in the doorway, only to find that the figures were the corpses of Havens and Pitt.
Abe then shot at the Rangers from behind while Ben, Caleb and Spelling charged at them. Akinbode, who had returned to the mill's perimeter, shot at the Rangers, causing them to retreat. Coffer then ran off with the ransom money, but was chased by Abe, who pummeled him with his pistol. Coffer then strangled Abe, causing him to begin to lose consciousness. However, Abe was saved when Akinbode killed Coffer and took the money.
Later, Ben rode a wagon through the woods with Caleb, Abe and Richard’s body in the back.
Characters met[]
- Akinbode
- Benedict Arnold
- William Bradford
- Lucas Brewster
- Gamble
- Alexander Hamilton
- Walter Havens
- Thomas Hickey
- Gilbert du Motier, Marquis de Lafayette
- Amos Parker
- Robert Rogers
- Nathaniel Sackett
- Charles Scott
- John Graves Simcoe
- Anna Strong
- Selah Strong
- Samuel Tallmadge
- Robert Townsend
- Samuel Townsend
- George Washington
- Abraham Woodhull
- Mary Woodhull
- Richard Woodhull
- Thomas "Sprout" Woodhull
Relationships[]
Allies[]
Nathaniel Sackett[]
Charles Scott[]
Anna Strong[]
Benjamin Tallmadge[]
George Washington[]
Abraham Woodhull[]
Family[]
Lucas Brewster[]
Enemies[]
John Graves Simcoe[]
Behind the Scenes[]
Caleb Brewster was portrayed by Daniel Henshall in Seasons 1, 2, 3 and 4 of Turn: Washington's Spies.
Appearances[]
Episode
Turn: Origins (first appearance)- Turn: Washington's Spies - "Pilot"
- Turn: Washington's Spies - "Who by Fire"
- Turn: Washington's Spies - "Of Cabbages and Kings"
- Turn: Washington's Spies - "Eternity How Long"
- Turn: Washington's Spies - "Epiphany"
- Turn: Washington's Spies - "Mr. Culpeper" (referenced only)
- Turn: Washington's Spies - "Mercy Moment Murder Measure"
- Turn: Washington's Spies - "Challenge"
- Turn: Washington's Spies - "Against Thy Neighbor"
- Turn: Washington's Spies - "The Battle of Setauket"
- Turn: Washington's Spies - "Thoughts of a Free Man"
- Turn: Washington's Spies - "False Flag"
- Turn: Washington's Spies - "Men of Blood"
- Turn: Washington's Spies - "Sealed Fate"
- Turn: Washington's Spies - "Houses Divided"
- Turn: Washington's Spies - "Providence"
- Turn: Washington's Spies - "The Prodigal"
- Turn: Washington's Spies - "Gunpowder, Treason, and Plot"
- Turn: Washington's Spies - "Valediction"
- Turn: Washington's Spies - "Cold Murdering Bastards"
- Turn: Washington's Spies - "Benediction"
- Turn: Washington's Spies - "Hearts and Minds"
- Turn: Washington's Spies - "Hypocrisy, Fraud, and Tyranny"
- Turn: Washington's Spies - "Many Mickles Make a Muckle"
- Turn: Washington's Spies - "Judgment"
- Turn: Washington's Spies - "Mended"
- Turn: Washington's Spies - "Blade on the Feather"
- Turn: Washington's Spies - "Trial and Execution"
- Turn: Washington's Spies - "Spyhunter General"
- Turn: Washington's Spies - "The Black Hole of Calcutta"
- Turn: Washington's Spies - "Blood for Blood"
- Turn: Washington's Spies - "Nightmare"
- Turn: Washington's Spies - "Private Woodhull"
- Turn: Washington's Spies - "Our Man in New York"
- Turn: Washington's Spies - "Quarry"
- Turn: Washington's Spies - "Belly of the Beast"
- Turn: Washington's Spies - "Reckoning"
- Turn: Washington's Spies - "Washington's Spies"
Description[]
Season 1[]
- "In modern times, Caleb would be a member of Seal Team Six: the best of the best. Constantly at risk as a courier, he’s a man who relishes action and close scrapes. Bored with his childhood farm life in Setauket, Caleb jumped at the chance to see the world. At nineteen, he signed on to a whaleboat crew headed for Greenland where he braved icy waters and treacherous conditions in the hunt for sperm whales. Always the thrill-seeker, he’s faced down Mother Nature in all her glory and fury. As a result, the British do not intimidate him. Little does."
- ―Official description
Season 2[]
- "A vital member of the Culper Ring, Caleb acts as a courier, constantly putting himself at risk by relaying messages between Abe and Ben. Though very little intimidates him, Caleb was shaken to his core last season when Captain Simcoe executed his uncle right in front of him during the Battle of Setauket. Normally a man who relishes action, Caleb had advised Ben to wait before rushing headlong into battle and now harbors resentment towards him for his rash decision. Vowing revenge on Simcoe, he buries the rage he feels towards Ben, but his anger can only be held down for so long."
- ―Official description
Season 3[]
- "Caleb acts as a courier between Abe and Ben, constantly putting himself at risk to ferry Abe's intelligence from Setauket across the Long Island Sound and back to the patriot camp. A free spirit who marches to the beat of his own drummer, Caleb also takes on the dirty work that no one can know about. After watching Captain Simcoe kill his uncle at the end of the first season, Caleb is haunted by his decision not to kill Simcoe when he had the chance. Another opportunity to do so comes in Season Three, compliments of Abe's intelligence. Yet revenge will also rebound on Caleb, as his role in a morally questionable mission comes back to bite him."
- ―Official description
Season 4[]
- "Caleb acts as a courier between Abe and Ben, constantly putting himself at risk to ferry Abe's intelligence from Setauket across the Long Island Sound and back to the Patriot camp. A free spirit who marches to the beat of his own drummer, Caleb also takes on the dirty work that no one can know about. After watching Simcoe murder his uncle at the end of the first season, Caleb was haunted by his decision not to kill him when he had the chance. Another opportunity arose in Season 3, but things didn't go as planned and Caleb had to be saved by Robert Rogers. Rogers's interference eventually lead to Robert Townsend learning Caleb was the one who'd attacked his father, tearing a rift in the Culper Ring. A rift that only mended when they discovered Benedict Arnold was a traitor and rejoined to stop him. In Season 4, Caleb's carefree ways catch up to him, when he's caught up in Arnold's dragnet. His confidence is low and his inability to rise to the occasion when the Culpers need him most threatens to destroy not only childhood friendships, but the rebellion itself."
- ―Official description