Question: Who played a cunning an opportunistic pirate that had been quartermastered under the notorious Captain Flint?

Context articles: Billy Bowlegs Pirate Festival
Treasure Island (1920 film)
Missee Lee
Wild Cat (boat)
Captain Flint
Flint Phantoms
Toby Stephens
Peter Duck
Swallows and Amazons
Long John Silver

The Billy Bowlegs Festival grew out of a Labor Day ski show celebration back in 1953, which was the brainchild of some enterprising young businessmen, the JAYCEES, eager to latch onto a project that would warrant their time and efforts, be fun, and bring more tourists into the area.
 The idea of a Gasparilla-type observance centered on a “pirate” theme, and they unanimously chose as their patron pirate the notorious and legendary William Augustus Bowles, a pirate of controversial authenticity whose alleged dastardly deeds were widespread throughout the area.
 Nathan Fleet, a downtown Fort Walton Beach retail merchant at that time, was chosen as the first Captain Billy Bowlegs to reign over the Festival and lead the pirate “raids.”
 (In later years, his son, Judge Erwin Fleet, reigned as Cap’n Billy XIV.)
Treasure Island is a 1920 silent film adaptation of the novel by Robert Louis Stevenson, directed by Maurice Tourneur, and released by Paramount Pictures.
 Lon Chaney played two different key roles in this production.
 Charles Ogle, who had played Frankenstein's Monster in the first filmed version of "Frankenstein" a decade earlier at Edison Studios, portrayed Long John Silver.
Missee Lee is the tenth book of Arthur Ransome's Swallows and Amazons series of children's books, set in 1930s China.
 The Swallows and Amazons are on a round-the-world trip with Captain Flint aboard the schooner "Wild Cat".
 After the "Wild Cat" sinks, they escape in the "Swallow" and "Amazon", but are separated in a storm.
 Both dinghies eventually end up in the lair of the Three Island pirates, where they are held prisoner by the unusual Missee Lee, the leader of the Three Island pirates.
The Wild Cat is a fictional green two-masted schooner that Captain Flint, the Swallows, the Amazons and Peter Duck sail to the West Indies in Arthur Ransome's Swallows and Amazons book "Peter Duck".
 She also appears in the opening chapters of "Missee Lee".
Captain J. Flint is a fictional 18th-century pirate captain who features in a number of novels, television series, and films.
 The original character was created by the Scottish writer Robert Louis Stevenson (1850-1894).
 Flint first appears in the classic adventure yarn "Treasure Island", which was first serialised in a children's magazine in 1881, and later published as a novel in 1883.
The Flint Phantoms were a professional indoor football team based in Flint, Michigan.
 The Phantoms joined the Continental Indoor Football League (CIFL) in 2008 as an expansion team.
 They were the second professional indoor football team to be based in Flint, with the first being the Flint Flames of the original Indoor Football League.
 The Michigan Pirates played a home playoff game in Flint, in 2007, with the idea of moving there, but the team folded after the 2007 season.
 The Phantoms played their home games at the Perani Arena and Event Center in Flint, Michigan.
Toby Stephens (born 21 April 1969) is an English stage, television, and film actor who has appeared in films in both Hollywood and Bollywood.
 He is known for the roles of Bond villain Gustav Graves in the James Bond film "Die Another Day" (2002), (for which he was nominated for the Saturn Award for Best Supporting Actor), Edward Fairfax Rochester in a BBC television adaptation of "Jane Eyre" and in his role as Captain Flint in the Starz television series "Black Sails".
Peter Duck is the third book in the Swallows and Amazons series by Arthur Ransome.
 The Swallows and Amazons sail to Crab Island with Captain Flint and Peter Duck, an old sailor, to recover buried treasure.
 During the voyage the "Wildcat" (Captain Flint's ship) is chased by another vessel, the "Viper", whose piratical crew are also intending to recover the treasure.
Swallows and Amazons is the first book in the "Swallows and Amazons" series by English author Arthur Ransome; it was first published in 1930, with the action taking place in the summer of 1929 in the Lake District.
 The book introduces central protagonists John, Susan, Titty and Roger Walker (Swallows) and their mother and baby sister, as well as Nancy and Peggy Blackett (Amazons) and their uncle Jim, commonly referred to as Captain Flint.
Long John Silver is a cunning and opportunistic pirate who was quartermaster under the notorious Captain Flint.
 Long John Silver had a pet parrot called Captain Flint, often seen sitting on his shoulder where she would nibble on seeds.
 Silver claims to have served in the Royal Navy and lost his leg under "the immortal Hawke".
 "His left leg was cut off close by the hip, and under the left shoulder, he carried a crutch, which he managed with wonderful dexterity, hopping about upon it like a bird.
 He was very tall and strong, with a face as big as a ham—plain and pale, but intelligent and smiling."
 ("Treasure Island" (1883) by Robert Louis Stevenson page 82).
 He claims to have been the only man whom Flint ever feared.
 Like many of Stevenson's characters, there is more than a modicum of duality in the character; ostensibly Silver is a hardworking and likeable seaman, and it is only as the plot unfolds that his villainous nature is gradually revealed.
 His relationship with Jim Hawkins, the novel's protagonist and narrator, is interesting, as he serves as a mentor and eventually father-figure to Jim, creating much shock and emotion when it is discovered that he is in charge of the mutiny, and especially when Jim must confront and fight him later on.
 Although willing to change sides at any time to further his own interests, Silver has compensating virtues: he is wise enough to pay attention to money management, in contrast to the spendthrift ways of most of the pirates, and is physically courageous despite his disability; for instance, when Flint's cache is found to be empty, he coolly stands his ground against five grown men despite having only Jim, a boy in his teens, to back him.