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Opportunistic Bastard
We all know The Chessmaster: he's got a plan ready to go months in advance, with every detail jotted down. If that plan fails, he's got backup after backup already in place.

Then you've got this guy. The Opportunistic Bastard doesn't have a plan, or at least not a clearly outlined one. He may have a vague goal that he's working towards, but when it comes to getting there, he's winging it. Other times the Opportunistic Bastard doesn't even have that going for him, and just latches onto other people's schemes in the name of making as much short term profit as he can.

As the name suggests, characters like this excel at grabbing onto the opportunities that others present. Unlike The Chessmaster, who often fails when things don't go according to plan, the Opportunistic Bastard typically rolls well with unexpected results, exploiting every new circumstance to his own advantage. Where they tend to suffer is in the long term—a good opportunist can keep his head above water on any given day, but is ultimately going to crash and burn because they lack the vision to stay in it for the long haul. A particularly capable Opportunistic Bastard might actually be able to give the impression of being a Chessmaster, due to their ability to adapt to new situations, but even then, they are liable to paint themselves into a corner due to their lack of forethought.

Opportunists of this type are usually motivated only by their own self-interest. If their actions do benefit someone else, it's either accidental, or because that person belongs to the select group of people that our opportunist actually cares about. Similarly, they are rarely loyal to any cause larger than their personal self-advancement; if an Opportunistic Bastard has an ideology, it is likely to be ill-defined, self-serving, and/or shallow. As a result, this character is liable to be an antihero at best, and outright villain at worst.

Hierarchically they could be anyone from a minor character to the Big Bad himself. Compare/contrast The Chessmaster. See also Manipulative Bastard and Xanatos Speed Chess. Can easily become a Wild Card. Likely to be a Dirty Coward or to suffer from Chronic Backstabbing Disorder. Might belong to Les Collaborateurs or even become The Quisling.


Examples:

Anime & Manga
  • Char Aznable in the original Mobile Suit Gundam is a competent planner, and is able to stay a step ahead of most people, but he's more of a short-term opportunist than a long-term schemer, and more often than not is flying by the seat of his pants. He has the vague goal of "eliminate the Zabis" but no real plan for doing it—instead he just hangs around with them, hoping to get the chance to murder them. He hangs around with Garma Zabi, and is able to betray him, leading to his death in battle. He then just bounces around from commander to commander and mission to mission until the very end of the show when he's able to take a shot at Kycilia Zabi, who by then (no thanks to Char) is the only Zabi left. He spends most of Zeta dodging responsibility, and hoping the AEUG will force the world to follow his father's philosophy without him having to lead it; when things go south, he abandons the cause after his defeat by Haman Khan. Even in CCA, when he does take power in Neo-Zeon, it's not through planning—he just waits until everybody else with a claim to the throne (Haman Khan, Glemmy Toto, Mineva Zabi) is dead or in hiding, and declares himself leader.
  • Madara Uchiha of Naruto had a plan and an actual claim to Chessmaster status before his resurrection. However, he was returned to life with a series of mishaps: his former apprentice having hijacked his old plan and him being revived by the dark Impure World Resurrection technique, and since then has been trying to improvise his way to victory. Madara proceeded to wait for an opportunity to break free of the caster's control before finding his apprentice Tobi had already revived the monstrous Ten-Tailed Beast. Madara immediately seizes control of it and manipulates Tobi until he can force him to revive Madara at cost of his own life. Even when the first attempt fails, Madara makes the resurrection of his former Arch-Enemy work to his advantage by draining his powers to bolster Madara's own to the point where he's even stronger when he fully revives.
    • Uchiha Sasuke is no better; his role as an antagonist is a series of him merely betraying a more ambitious and powerful villain and hijacking their resources or achievements for his own use. First Orochimaru, then Akatsuki and then Kaguya. At the conclusion, he finally executes his master stroke, waiting until all of the most powerful threats amongst the heroes and villains had eliminated each other, with only Naruto to stop him.
  • Puella Magi Madoka Magica: Arguably, Kyubey. While they do have a goal in mind, they are shown to exploit new circumstances to try and manipulate girls into contracting (best example: he waits until Mami is literally dying in a car crash before appearing) and invoke Exact Words, Literal Genie and You Didn't Ask to conveniently hide the (multiple) uncomfortable facts of being a Magical Girl. Also, he tends to cut corners while granting wishes as a means of conserving energy; making the phrasing of each girl's wish essential.

Film
  • Hans from Frozen who admits to not having a real plan. He first intended to woo Elsa. When he realised she was an Ice Queen, he turned his attentions to her sister, Anna, intending to arrange an accident for Elsa. Then Elsa reveals her powers and runs away, with Anna in pursuit, and he tries to ingratiate himself to the public while they are gone. Finally, when Anna comes home, he tries to have her killed, then tells the assembled nobles that they got married, making him king; when she and Elsa turn up alive he tries to kill them both to cover his tracks. At no point does he have a master plan; he's just aiming to be king through whatever means are available.
  • Pirates of the Caribbean: While in the first film Jack Sparrow was shown to rely on the Batman Gambit quite a bit, the other films have also shown him to be quite the opportunist as well, and sometimes, it's not clear which one he is, this or The Chessmaster.
    "Do you think he plans it all out or just makes it up as he goes?"
  • Kraven of the Underworld film franchise has no loyalty to anyone or anything but his own ambition. When spared from death by his own cowardice at the hands of the Lycan werewolves' leader Lucien, Kraven aligns himself with Lucien's plans to seize power for himself in the vampire covens. Kraven seizes on a chance to allow Lucien's Lycans to massacre the vampire elder Amelia, and when his treachery is exposed, he later betrays and murders Lucien before taking advantage of the resulting power vacuum from the large scale battle at the conclusion of the second film to attempt to murder the final sleeping vampire elder and rule the coven. Lacking his own plans, Kraven simply ingratiates himself to whoever is in power for his own success and has no compunction taking any chance fate gives him in pursuit of it.

Literature
  • A Song of Ice and Fire:
    • Bronn intends to rise in the world anyway he can, and attaches himself to anybody who can do that for him. Starting out as a simple sellsword, he first latches onto Catelyn Stark's revenue transporting Tyrion Lannister to the Vale, for the possibility of a reward. He then proceeds to quickly switch sides from Catelyn to Tyrion, championing him in a Trial by Combat, thus becoming the right-hand man of one of the richest and most powerful men in the Seven Kingdoms. He stays on for a while, accumulating riches, titles and a knighthood, before eventually refusing Tyrion's request to champion him again in the trial over Joffrey's murder because Cersei Lannister offered him a marriage into a powerful noble house with no risk to himself. Seizing any opportunity that came his way, Bronn went from an ordinary mercenary all the way to the Lord Protector of House Stokeworth.
    • Lord Walder Frey, head of House Frey and Lord of the Crossing, only reacts to the plans of others and only openly aligns with anyone when he believes it will serve his best interests. In the backstory it's established he didn't join Robert's rebellion against the Targaryeans until it was all but confirmed Robert would be victorious, earning him the nickname "The Late Lord Frey." In Game of Thrones he only joins Robb's war with the Lannisters when Catelyn grants him generous enticements, including a marriage between Robb and one of his daughters. When Robb breaks his marriage vow, Walder happily latches onto Tywin's side when he offers Walder the position of new Lord of Riverrun. Lord Walder then proceeded to butcher Robb and most of his bannermen when they were defenseless and assumed themselves safe under Lord Walder's roof; a pragmatic move that made Lord Walder one of the most powerful, and despised, men in all of Westeros.
    • Brown Ben Plumm, the commander of the sellsword company, the Second Sons. Prior to his promotion, Ben first works for Yunkai as another mercenary defender. However, after Daenerys defeats his company and causes their leader, Mero, to disappear, Ben becomes the company's new leader and joins Daenerys against his former employers. He stays with her until she conquers Mereen at which point, believing she can't win against the newly reformed Yunkai forces and having found out she can't control her dragons, he abandons her and again allies himself with Yunkai. When he believes Daenerys is about to become a Dragon Rider, however, Ben plans to sell out Yunkai again and realign with Daenerys. He's also a man who notices golden opportunities when presented with them. At a slave auction, he tries to buy Ser Jorah Mormont and Tyrion Lannister. The former he plans on killing and presenting as a "wedding present" in order to get back into Daenerys's good graces. The latter he plans on selling for the bounty on his head, which includes a lordship in Westeros. Eventually Tyrion is able to talk Ben into allowing both him and Jorah to join the company, but only after convincing him he can give Plumm vast more riches as Lord of Casterly Rock than he can as a head on a pike. Ben is a man of no loyalties, who will backstab anyone if the odds aren't in their favor, and who is driven by a lust for riches and self-preservation above all else. Plumm believes that successful and long-lived sellswords like himself are opportunistic bastards at heart, and those that aren't tend not to be very long-lived.
  • Obadiah Hakeswill, Richard Shape's Arch-Enemy from the Sharpe series is a toadying sadist of a British drill sergeant with his only goals being his own profit and enjoyment. Hakeswill relishes bullying the men in his command, but throughout the India Trilogy, he is quick to desert the British whenever he thinks he has a better shot with the local rulers. He deserts and betrays the British no less than three separate times there and murders the colonel who could have exposed him. In the Napoleonic Wars in Spain, Hakeswill returns and continues attempting to weasel his way up in rank before he takes a chance to desert the British and captains a group of Bandits where he opts to Rape, Pillage, and Burn for for fun with no greater goal in mind.
  • Cavilo from The Vor Game is the leader of a mercenary company who has no qualms about betraying her employer if she gets a better offer from someone else. After capturing her at the end of the book Miles gives her a Reason You Suck Speech about it.
    You should have stuck to your original contract. Or your second plan. Or your third. You should, in fact, have stuck to something. Anything. Your total self-interest did not make you strong, it made you a rag in the wind, anybody's to pick up.
  • Benna Murcatto of Best Served Cold is an amoral snake of a man who latches on to his talented elder sister Monza while she uses her skills in strategy, tactics and combat to bring them to higher positions. Benna's role seems to be deciding who to betray and when, while charming his way into the good graces of others. When they're taken in as kids by the mercenary Nicomo Cosca, Benna has him deposed when he realizes Monza is more popular than Cosca. when they attack a city known as Caprile, Benna takes the chance to 'lose' Monza's orders to spare the populace to benefit him further. Finally, it's revealed Benna was going to double cross their current employer, Duke Orso, if Orso hadn't acted first to kill Benna before he got the chance.
  • Lucius Malfoy of Harry Potter is a Smug Snake of an opportunist, latching onto anything that will either help his ambition or help him save his own hide. He doesn't usually have a plan either—he'll let somebody else do the thinking, and try to benefit from their work. In the backstory, he joins Lord Voldemort for the power involved, and also because its racist cause adhered with his prejudiced mindset. After Voldemort's power is shattered and the Dark Lord disappears, Lucius abandons his master and pretends his deeds were because of brainwashing, allowing him to escape justice. Perhaps the best example of Lucius's "planning capabilities" is how he orchestrated the opening of the Chamber of Secrets. He simply plopped Tom Riddle's diary into Ginny Weasely's lap, let Tom Riddle do all the work, and sat back, taking advantage of the chaos for his own ends. When Lord Voldemort returned to power in Harry Potter and the Goblet of Fire, Lucius goes back to Voldemort to avoid incurring the Dark Lord's wrath, and once again carries out Voldemort's will. Throughout the series, Lucius only has one consistent loyalty and that's to his family. Eventually, when Voldemort's cause endangers his son's life, Lucius defects from the Death Eaters for Draco's safety.
  • In the Ciaphas Cain books, Cain himself rarely goes into a situation with a concrete plan for how to tackle it (or even, at times, a complete picture of what he's actually getting into), but he has a remarkable tendency to find and exploit any advantage that could possibly give him an edge when he's in the thick of things. Interestingly, he's one of the rare few examples of this trope who's self-aware enough of just how shallow his motives run and who has enough of a conscience to actually beat himself up over it in quieter moments (that is, if we take his own account at face value).

Live-Action TV
  • Angelus in Season 2 of Buffy the Vampire Slayer has no real plan beyond "screw with Buffy". It isn't until the last few episodes that Acathla arrives and gives him an actual goal to work towards, and even that falls into his general attitude of "I will be as big a dick as I can."
  • Justified lends itself to characters of this type by its very premise. With all the competing families and gangs, there will always be those looking to exploit the chaos to their own advantage. Some of the more notable include:
    • Johnny Crowder, Boyd's power-hungry cousin, who never missed a chance to improve his own position at the expense of others. Whether it was backing Boyd against Devil's internal coup, blackmailing Colton Rhodes about his drug addiction, providing the US Marshals with information, or manouvering between genuine power players like Boyd, his Uncle Bo, Wynn Duffy, Nicky Augustine, Hotrod Dunham, and Mr. Yoon, Johnny would grab at any chance to make a profit or increase his chances of taking over the Crowder family. Even after gaining control of Hotrod's organization in Season 5, he doesn't have a plan, beyond "hurt Boyd as much as possible", which leads to his defeat at the hands of his chessmaster cousin. Driven by greed and revenge (he held Boyd responsible for his crippling, and superb at playing the odds, Johnny could survive almost any situation, but the conclusion was never in doubt.
    • Season 5's Daryl Crowe Jr. is described as such by his right-hand man, Jean-Baptiste, who comments on Daryl's penchant for finding employ with someone else, and then making their business his. He did this to the Muchado family's sugar smuggling operation in Florida. After coming to Kentucky he first tries to take over his cousin Dewey's brothel, leading to conflict with Boyd Crowder, then hires himself out to Boyd as an enforcer. Most recently, while on a job for Boyd in Mexico, he and his brother Danny have sabotaged Boyd's operation for as yet unrevealed reasons. If anything, this unpredictability, and general lack of attention to detail makes Daryl more dangerous, as nobody can really anticipate how he'll try to take advantage of the situation, only that he will.
    • The same season gives us Mara Paxton and Sheriff Nick Moony, both of whom bounce back and forth between working for Boyd and working for Lee Paxton (Mara's husband) based on whoever seems strongest at the time, in an attempt at getting the best possible position for themselves. Moony had a history of this sort of behaviour long before Season 5, selling out Doyle Bennett to Boyd, Tillman Napier to Boyd, and then Boyd to Paxton, all based on who was offering the most at any given time. His refusal to just pick a side in the Boyd Crowder/Lee Paxton war is what ultimately gets him killed.
  • Torchwood: Miracle Day had Jilly Kitizgenger. An opportunist, fast talking PR rep, she was mostly concerned with getting work. She represented the evil cooperation and the crazy murderer/child molester even she admitted was off putting, but her loyalties lie with whatever will get her to the top. Before approaching the murderer, she approached a doctor working with the heroes for the exact opposite goals.
  • Gaston Bullock Means from Boardwalk Empire is a shameless manipulator and back-stabber who acts only to swindle as much money as he possibly can out of whomever he's currently conning. Means spends most of his time in season three Playing Both Sides on the Nucky Thompson and DA Daughtery power struggle, waiting to ally himself with whichever one comes out on top. In season four, he again pretends to be on Nucky's side only to sell out information about him to the FBI to save his own ass. Even when he's being raided by the CIA he spends his remaining seconds trying to extort increasingly exorbitant amounts of money out of Nucky for information on The Mole in Nucky's organization.
  • Black Sails has John Silver (later to be known as "Long" John Silver) who is a self described opportunist and will latch onto any chance to advance his position or at least keep himself from getting killed. When told that in a few months his usefulness will be gone and he will probably be killed he merely sees this as a time to make friends with his captors. Most of the other major characters have some sort of plan or goal they are working toward but Silver simply jumps at any opportunity that presents itself and goes where it takes him.
  • Crowley from Supernatural has worked his way from a demonic salesman to the King of Hell by working his way into various situations, betraying those he works with and being fully willing to subvert situations to his benefit. He takes advantage of Dean and Sam's wish to kill Lucifer to aid them while keeping his involvement secret. Crowley later uses Sam and Dean to defeat Lucifer, and takes the opportunity to seize control of Hell by becoming its king. Crowley spends the next few seasons playing up and shifting alliances with various characters, always ready to seize an opportunity when it presents itself.
  • Calvin "Cheese" Wagstaff of The Wire is defined by his ambition and his utter lack of loyalty to anyone. Cheese starts out as an enforcer and lieutenant of his uncle, the notorious drug kingpin "Proposition Joe." When Marlo Stanfield begins his rise to power, Cheese promptly aligns with him for a bigger slice of the pie and betrays his uncle to his death. He then aligns with Marlo instead. When Marlo is no longer in the picture, Cheese tries to seize control of the loose alliance of Drug Dealers, basically admitting his shifting loyalties and opportunism in front of them.
  • Ashur from Spartacus: Blood and Sand decides, after he is crippled by the Gladiator Crixus, that his only goals in life are revenge and rising in power. Using his cleverness to ingratiate himself to his master Batiatus, Ashur becomes his errand boy and supporter, hoping to tie his fortunes to Batiatus's own. When he is indebted to Gladiator named Barca, Ashur quickly makes it appear as if Barca has betrayed Batiatus and arranges his death. Ashur takes advantage of Batiatus's gratitude to steal Crixus's lover, and after Batiatus falls, Ashur simply aligns himself with Praetor Gaius Claudius Glaber, and uses Spartacus's rebellion to get Glaber to assign him his own private squad of enforcers with which he terrorizes Capua. Ashur uses his intelligence and lack of morality to make himself invaluable to those he serves while simultaneously using their favor to push himself higher.

Video Games
  • Final Fantasy IX: This trope applies to Kuja, from disc 3 onward. In the first two discs, Kuja had a true Evil Plan, but it gets immediately curbstomped the second that his boss, Garland, decides that he has outlived his usefulness. Kuja immediately goes into hiding and, with his treachery revealed, has no choice but to acquire power any means he can. He tries a few things that also fail, before opportunity shines and one of the good guys taps into their Super Mode right in front of him. From that moment on, his plan is to let the heroes fight both him and Garland, and win, and then Turn Red and invoke his own Super Mode permanently. And it works. At that point, Kuja had everything he needed to take over the world, but there was one thing he didn't count on...
  • Benny from Fallout: New Vegas. The Big Bad Wannabe of the game, Benny wants to seize the city of New Vegas for his own but has little in the way of actual planning ability. In the backstory, he killed the chief of his tribe in a duel to the death and supplanted him because the former leader wanted their people to remain nomadic rather than take the more profitable route of joining the New Vegas leadership. Though nominally aligned with New Vegas's "autocrat," Mr. House, Benny really craved more power and had one of Mr. House's securitrons reprogrammed to spill all of Mr. House's secrets. The securitron, Yes-Man, told Benny about a platinum computer chip that could be used to upgrade the securitrons of New Vegas into unstoppable killing-machines, and then formulated plans on how Benny could foil Mr. House's plans while hijacking the platinum chip for Benny's own use. Benny was an ambitious man who forged alliances as often as he broke them, but it's made abundantly clear that he was only a danger because he leeched off the plans of those smarter than himself, such as Mr. House and Yes-Man, for his own use.
  • Dimitri Rascalov of Grand Theft Auto IV, a man with serious loyalty issues starts as the number 2 to the unstable Russian gangster Mikhail Faustin. When protagonist Nico Bellic shows up, Dimitri takes his chance to manipulate Nico into murdering Mikhail so Dimitri can take over. He then tries to have Nico killed as well by quickly allying with Ray Bulgarin, an old enemy of Nico's. Dimitri spends the rest of the game getting friendly with those who can aid his pursuit of wealth and power, and will betray anyone in an instant if he finds a better opportunity in it.
  • Queen Anora from Dragon Age: Origins will manipulate or backstab anyone so long as it satisfies her two goals: remaining in power and securing the physical safety of her father, Loghain. Being a choice-based game, there are a number of options for how Anora will react if certain decisions are made. Should the Player Character, the Warden, decide to back her at the Landsmeet, she will turn against her father, the regent, to secure power for herself. However, should the Warden decide to back Alistair instead, she will betray the Warden and side with her father, despite the fact Loghain had arranged her husband's death, conducted numerous evil actions, and doing so risked a civil war in Ferelden even as the Archdemon led the Darkspawn to Rape, Pillage, and Burn the country. In order to preserve her political power, Anora will also go through with political marriages, such as she will to a Noble Human Grey Warden, seeing him as a popular figure. She'd even go so far as to marry Alistair, the bastard brother of her beloved, late husband, the very same man she'd also order executed for being a threat to her in another possible play through where she rules alone. Anora has no master plan to get her way and few scruples, she'll simply latch on to anyone who is most likely to give her the power she wants and do as they ask in return. The one exception to this is marrying whoever personally executes her father. That is the one thing she will not do no matter the benefits.
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