Doctor Syn : Clergyman, Smuggler, Pirate, Missionary, Duellist ...Russell Thorndike's creation was a man of many roles and identities,but has not yet appeared in a HoTT list, as far as I know.

By day, Doctor Syn was the respected vicar of Dymchurch and by night "The Scarecrow", the leader of the smugglers on Romney Marsh in the last decades of the 18th century.

Stronghold : A smuggler's train of heavily laden pack mules or a church/vicarage or Mother Handaway's cottage with the hidden stable

Alternatives :

Doctor Syn duelling (Blade) or tricking his opponents (Magician) either of which would allow him to be the General also.
Jimmie Bone impersonating the Scarecrow as a decoy (Hero).
Charlotte Cobtree as another decoy for the scarecrow (Hero).
George (IV) Prince of Wales (God).
Shuhshuhgah - an American Indian (Sneaker)
L'Epouvantail - the Scarecrow's boat (Water Lurker)

For Doctor Syn's time as Captain Clegg, the Generic Pirate list could be used

The list above includes Syn/The Scarecrow twice, as both a sneaker and a hero, reflecting the character's deception of his enemies in often appearing to be in separate places and bypassing the rule of a Sneaker not being permitted to be the General. As Doctor Syn, the character frequently made his way into the homes, camps andstrongpoints of the enemies of the Scarecrow to take prisoners or to release captive people or contraband, which can be represented in HoTT by a Sneaker's attack on a Stronghold.However, if the 'Enemies of The Scarecrow' use Heroes, Doctor Syn might be better portrayed as a Magician, who entraps them.

I have not given a separate classification for Mipps, Doctor Syn's henchman, expecting him to be based with his master, whether as a Ship's Carpenter to Captain Clegg, sexton to Doctor Syn or Hellspite, 2nd in command of the Night Riders, with the Scarecrow.

Jimmie Bone can be shown as either a Highwayman, 'Gentleman Jim', or as a leader of the Night Riders, 'Beelzebub' or as dressed to impersonate the Scarecrow.

The Night Riders and Marsh Witches were the elite of the Scarecrow's smugglers and wore wild black rags and masks, while the masks and their horses' heads should shine with "phosphorescent light" - luminous paint ?

Classifying the Prince of Wales as a god is not a suggestion that there was anything godly about the future George IV, but does seem to model his involvement. The high PIP cost represents Doctor Syn's having to travel to London to request a favour from the Prince, while the likelihood of the 'god' disappearing reflects the Prince's fickle and capricious nature. The Prince 'destroys' the Scarecrow's enemies by promoting them with immediate effect to posts well away from Romney Marsh and the interests of the Scarecrow. He can support the Scarecrow's forces by issuing a Royal Pardon to release them if they are captured.

Stronghold : Dover Castle or an Admiral's flagship or any military camp with prisoners or smuggled goods to be rescued ( possibly with Doctor Syn preaching nearby )

Alternatives:

Sneakers/Lurkers (Merry, Colonel Delacourt/Black Nick and Captain Vic, Revenue/Excise Men, Bow Street Runners, Smuggler Traitors etc.)
Blades (Captain Raikes, The Dandy Sleuths, Captain 'Bully' Foulkes, etc.)
Water Lurkers (Revenue/Excise or naval boats )
Rider General (Captain Faunce of the Dragoons )
Horde General (Admiral Troubridge or General Troubridge )
Heroes (as an alternative to Blades and Riders for the Naval or Dragoon Officers )
Hordes (Any of Syn's enemies mounted on horses "blown" by having just been used by the smugglers on a run.)

The Mulatto was marooned by Captain Clegg and so has a score to settle with Clegg/Syn/Scarecrow.

Most of the Scarecrow's enemies were defeated easily by him - after writing 'Doctor Syn', Thorndike filled 6 prequel novels with the Doctor/Scarecrow's successes - but the Naval Captains seem to have done better than the hordes of other failures.

Russell Thorndike's novels
Doctor Syn on The High Seas
Doctor Syn Returns
The Further Adventures of Doctor Syn
The Courageous Exploits of Doctor Syn
The Amazing Quest of Doctor Syn
The Shadow of Doctor Syn
Doctor Syn

The story has also been used in a few films :
"Doctor Syn" (1937),
Disney's "Doctor Syn Alias The Scarecrow" (1963),
Hammer Horrors' "Captain Clegg" (UK) / "Night Creatures" (US) from 1962

http://sunflower.singnet.com.sg/~tonym/drsyn.html
http://homepages.tesco.net/~davyo/drsyn.htm
http://www.drsyn.com/

I do not know of any specific figures available currently for the Night Riders / Marsh Witches. In 25mm Redoubt Enterprises produce a Doctor Syn figure and some 18th century smugglers, Outpost Wargames Services produce a Highwaymen range and Pirate ranges and Seven Years War ranges are available from various manufacturers

Ral Partha and West Wind Productions produce scarecrow figures, but I believe these will appear too modern unless converted.

In 15mm use Pirate and Seven Years War Ranges. Press Gang/Naval Landing Party are available from Tabletop Miniatures (Cardiff) or Freikorps (ERM)

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