Gambit Roulettes in fan works.
- In Aeon Natum Engel Gendo admits this is what his plans amount to. Although, considering the setting, all plans are at risk of becoming like this. Why? Well, because Nyarlathotep is a dick.
- Child of the Storm has Doctor Strange's plans initially appear to be this, before one very crucial thing is explained: Strange is not only a terrifyingly powerful Seer, but he's also a time traveller and Time Master, thanks to being altered by the Time Stone, meaning that he can see and predict more or less every possibility and arrange circumstances or manipulate people so that things turn out as he desires. Additionally, he's also shown not to be as infallible or omniscient as he likes to appear, something he points out himself (noting that it's part of a carefully constructed reputation). However, they do all tend to be hideously complicated.
- Harry Potter and the Methods of Rationality:
- Draco remembers a tragedy play his father brought him to see (an expy of Death Note), and at the end, Lucius asked him what the meaning of the play was. Draco mistook it to be as clever as the characters. His father chastised him, saying that any plan that requires more than three steps to succeed is unlikely to the point of worthless, and because only a fool goes with a plan that is barely possible, you really should never plan more than two steps.
- When Blaise Zabini works as a pawn for Dumbledore in the school armies, his Battle Magic teacher chides him for the plan, despite its success.Quirrell: In your future career, Mr. Zabini, I do not suggest trying any plots that complicated. They have a tendency to fail.
Blaise: Um, I said that to the Headmaster, actually, and he said that was why it was important to have more than one plot going at a time.
- Quirrell eventually explains that there are two types of plans: Plans that you want to succeed (which can be as complicated as you like, since they're not vital), and plans that you need to succeed (which should be simple and perfect). It also helps give you a reputation for blind luck and failure if you need people to think you're less competent than you really are. Case in point, his final plan in the story: He needs Harry to take him to the Mirror of Erised to get the Philosopher's Stone, but he merely wants to do so with his cover intact. So he sets up a series of coincidences which will lead Harry to believe Quirrel is dying and only the Stone can save him; this actually works perfectly, which is what tips Harry off to something being off—it was too improbable to happen on its own. When Quirrel realizes that Harry has deduced the truth, he just pulls out a muggle pistol and threatens him.
- The big Reveal at the end is that the entire story is one, put together by Dumbledore after he read (literally!) every single prophecy ever. Amazingly, even with this massive advantage, he still completely failed to predict how quickly Harry would defeat Voldemort. Thanks to the rat's nest of multiple complex prophecies he was working from even he has no idea how a lot of it is supposed to work; he ended up shooting for "humanity survives the aftermath" rather than a more specific plan.
- At the end of the Hero High Series. The main villain Pharaoh Alexander Sovereign nee Tempus reveals that his entire plan that he has practically set up throughout the series, was to stop his mother's crazy plan, revealing her to be the true villain. Or at least the eviler of two evils. He was also known to being infamous for his plans within plans, as well as fully understanding what a person is likely to do in the situation he presents them.
- My Little Avengers: It's eventually revealed that the entire plot was engineered by Loki in order to create a scenario wherein Big Mac is forced to willingly surrender Thor's power, allowing Loki to take over Equestria. It temporarily works and was only undone due to Pinkie Pie being a bigger Spanner in the Works than Loki anticipated.
- Sonic X: Dark Chaos: The whole Metarex war is merely a part of a gigantic conspiracy by Maledict the Devil in order to create a weapon powerful enough to defeat his enemies and conquer the universe.
- Death Note Equestria has one, of which Twilight's Memory Gambit is just one component. And she pulls it off masterfully, getting everything she wanted — L and Mer dead, her own name cleared as Kira, and putting herself in prime position to take control of the investigation.
- Parodied in Tealove's Steamy Adventure. Baron Zeppeli sits on his throne and watches the heroes through a crystal ball. As the heroes go through their adventure—including a number of events completely beyond his influence, such as getting captured by a cave troll, then escaping with the help of a pony they'd never met before—Zeppeli insists that every twist and turn is exactly as planned. The actual end goal of his plan is never stated, either.
- In Diaries of a Madman, Discord is bored. Very, very bored. He's been alive for millions of years because, as a spirit of chaos, he can't actually die while there are still sophonts on the planet, and he can't kill them directly because that would be in service to order. So he brings into existence a copy of the one person who can potentially kill him for good, and ultimately breaks his own plan by sending Nav into the past. The Stable Time Loop he creates causes him to weep for the first time in aeons. This is an Inverted Trope: the villain set things up so that all roads he could predict led to victory, but he just happened to land the ball on the 00. Everything else he does, however, is pretty much a Gambit Roulette.
- Thousand Shinji: The Warhammer 40,000 gods' plan was a very complex scheme, involving time-travel, several Batman Gambits and several dozens of different variables. And even so it went as planned. Justified because Tzeentch was planning it, and he plans for everything.
- There are so many factors that could have fallen the wrong way and doomed the yakuza's weapon shipment plans in Cries Unheard (a Lucky Star fanfic):
- To start with, where does Satoshi get the notion that Miyuki would have security information pertaining to her father's shipping company, which is not part of her own personal life? Incidentally, she actually had overheard certain things from said father, Jiro, but how could Satoshi have predicted that? (Let's also keep in mind that this is the reason Satoshi makes a point of isolating her and all her friends from one another and driving them to either suicide or hikikomori. Why didn't he just keep things simple and use some nude footage he secretly took of her to blackmail Jiro instead of her, and leave everyone else out of this whole thing?)
- The first thing he actually did, though, was walk over to Minami's front lawn after dropping Miyuki off at her house, and poison her dog, Cherry, in order to get all of Miyuki's other friends to gather there the next day, come over himself to "console" Minami, and get to know all of said friends. If Cherry was inside the house at that time, he'd probably just assume a different strategy instead, but there's even a one-shot Deconstruction Fic where everyone logically and rightfully suspects him the culprit and tell him off. Worse yet, they could place him under citizen arrest and call the police once he arrives, to say nothing of Konata asking Yui to come along (provided she's actually available) to arrest him once he arrives.
- After everyone's done consoling Minami, Satoshi then catches up with Tsukasa and Kagami, and invites them to the urban part of Tokyo to meet his friend and cohort Riku Kitamaru. Having not suspected him of anything yet like she should have, Kagami has no reason to turn down any small talk, but what if she declined to commute with him?
- Touching someone's hair the first time you meet her? Butterflies in her stomach or none, that's a great way to risk creeping her all the way out, Riku!
- To begin with, what if Kagami decided that she just wasn't into Riku, or if Konata decided she wasn't into Kenji?
- Part of Kenji's role in things is to keep Tsukasa and Kagami on some questionable terms, by feeding Tsukasa's illogical suspicion that Kagami has betrayed her in favor of her new boyfriend. To begin with, said suspicion started when it was narrated during Kagami and Satoshi's small talk that Kagami "ignored" Tsukasa the whole time. Not only is that Out of Character for her, but Tsukasa seemed like she was just standing on the sidelines waiting for either of them to speak to her, instead of actually contributing to their conversation like she does in canon. Also, how does it not occur to her that Kagami does have her own life as well, instead of existing entirely for her sake? But, now that that's already unfolded...
- The lies that he tries to feed her get undone once by Minoru (whom she's dating at that time). Kenji, whom she texted along with him to meet her to introduce to each other, subsequently abducts Minoru after he and Tsukasa part to torture him just for seeing her at all. What if Minoru didn't go anywhere conducive to said abduction? Also, Tsukasa lives with a loving family of six; if she believed Minoru about Kagami, then it's obvious that she and Kagami should be back on good terms, and any further attempts to brainwash her to suicide should not have panned out. They did have such a good time shopping together not much earlier on, and it's not like Kagami would snub her again after that.
- Not to mention the obvious risk of Minoru reporting what he did to him to the police. (For that matter, anyone could, no matter what you do short of just killing them to "ensure" that they don't. Especially Misao later on; more on her in a bit.)
- Also, charming as Riku may be, what if Kagami actually did suspect she was being stalked?
- Satoshi's advice to Kenji about Kagami: Treat her like royalty, so that they can see how long it takes her to offer her body to them, which she eventually does in return for being the only ones there in solidarity for her at Tsukasa's funeral. As if all it takes to a girl's pussy (and to avoid accountability for raping her friends) is to "be a nice guy".Pro tip
- Yes, nowhere like a crowded summer festival to stab someone (Konata) in the back to render her unconscious and abduct her, when it's more likely that she'll either die outright or scream in pain. That latter outcome is bound to draw attention to a knife-wielding thug like Kenji, but even that aside, one has to wonder why no one bats an eye at him carrying her limp body around instead of leaving it there and waiting for help to arrive (assuming they missed the part where he stabbed her in the first place).
- And when Konata wakes up again, Kenji threatens to murder Yutaka should she seek help from Yui. Did it not occur to him that Yui will probably be the one, along with Soujiro, to demand an explanation from her instead regarding her changes in behavior and Yutaka's absence ever since they all first met him, and how likely to break down and come clean she'll be once she finds no way out from them? Just how stupid does he assume a couple of folks he's only just met really are? (The fact that Yui really didn't pick up on this the whole time is a wallbanger in and of itself. I mean... )
- Riku and Kenji just so happen to be camping next to Misao and her family, when logically, they shouldn't be camping near anyone while abusing Konata. (They do have Yutaka hostage, but that's only a deterrent; should she decide at any point to beg for help anyway, killing her still won't prevent any repercussions that might unfold.) Misao spots them, strides over to say hi, and is subsequently raped and abducted. Those boys are lucky that her parents and brother somehow don't notice anything and either confront them or identify them for the police.
- And it's after this that the boys demand to know who else Konata and Misao are friends with, so that they can terrorize all of them too. The rest of those girls (besides Yutaka) currently have no idea that any of this is going on; why would they want to get them involved in this whole thing now and make more work and higher risk of arrest for themselves?
- Nanako dies in a traffic collision courtesy of the boys severing her car's brake cables. Sure, just do that one thing and let nature take its course. As if we don't have things called seatbelts and airbags designed specifically to prevent anyone from dying in a car wreck. Had she survived, how would they know where she'd have ended up before she could call the police?
- The author himself had deleted the fic in May 2016, after leaving it sitting at chapter 15 since November 10, 2014, specifically after realizing how utterly broken the storytelling was. Many additional variables that will never be accounted for would all have to unfold just the right way if those boys were to survive (at least for as long as they did) and have their arms deal go through (which still had yet to be stopped as of the flash-forward chapters that were already written).
- This motivational poster is part of Aizen's plan.
- Obscure example, but in GanXingba's Avatar: The Abridged Series, a comment is made mocking Zhao's — and Light's (Death Note) — ability to have plans that rely on perfect timing and actions they shouldn't be able to see coming.Zhao: [speaking of Zhao's denial of use of the Yu Yan Archers] Well darn, it looks like I'm out of luck barring a sudden promotion, like the one arriving right now.
Colonel Shinu: What!? There's no way you could have timed this down to the second!
Zhao: Of course I can. I went to the Light Yagami School of Strategy. I can practically predict the future.
- In chapter 15 of Harry Potter and the Pranking of the Multiverse, Dumbledore reveals that his plans were reliant on the local Harry choosing treacle tart as his favorite dessert. When the dimension traveling Harry questions the convoluted nature of this plan, Dumbledore explains that,"The more valuable success becomes, the more convoluted the plan must become."