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Venturous Smuggler

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An often-romanticized character archetype found in many genres, portrayals of the smuggler can range from a Lovable Rogue Running the Blockade to subvert an oppressive government, to a slimy criminal profiteering off scarcity. Most fiction seems to agree, however, that it takes considerable guts to repeatedly risk the wrath of both the authorities (if you get caught with illegal cargo) and the clients (if you lose said cargo).
Sub-trope of Lovable Rogue. Sister trope to Gentleman Thief, Intrepid Merchant, and Bold Explorer. May also overlap with Courier.
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In Reaper Man, Miss Flitworth's father was a reciever of contraband, and her firm moral absolutism includes that she's absolutely sure there's nothing wrong with smuggling. It appears this is common in Sheepridge, since it's suggested that the reason everyone was suspicious of Bill Door's strangeness was that they thought he might be a revenue man.
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Duke from Haven captains his own cargo ship and is a self-described "businessman," though his business is almost always below-board. This is somewhat of an Open Secret in town, with the Haven Police Department and even the Coast Guard knowing what he's up to (and he makes little effort to hide it), but nobody even tries to bust him. For reasons unexplained. He's definitely of the Lovable Rogue variety, with his heart in the right place, and a surprisingly strong moral compass for someone whose living involves being paid to transport contraband.
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Vahanian is a mostly straight example in Chronicles of the Necromancer: as the Lovable Rogue the heroes come for to help, with one exception. He has a personal history with Arontola and is quick to agree to work for the heroes because of it, rather than how most of this trope are Heroic Neutral.
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 Chronicles of the Necromancer
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The Romney Marsh smugglers are the heroic figures in the Doctor Syn ("The Scarecrow") books, supported by the local population for the wealth they bring to the area.
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 Doctor Syn ("The Scarecrow")
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The Kingmaker Histories has the international smuggling/thieving duo of Iyer and Winterlich: General Services who save Colette's life in the Seltsamwald.
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 The Kingmaker Histories (Podcast)
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Blades in the Dark lets you play an entire smuggling crew, specializing in carrying contraband, arcane goods, weapons, or passengers under the nose of the Imperial authorities and organized crime.
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Discworld:
Vetinari is (secretly) willing to tolerate some smuggling in Ankh-Morpork, seeing it as a good way to keep people smart (both the smugglers and the customs police).
Chidder in Pyramids is always quick to say his family is in commerce, and always vague about what that commerce is. Teppic isn't particularly surprised to notice that his merchant ship, the Unnamed, seems to have a much smaller hold than you might expect from the outside, and also a hidden ramming spike.
In Reaper Man, Miss Flitworth's father was a reciever of contraband, and her firm moral absolutism includes that she's absolutely sure there's nothing wrong with smuggling. It appears this is common in Sheepridge, since it's suggested that the reason everyone was suspicious of Bill Door's strangeness was that they thought he might be a revenue man.
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Deconstructed, like so many other romanticist tropes, in A Hero of Our Time: Danko from Taman is first presented as a larger than life figure that challenges the elements to visit a loved one across the sea, but once Pechorin realizes he and his girlfriend are just smugglers, he is majorly disappointed and stops caring about them.
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James Bond's ally Columbo in For Your Eyes Only. He cheerfully admits that he is a smuggler, but he does not smuggle drugs. That is the purview of his Archenemy (and the Big Bad of the movie) Kristatos.
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The Dark Knight: They never appear on-screen, but Batman hires a crew of South Korean smugglers to help him kidnap a Chinese money launderer from his home base in China. The implication is that they're this trope.
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 The Dark Knight
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In Revolver (1973), Vito and Ruiz employ Carlotta, a female smuggler who makes a living running people across the Italian/French border, to smuggle them from Italy into France. She also serves as Ruiz's Love Interest.
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Booster Terrik was a successful smuggler with close ties to the Rebellion, and a personal friend of Rebel pilot Wedge Antilles, until Booster was caught by the Corellian Security Force and sentenced to five years in the spice mines of Kessel. Upon his release he tried to go back to smuggling but found that the solitude of hyperspace was too similar to the crushing boredom of the mines, so he gave his Pulsar Skate to his daughter Mirax (who became a successful smuggler herself) and entered quasi-retirement, negotiating on others' behalf rather than running his own business. Booster played a major role in The Bacta War, and when an Imperial captain surrendered to him personally during a Brandishment Bluff, Booster found himself the first civilian in the galaxy to own an Imperial II-class Star Destroyer. After some negotiation, he was allowed to keep the partially-disarmed warship, which he renamed the Errant Venture and turned into a mobile resort/bazaar/casino. It wasn't quite a happy ending, though — Booster soon found that managing a capital ship that size was a major headache and hellishly expensive (especially his decision to repaint it red), and his daughter Mirax ended up marrying Corran Horn, son of the very CorSec officer who arrested Booster.
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Star Wars: The Old Republic lets you play one: The Smuggler is one of the four Republic-aligned character classes and a thinly-veiled Expy of Han Solo. Their storyline has them rise through the criminal underworld from Running the Blockade on Ord Mantell to becoming the Voidhound.
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It's fairly common for player characters in Traveller to at least dabble in smuggling, especially given the multi-megacredit mortgages on their ships.
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Talon Karrde, introduced in The Thrawn Trilogy, is a mix of this and Knowledge Broker. His organization managed to pick up most of the pieces of Jabba the Hutt's criminal empire after Jabba's death, and Karrde himself has a reputation as a respectable and trustworthy business partner - as much as a smuggler can be trusted, anyway. Karrde tried to remain neutral in the Galactic Civil War, but eventually Defaulted to Good, helped the New Republic defeat Grand Admiral Thrawn, and went on to help them and the Imperial Remnant make peace in the Hand of Thrawn duology. His personal ship is the Wild Karrde.
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 The Thrawn Trilogy
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Girl Genius: The "Wulfenbach Dark Fleet" were mentioned briefly in the comic, but given a bit more detail in the novel Agatha H. and the Siege of Mechanicsburg. Rumors portray them as a group of dashing rogues who skirt Baron Wulfenbach's laws by smuggling goods around his vast airship fleet to those in need. There is absolutely no evidence that they actually existed, and the Baron was getting rather impatient that no one was filling the obvious niche.
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The Transporter is a modern take on the classic archetype. Frank Martin is a consummate professional who gets paid for bringing things from point A to point B, no matter how many cordons he has to run or mooks he has to punch out. His vehicle of choice in the first film is a heavily-customized BMW 7-series.
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Davos Seaworth from A Song of Ice and Fire is a former smuggler captain, who was so good at Running the Blockade to deliver food to Stannis Baratheon's besieged army during Robert's Rebellion that Stannis knighted him for his services — right after chopping off four of his fingertips in punishment for his earlier crimes.
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Dash Rendar of Shadows of the Empire is a Suspiciously Similar Substitute for Han Solo, who of course is frozen in carbonite for the duration of the story. He's brash, cocky, an expert pilot and gunslinger, and owns the flashy Corellian YT-2400 light freighter, The Outrider.
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Chidder in Pyramids is always quick to say his family is in commerce, and always vague about what that commerce is. Teppic isn't particularly surprised to notice that his merchant ship, the Unnamed, seems to have a much smaller hold than you might expect from the outside, and also a hidden ramming spike.
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Blow: George Jung likes to portray himself as this type of Lovable Rogue, even waxing poetic in court about "moving plants over an imaginary line".
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Solo established that Lando Calrissian was already an accomplished smuggler before he and Han met, and lived a far more ostentatious lifestyle.
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In Lucifer's Star by C.T. Phipps stars Cassius Mass, who is a navigator later captain of a huge freight hauler. He eventually turns to smuggling as a way to supplement his legitimate income. He is somewhat different from other examples because his spaceship, the Melampus is the size of a small town and he's closer to a Rogue Trader from Warhammer 40,000 than Han Solo.
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Scum and Villainy, which is based on Blades, has the Stardancer starship/crew archetype, which specializes in space smuggling and is heavily based on Serenity from Firefly and the Millenium Falcon from A New Hope. Among Player Characters, the Scoundrel playbook in particular is inspired by archetypal smugglers like Han Solo and Mal Reynolds.
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Warhammer 40,000: A Rogue Trader is an independent ship captain who's equal parts smuggler, pirate, explorer, and mercenary. Many are used as Inquisitorial agents (knowingly or not), especially where the smuggling of forbidden xenos artifacts is involved.
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Blake's 7: A member of the elite Alpha class, Jenna was a beautiful but cynical smuggler/self-styled "free trader". She clearly had some involvement with resistance groups (most likely smuggling supplies to them) as she had once met the resistance fighter Avalon. She was captured by the Federation and sentenced to be transported to the prison colony on Cygnus Alpha. However, she befriended Blake, assisted in a mutiny on the transport ship and escaped with him and Avon aboard the Liberator. A talented pilot, Jenna initially took charge of all navigation duties aboard the Liberator. She was the only crew member capable of piloting the ship when Zen was inoperative or unwilling to do so.
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Casablanca: Rick Blaine used to be an Arms Dealer for the Spanish Republic, and now specializes in helping refugees from Europe passing through Casablanca, for a price.
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 Casablanca
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The Count of Monte Cristo: Edmond is rescued by a group of smugglers when he escapes prison and quickly becomes The Ace among them, later secretly recruiting them for his many plans.
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Star Wars Legends:
Talon Karrde, introduced in The Thrawn Trilogy, is a mix of this and Knowledge Broker. His organization managed to pick up most of the pieces of Jabba the Hutt's criminal empire after Jabba's death, and Karrde himself has a reputation as a respectable and trustworthy business partner - as much as a smuggler can be trusted, anyway. Karrde tried to remain neutral in the Galactic Civil War, but eventually Defaulted to Good, helped the New Republic defeat Grand Admiral Thrawn, and went on to help them and the Imperial Remnant make peace in the Hand of Thrawn duology. His personal ship is the Wild Karrde.
Dash Rendar of Shadows of the Empire is a Suspiciously Similar Substitute for Han Solo, who of course is frozen in carbonite for the duration of the story. He's brash, cocky, an expert pilot and gunslinger, and owns the flashy Corellian YT-2400 light freighter, The Outrider.
Booster Terrik was a successful smuggler with close ties to the Rebellion, and a personal friend of Rebel pilot Wedge Antilles, until Booster was caught by the Corellian Security Force and sentenced to five years in the spice mines of Kessel. Upon his release he tried to go back to smuggling but found that the solitude of hyperspace was too similar to the crushing boredom of the mines, so he gave his Pulsar Skate to his daughter Mirax (who became a successful smuggler herself) and entered quasi-retirement, negotiating on others' behalf rather than running his own business. Booster played a major role in The Bacta War, and when an Imperial captain surrendered to him personally during a Brandishment Bluff, Booster found himself the first civilian in the galaxy to own an Imperial II-class Star Destroyer. After some negotiation, he was allowed to keep the partially-disarmed warship, which he renamed the Errant Venture and turned into a mobile resort/bazaar/casino. It wasn't quite a happy ending, though — Booster soon found that managing a capital ship that size was a major headache and hellishly expensive (especially his decision to repaint it red), and his daughter Mirax ended up marrying Corran Horn, son of the very CorSec officer who arrested Booster.
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Malcolm "Mal" Reynolds from Firefly fits this archetype, as the swashbuckling Lovable Rogue captain of an interplanetary smuggling crew. His first mate Zoe and right-hand man Jayne do as well.
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The following is a list of statements referring to the current page from other pages.

 Venturous Smuggler
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Bravery Tropes
 Venturous Smuggler
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Characters as Device
 Venturous Smuggler
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Criminals
 Venturous Smuggler
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Organized Crime Tropes
 Venturous Smuggler
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Pirate Tropes
 Revolver (1973) / int_45d4d694
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Venturous Smuggler
 The Dark Knight / int_45d4d694
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Venturous Smuggler
 The Girl in the Bikini / int_45d4d694
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Venturous Smuggler
 Agatha H. and the Siege of Mechanicsburg / int_45d4d694
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Venturous Smuggler
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 Ex-Superheroes / int_45d4d694
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 Lucifer's Star / int_45d4d694
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 Realm Breaker / int_45d4d694
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Venturous Smuggler
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Venturous Smuggler
 The Legend of Anne Bonny / int_45d4d694
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Venturous Smuggler
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Venturous Smuggler
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Venturous Smuggler
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Venturous Smuggler
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Venturous Smuggler
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Venturous Smuggler
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 Starchaser: The Legend of Orin / int_45d4d694
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