The Life and Times of the Rev. Doctor Christopher Syn, Parson, Smuggler, and Sometime Pirate


by Matthew Baugh


Doctor Syn is one of the most interesting and unusual figures of the 18th Century.  A tall, slender, charismatic man with a commanding presence, Dr. Syn was a man who would have succeeded in any career.  Syn was a brilliant scholar and rousing preacher as well as being one of the finest swordsmen, riders, and seamen in all of England.  Unfortunately, Christopher's promising career was cut short when he was betrayed in love and left his calling to pursue a quest for vengeance across the world.

Years later Syn would return to the little town of Dymchurch-Under-the-Wall, seeking to resume the quiet life of a country parson, but his past would not let him go.  Learning that many of his parishioners were involved in smuggling, Syn resolved to protect them from the agents of the King's Revenue.  Assuming the masked identity of the Scarecrow, Syn led the smugglers in a series of adventures that rival those of Robin Hood, D'Artagnian and his companions, or El Zorro in their daring and their success.

Ironically, it may be in the masked Scarecrow that we see the truest picture of this complex man.  This guise allowed him to combine the compassion of the clergyman with the cunning and the swashbuckling style of the pirate captain.   

In compiling a time-line of the life of this man who was by turns, villain, hero, and tragic figure I have drawn heavily on the earlier brief time-line of Mr. Andrew Henry.  This has been extraordinarily helpful and I am deeply indebted to him.




Anthony Cobtree born.  (This date is conjecture and is based on the fact that Tony is said to be several years older than Syn.)


Christopher Syn is born in Kent.  I had originally written that Christopher had been born in Dymchurch but that is not stated in the novels.  A more likely birthplace would be Lydd, or possibly New Romney.  (Many thanks to fellow Syn fan Barry Marsh for pointing this out.)


April 6

Christopher's father and uncles are killed at the Battle of Culloden fighting on the Scottish side, leaving him the last male in the Syn line.  His mother dies of grief soon after and Christopher is raised by an elderly uncle.


Events of Dr. Syn On The High Seas


Young Christopher Syn first meets Mr. Mipps, who is on his way to a life at sea.  Syn saves Mipps from the King's Revenue and forges what will become a life-long friendship.

While a brilliant young Oxford scholar and Doctor of Divinity, Syn falls in love with the Spanish beauty Imogene Almago and rescues her from "Bully" Tappitt, whom he kills in a duel.

Syn and Imogene marry in a double ceremony with Tony Cobtree and his lady-love Caroline Gordon.  They return to Dymchurch-Under-the-Wall where Tony is the son of the local squire and Christopher is installed as Vicar.  (Caroline's maiden name is speculative, and is based on the fact that her maiden aunt is Agatha Gordon.)


Imogene is seduced away by Syn's supposed friend, Nicholas Tappitt, and Syn nearly loses his sanity out of rage and grief.

The birth of Imogene's son (While this lad is supposedly her son by Tappitt, Imogene will later reveal that he is actually the son of Christopher Syn.  His name is never revealed in the series.)

Birth of Charlotte Cobtree.  (Charlotte's birth is difficult to pinpoint.  In Dr. Syn Returns she is introduced as a girl of 19, but only a few days later she celebrates her 21st birthday.  I have assumed that the latter is the correct statement.)

Dr. Syn's odyssey in pursuit of Nick and Imogene begins.  He follows them to Spain, but they learn he is following them and flee to America.

When he follows, Syn's ship is taken by the pirate known as "Black Satan".   Syn kills the pirate in a duel and becomes the new pirate captain of the ship "Sulphur Pit".  He is aided in this by his old friend Mipps, who had been one of Black Satan's crew.


Syn abandons his ship and crew to go searching for Tappitt and Imogene in the American wilderness and Mipps comes with him.  Without Syn's knowledge Mipps has arranged a convenient accident which ignites the powder-hold of the Sulphur Pit, eliminating all witnesses who could tell of Syn's piratic acts.

Under the cover of taking a mission to the Indians, Dr. Syn and Mr. Mipps venture into the in the forests along the Mississippi.  They share several adventures with the Native American warrior Shuhshuhgah who becomes a loyal ally.


Birth of Maria Cobtree.


Syn emerges from the wilderness and learns that Tappitt has become a whaler and has taken Imogene and the boy on a voyage with him.  Syn becomes a ship's harpooner and adopts the alias "Clegg."  (The name Clegg comes from Shuhshuhgah's name for a vicious biting fly.)


Birth of Cicely Cobtree.


Syn completes his whaling voyage, having failed again to catch up with Tappitt and Imogene.  He learns that Tappitt is now in Kingstown Jamaica, where is known as "Black Nick."  He has purchased a fast ship, the "St. Nicholas," and letters of marque.  Syn steals the ship and it's crew from Tappitt and begins a new career of piracy.  He re-names the ship the "Imogene" and christens himself "Captain Clegg."  During this period he becomes the most infamous pirate of his day.


Birth of Dennis Cobtree.  (There is some uncertainty as to Dennis' exact date of birth, because of the problematic dates in Doctor Syn and Amazing Quest of Doctor Syn which are discussed later.)


A mutiny against Captain Clegg is incited by the Cuban mulatto who was the only survivor of the destruction of Syn's first pirate ship.  Clegg, Mipps, and Shuhshuhgah quash the mutiny and punish the mulatto by cutting out his tongue and marooning him on a coral shoal where he is certain to die.  Despairing of piracy and his quest for revenge, Clegg slips away from his ship.  His plan is to return to Dymchurch and live out his life as an obscure country clergyman.


The events of Dr. Syn Returns


November 13

A brig is wrecked on the rocks off of Dymchurch in the worst storm in living memory.  The only survivor is Dr. Syn, who is greeted by his old friend Tony Cobtree, now the Squire of Dymchurch.  Tony sees to that Syn is appointed Vicar of Dymchurch and Dean of Peculiars.

Syn is rejoined by Mr. Mipps, who has arranged yet another convenient powder-hold accident on the Imogene.  Mipps becomes the church sexton and the coffin maker for the town.

Mipps becomes involved in the local smuggling business.  When his activities attract too much attention from the authorities, Syn steps in.  He decides that the only way to protect his parishioners from the hangman's noose is to organize them so well that they will never be caught.  Adopting the masked identity of the Scarecrow he becomes adept at foiling the King's men at every turn.

A baby girl named Imogene is born to Black Nick and Imogene Syn, who have returned to England.  (Doctor Syn will later invent a story that little Imogene is actually the daughter of Captain Clegg and a Mayan princess.) 

Charlotte Cobtree, who has fallen in love with Dr. Syn, dies saving the Scarecrow from the King's men.  Her death nearly shatters Syn's grip on sanity, but he manages to recover.

Dr. Syn finds Imogene on her deathbed and forgives her before she dies.  She also tells him that he is the true father of her son, and that Tappitt left the lad somewhere in America.  (At the novel's end Syn dispatches Shuhshuhgah to America to try and locate the youth, but neither is heard from in the series again.)

Black Nick is arrested and hanged.  Before his death he confesses to being Clegg the pirate in return for Syn's promise to care for his daughter Imogene.


Events of Further Adventures of Dr. Syn

The story begins on a "...wet and sild November night."  Dr. Syn is now thoroughly committed to his dual life as the kindly Vicar of Dymchurch and the mysterious Scarecrow.


Maria Cobtree marries a French aristocrat and moves to Paris.  (This date is speculative.)


Events of Courageous Exploits of Dr. Syn

The Scarecrow's career reaches a swashbuckling high as he thwarts the King's Revenue, the British Navy, and the Prince of Wales himself.


Dr. Syn is a member of the first League of Extraordinary Gentlemen.


Events of Amazing Quest of Dr. Syn

A lawyer and a tontine involve Doctor Syn in an adventure that takes him to Wales to contend with a rival smuggler named Dolgenny.

(We are told early in the story that the year is 1780, but internal evidence makes this impossible.  Dennis Cobtree's age is given as 17, and a difficult schoolboy named Jerry Jerk makes an appearance.  Jerry is only 12 in Doctor Syn and could not yet have been born in 1780.  The date of 1790 works so well here that I assume "1780" to be a typo.)


The French Revolution begins.  Maria and her aristocratic husband are in constant danger living in Paris.  Their will eventually be jailed and he will be executed by the revolutionaries.


Events of Shadow of Dr. Syn

Cicily Cobtree and the Scarecrow rescue Maria from the Reign of Terror.  Monsieur L'Epouvantail (as the Scarecrow is known in France) manages to thwart both the British Revenue agents and the efforts of Robespierre in this adventure.  The only person he cannot outwit is Cicily Cobtree, who has fallen in love with him and discovered his secret.  Sadly, like her sister before her, Cicily dies while saving the Scarecrow from a trap.  When Cicily dies Syn nearly loses his sanity for the third time in his life.


Events of Dr. Syn

In Captain Collyer the Scarecrow finally meets his match.  Not only is the Captain clever enough to discern that Syn is both the scarecrow and the nefarious Captain Clegg, he also has working for him the Cuban mulatto who Syn and Mipps have long believed dead.  The story ends with Syn dead at the hands of the mulatto and the Romney marsh smugglers shattered.

It is a very different Syn who appears in this story, less cunning and far more blood-thirsty.  Though the last in the series, this was chronologically the first book to be written.  It may be that Syn's biographer, Russell Thorndike, relied on more sensational sources which made his subject out to be more of a villain than he really was.  It may also be that this is a wholly accurate account of Syn's final days, and that the death of Cicily really was the final blow his sanity could endure.

The book presents us with several historical impossibilities.  Thorndike tells that the only thing that saved the Romney Marsh smugglers from execution was that captain Collyer was called away by the onset of the Napoleonic wars the day after Syn's death.  When Collyer died in the war, the secret of the smugglers died with him in 1791.  Unfortunately the source material is too badly corrupted to be certain.

Imogene, who has been raised as Syn's adopted daughter, marries young Dennis Cobtree.  (Imogene gives her age in Doctor Syn as "Sixteen, or perhaps seventeen..." and Dennis is described as being "...eighteen summers." old.  If the Doctor Syn were actually set in 1794 then Dennis would be 21 and Imogene would be 19.  While this is not a perfect solution, is is much better than the 1802 date, which would make them 29 and 27 years old.)


October 21

Captain Collyer is killed in action at the Battle of Trafalgar.  Whatever he had learned about the Romney Marsh smugglers dies with him.

Mr. Mipps, having escaped Captain Collier and fled England, has become a person of some importance in a Buddhist Monastery above the city of Poyang.  There he delights the monks with his eerie stories of the Romney Marsh and the mysterious Scarecrow and his night riders.

As a last practical joke, Mipps sends a letter to Collyer to set him on a futile quest for a non-existent treasure.  Unfortunately, the letter doesn't reach England until after Collyer's death and goes unread for a century.

December 1923     

The events of The Slype

Some residents of the city of  Dullchester find Mr. Mipps' letter and engage in their own treasure hunt until they discover it is a fraud.  (Rick Lai writes: "The Slype involves a murder which occurred before World War I, but the murder is revealed decades later by a stained glass painting in a church. The painting is supposed to be a "war memorial."   Various references in the novel indicate that the war was World War I, but the most unambiguous reference is on the last page (chap. 46, p. 330) which mentions the memorial in the context of "the Great War."  The novel takes place in December as shown by the celebration of Christmas in the penultimate chapter (chap. 45).   December 15 falls on a Saturday (chap. 42, p. 278), which indicates that the year is 1923.")



The Life and Times of Doctor Syn was created for the sole purposes of entertainment and information. All rights reserved. The text of this page is 2000-2004 by the author, Matthew Baugh. The design of this page is 2000-2004 by Win Eckert. No copying or reproduction of this article or any portions thereof in any form whatsoever is permitted without prior written permission and consent of the author.