They are ruthlessly efficient. They apparently have no trouble recruiting the vilest, evilest, nastiest, deadliest scum of the earth into their ranks. They are dedicated to power and glory and Taking Over The World! Against them, the world's only hope is the best of the best, frequently equipped with the latest weapons and an unlimited budget. In the end it comes down to the bravery, daring, skills and luck of the good guys...
...well, it would if the enemy leader wasn't a complete moron.
For some reason, villainous organizations which have no problem with kidnapping, blackmailing, threatening the destruction of the world, or even kicking puppies, somehow tolerate having an idiotic leader whose inept schemes for world domination are always foiled, often because of the utterly bizarre plans and implementation that General Failure himself is responsible for. Oh, they might bitch and moan about the dumb ideas, but it's not like they'll ever do anything about it.
Occasionally, The Watson, the Meta Guy, or other Genre Savvy characters will question the Big Bad's ludicrous schemes, but since they're not in charge, that will be it. Very often The Starscream is the only one who opposes the leader at all, making him look like the Only Sane Man on their side.
Common phrases of the General usually include "I wrote themanualon military tactic X" or "This reminds me of the time we fought enemy X in an improbable location, what a tale that is!".
General Failure may have started out as a competent commander in a position of less importance, and his success led to him being promoted beyond his capabilities. If this is the case, then it's a villainous example of the Peter Principle. If he started out as an incompetent mook or private, you can expect his rise to be an improbable series of Kicked Upstairs, Uriah Gambit and Promoted to Scapegoat that never deliver on the bad ending or being the only living replacement left when his superiors keep dying.
Most of the time the leader is also a Bad Boss, which can lead to We Have Reserves. One wonders sometimes if the good guys are secretly making sure the doofus on top stays there. General Failure is essentially the personification of Failure Is the Only Option, and is the eventual destination of severe Villain Decay. He often bears similarities to The Neidermeyer, but on a much higher scale. Compare Armchair Military, Miles Gloriosus, Modern Major General. Pointy-Haired Boss is a similar non-military trope.
Contrast Four-Star Badass, General Ripper, Colonel Badass, Sergeant Rock and Surrounded by Idiots.
This trope does not happen as much in the Real Life. Really incompetent officers usually never even graduate from the military academy: incompetent officers mostly don't tend to get promoted past Captain (Lieutenant Commander in Navy) level. Most real life officers appearing as General Failures are simply unlucky ones (and conversely many military geniuses just got lucky and afterwards announced I Meant to Do That). Historically there was more room for nepotism and many military commissions could be bought or were awarded on class rather than merit. But even then there were limits to how much incompentence you could show before getting demoted, some of the people repeteadly dying under your command decided you got hit by a stray arrow or were simply wiped away by a side with more competent leaders.
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Anime and Manga
Spandam from One Piece is an abnormally vicious variation, with some of his schemes (such as framing Tom) actually coming to fruition. Yet he's still incompetent enough to mistake a Nuclear Football for his cell phone. It's actually In the Blood since his father Spandine was about the same however Spandine unlike his son draws the line at killing civilians and his own men, judging from his reaction to Sakazuki doing both.
Granted they both do look like snails with buttons and speakers attached, and he wasn't looking at it when he pressed the button and started talking. It still is a major fuck up for the guy. He should have made sure he got the right one or kept the Golden Den Den Mushi in a more secure pocket he isn't going to touch.
Gundam 00 gives us Klaus Grad. His victories are purely the result of Celestial Being and all his forces do is blow up, and provide other targets to distract the A-Laws. The only time Kataron actually helped Celestial Being in a meaningful way is due to someone else defecting from the A-Laws and becoming the General for that battle. However, it must be noted that he is quite aware of this, and thus insists on being the rear guard while Celestial Being does the heavy lifting, and he spends most of his time providing support (resupply and shelter) because he KNOWS that all he's realistically able to do, pretty much making him an inversion of this trope.
It should be noted that this is less due to any incompetence on Klaus's part and more to the sheer overwhelming technological superiority of the A-Laws who have the latest generation GN weapons while Kataron is relegated to using outdated mobile suits from the previous era, with its leaders being well aware that they are fighting a losing battle and thus dedicating more of their efforts towards attempts to disseminate information about the A-Laws' atrocities among the public rather than confronting them directly.
The one time Kataron does have a remotely even playing field because of the anti-beam gas, they manage to Curbstomp the A-Laws, so he isn't a failure if he isn't screwed from the beginning.
Lord Djibril, the leader of Blue Cosmos in Gundam SEED Destiny is rather infamous for this. He's admittedly not half bad at suckering other people to fight for him, but all of his war-winning schemes either blow up in his face spectacularly or are implied to succeed only because the true Big Badallowed them to. Luckily for his side his Hypercompetent Sidekick, Neo Roanoke was usually on hand to mitigate the worst of it. Unluckily for everyone else in series, Djibril's plans always failed, but they usually took thousands of people with them.
Yuna Roma Seiran was worse. An example of Armchair Military at its worst, he managed to make Djibril (who at least managed to kill lots of his opponents) look brilliant by comparison.
Justified in Fullmetal Alchemist, the Big Badwants blood to create a giant transmutation circle so he intentionally has the ruler of Amestris put idiots as Generals since they are easy to control, and their incompetence will not only kill the enemy but their own men as well.
Subverted in Dragon Ball with the Red Ribbon Army. The leader, Commander Red, has been hunting for the Dragon Balls for months and his men have been routinely slaughtered by Goku. He wants the Dragon Balls so he can wish to become taller. However, his subordinates don't know that and when his second in command, Adjutant Black, finds out (he assumed they were going to wish for world domination) he executes Red in disgust and becomes leader of the Black Ribbon Army.
Despite being an extremely good Chess Master who out-gambited the Big Bad of the series several times, Kabuto Yakushi of Naruto has shown to be a General Failure throughout the War Arc. Edo Tensei who should have steamrolled the opposition, such as Deidara or Sasori, are sacrificed extremely early on for stupid reasons and there isn't even a proper attempt in the manga to free Deidara after he's been captured. Sasori, despite being resurrected isn't even given his second scroll of puppets to fight with thus robbing him of his poison and his entire arsenal. Kinkaku and Ginkaku are sealed as well-given them their personalities was the worst choice that Kabuto could have done since they worked-as Kinkaku demonstrated, far better as pseudo-Jinchuriki berserkers. Hanzo the Salamander and Nagato, perhaps his second and third/fourth most powerful Edo Tensei are sealed-the latter given a pathetic performance since Kabuto doesn't even give him his normal field of vision. And despite having four Kages, he loses all four consecutively. The only times when he plays it smart are with Zabuza and Haku, as well as Madara Uchiha which actually scores some wins.
Groo The Wanderer is this whenever he ends up in charge, to the point where his enemies rejoice.
Cobra Commander from G.I. Joe. The walking, talking (well, screaming and whining) example, especially in the animated version. Note that in the comics version, a civil war eventually did erupt within Cobra specifically because of his repeated failures, and he had repeated challenges for his top spot, even though that version of the character was actually competent and did pull off a win now and then.
The Adult Swim miniseries G.I. Joe: Resolute subverts Cobra Commander's usual tendencies, while acknowledging them. Cobra Commander states that he was merely using Obfuscating Stupidity to dig up traitors and have his subordinates think outside the box, but that it is no longer useful. Therefore, he becomes much more menacing and less tolerant of failure.
The concept behind the joke was parodied in a MAD spoof of Star Trek.
Spock: Captain, we are under attack. Should I call for General Alert?
Kirk: Where is he?
Spock: This is no laughing matter, Captain. We have a major disaster here!
Kirk: In that case, have General Alert and Major Disaster report to the bridge — at once!
In The Transformers (IDW), Starscream ran the Decepticons into the ground with incompetent leadership during the two years Megatron was in traction. Megatron claims in his "The Reason You Suck" Speech that he doesn't fear Starscream's treachery but rather his incompetence.
Dr. Evil, in the Austin Powers movies. Keeps trying to blackmail the world with absurd schemes, even though Number Two is making the organization truckloads of money legitimately.
Admiral, later Emperor Pirk in Star Wreck. Only his incredible luck and keen tactical eye explain why he ever advanced beyond Ensign on his military career.
Parodied in the Bulldog Drummond spoof Bullshot. War hero 'Bullshot' Crummond keeps running into former members of his WW1 regiment "The Royal Loamshires" who have been mutilated in various ways due to his incompetence.
Though no specific generals are pointed out, this is the general message in Iron Eagle, where the protagonist (Doug Masters) has to steal an F-16 from the Air Force to save his dad because the government won't do anything about Doug's dad being held by an un-named Arab country somewhere in "the Med."
Admiral Kendal Ozzel from Star Wars. In the EU, he once served in the Clone Wars and was willing to senselessly sacrifice hundreds of clones and Jedi to win, and when things start to go south, he would surrender to save his own skin. The only reason why he even got such a high position was because he has connections with Palpatine.
The events of Zulu occur as the result of the Battle of Isandlwana, at which the British expeditionary force of 2000 sent to crush the Zulus had been destroyed due to the incompetence of their leaders that the Africans took maximum advantage of.
The second Night at the Museum film has the reanimated General George A. Custer, who has more bravado than good sense. His great plan to surprise the enemy is to loudly announce his decision to attack before attacking. When the flaw is pointed out, he thinks for a while and comes up with a "better" plan: loudly announce they're not going to attack, and then attack.
In Kagemusha, Katsuyori Takeda disregards the defensive strategy set by his father and the other generals, with catastrophic results.
In Ran, Jiro deliberately ignores Kurogane's veteran military wisdom and commits to foolhardy strategies that ultimately lead to the destruction of his kingdom.
The 1968 version of The Charge of the Light Brigade is made of this trope. Very much Truth in Television here.
Visser Three later Visser One from the Animorphs embodies this trope. That's what you get for having a society basically built on Asskicking Equals Authority - The Peter Principle kicks in and your stealth invasion ends up being run by a guy who kills his own troops at the slightest provocation. The heroes occasionally work to keep him in charge, but hamstrung by the 'stealth' aspect.
Right now, most of the Solarian League Navy's brass falls under this trope. Many of them only hold high rank due to high-level connections (either as members of naval "dynasties" or through family ties to major defense/industrial contractors), and are arrogant enough to believe that, despite the League having had no major combat experience in centuries, that they know everything there is to know about fighting a space war.
Admiral Daala, from the Star Wars Expanded Universe, is described as a tactical and strategic prodigy, yet her attempts to strike back at the New Republic were easily foiled. It is debatable, whether this was caused by poor planning and disorganization, or by good guys having Suncrusher-grade plot armor when written by her creator, infamous K.J. Anderson. Her only lasting achievement was acknowledging her own failures and uniting the remaining Imperial forces under a single leader rather than a group of feudingwarlords, which in fairness did lead to the Imperial Remnant getting behind her co-conspirator, the very awesome Pellaeon, and she may have gotten better byLegacy of the Force. Other books offer an array of explanations for Daala's failures - it's mentioned that she excelled at infantry tactics, while her war against the New Republic was waged by fleet. Death Star offers an Retcon suggesting that she suffered brain damage at some point, while there's a long-standing rumor that she earned her rank at least partially by being Grand Moff Tarkin's lover (true or not, it's unwise to mention this in Tarkin's presence; the last guy who did got Thrown Out the Airlock with his spacesuit's comlink on so everyone could listen to how sorry he was as his orbit decayed).
More than a few Expanded Universe villains fall under this by following Emperor Palpatine's "make a giant superweapon with a convenient weak point" tactic. The ones who don't have a high chance of being written by Timothy Zahn.
General Lord Ronald Rust from Jingo, part of the Discworld series, a man who believes nursery stories qualify as military precedent and will deliberately pursue a moronic strategy because the enemy won't expect it.
Subverted with Kitiara of Dragonlance- she looks like she's losing a lot, but is very good at snatching victory from the jaws of defeat. She'd have you believe this was all part of her Evil Plan, though it's more likely she's just very good at improvised Xanatos Speed Chess until she gets backstabbed by the one minion she thought was loyal... Also, she was winning handily, despite being hampered by incompetent and backstabbing superiors and colleagues, until she had the misfortune to face perhaps the greatest military genius in the history of Krynn.
In The Crystal Shard, Akar Kessel decides to magically enslave an army to conquer all he surveys. If he knew anything about commanding an army, he might have actually won. It's repeatedly Lampshaded by both Errtu and the Crystal Shard itself, who both offer him good advice that he continually rejects, mostly to indulge his Control Freak tendencies.
In the Star Trek: Enterprise Relaunch novels, Romulan Praetor D'deridex insisted on opening up a front at Haakona despite the Romulans being occupied fighting a full-out war with the Human/Andorian/Tellarite alliance. Admiral Valdore had no choice but to follow orders, despite knowing a war on two fronts would be a disaster for Romulus.
Mentioned in Harry Harrison's The Stainless Steel Rat Wants You, where one of the first hostile actions of the aliens against humanity is the kidnapping of the top brass of the Space Navy. Their subordinates immediately took over the responsibilities, vastly improving the efficiency of the fleet.
Desdel Stareye, a night elf commander of La Résistance during The War of the Ancients. While his predecessor, Kur'talos Ravencrest, was an experienced general (if a bit too political for his own good), Stareye was incompetent and only got to a commanding position due to his status as a nobleman. He hated non-elves and relegated tauren, furbolg, and earthen (proto-dwarves) to support roles, despite them being at their best on the front lines. He also refused to listen to Rhonin, Broxigar, and Krasus, despite the latter posing as an elf, even though all of them have plenty of experience fighting the Burning Legion. His "grand" battle plan involved the combined army marching at the enemy in a staggered formation, whose "tips" were supposed to break through the enemy lines. While this worked at first, this was revealed to be a trap, resulting in many casualties, including Stareye himself. After his death, the lowborn Jarod Shadowsong took command and proved to be at least as (if not more) competent as Ravencrest. He also actively supported integrating the non-elven troops into the army. After the end of the war, Jarod became one of the leaders of the night elf society.
"Captain America" in Generation Kill is described as this, but most of the soldiers seem to just ignore him.
In AS Ong Of Ice And Fire Edmure Tully is a minor example, being defeated in almost every battle. The one time he manages to win one it ends up screwing up his side's longer term strategy.
The Limper frequently clashes with The Black Company in the series of the same name. He never wins, and ends each confrontation a little more disfigured than before, until he's finally just a head strapped to a wicker body.
Most flag officers in The Lost Fleet thanks to the Forever War with the Syndicate Worlds having an extremely high attrition rate. As a result, complex fleet tactics are forgotten and Attack! Attack! Attack! mentality is prevalent with each ship individually charging at the enemy for a slug-out mostly relying on the "fighting spirit" and the captain's personal honor. By the time Geary is awoken from cold sleep, he is the most brilliant tactician in the galaxy by virtue of remembering anything at all about fleet tactics. Most admirals by this point are more politicians than fleet commanders, providing suggestions and making proposals to ship captains, who then vote on whether or not do follow them. Geary puts an end to that, reinforcing the chain-of-command and discipline.
In the spin-off series, now-Admiral Geary rescues a bunch of POWs from a Syndic world. All of these turn out to be high-ranking Alliance officers, one of whom immediately demands to take command of the fleet, claiming seniority over Geary. Someone points out that both the Alliance government and fleet HQ has given Geary command over the First Fleet and tasked him with a critical mission. The rescued officers brush him off, claiming that no one cares what the politicians want. Some of the, though, point out that they've spent years (or decades) in captivity and have no idea on the current state of affairs. Naturally, Geary is having none of that and delegates the responsibility of dealing with them to someone else. Of course, Desjani once again reminds him that he should have kept his rank of Fleet Admiral instead of demanding to be demoted.
Live Action TV
Colonel Klink from Hogan's Heroes, an example where the good guys were going out of their way to keep the idiot in charge.
Interestingly, this was at the insistence of Klink's actor, Werner Klemperer. Klemperer's Jewish family fled Germany during the Third Reich, and he later enlisted in the American army to help fight in World War II. He consented to play Klink only on the condition that Hogan and company would always win the day and that Klink was portrayed as a complete idiot rather than a competent Nazi who's simply outplayed by the heroes.
Then there was this series' version of Field Marshal Haig, whose primary battle plans involved British soldiers walking slowly across the battlefield, which had already been tried 18 times without success.
Colonel Flagg from M*A*S*H. Not exactly a "villain," but a certainly an "antagonist" who always fails in his "intelligence" missions.
Most combat commanders on M*A*S*H regardless of which side they're on get this treatment, as the central conflict is the medical staff versus everyone else (and particularly the people running the war).
General Steele attempts to be a frugal leader, but ends up showing his crazy side when he attempts to have Hawkeye court-martialed, going all out when he starts singing and dancing.
General Iron Guts Kelly wanted to die fighting, but died in Margaret's arms instead.
The series portrays just about everyone above the rank of captain in this manner, with a few exceptions, most of them doctors. All generals are shown to be career-minded war-mongers who have little care about the lives of the soldiers they lead.
A wonderful counter-example is the British Maj. Ross, played by Bernard Fox, in the 6th season episode "Tea and Empathy". His apparent callous heartlessness to his wounded men is his way of reassuring them that they will fully recover. The initial conflict between him and Hawkeye, and the reconciliation after the reveal, are both very well played. Taken even further with their Flurry clusters whose assigned commanders so incompetent they're not good enough to lead Solahma Cannon Fodder, which is the primary role of the clusters.
Li'l Abner: Jubilation T. Cornpone, a satire of overly romanticized Confederate generals.
The franchise features more than a few Imperial generals who fit this description, officers who got their ranks through family connections and have never been in actual combat. Their strategies tend to center around the fact that the Imperial Guard has a lot of men in it, and if you throw enough of them at the enemy you'll eventually win. Some generals even manage to screw that up. This is brought into even sharper relief by a few examples of pragmatic, tactically solid military leadership, for instance Lord General Zyvan of the Ciaphas Cain series, who once actively avoided picking a fight with the Tau because the crappy backwater planet they were on wasn't worth the effort, and is quite good at putting limited resources where they can do the most good.
Canonically, Abaddon the Despoiler is one of the most feared figures in the galaxy, an unstoppable warrior with the willpower to unite the factions of Chaos into devastating Black Crusades, a psychopathic champion of the Dark Gods who has put off his own ascension to daemonhood just so he can continue to slaughter Imperials in the mortal realm. Fanonically he's an incompetent halfwit (with no arms) who finds ways to lose despite having billions of followers, the support of all four Chaos Gods, and ten thousand years to plan and execute his schemes. The main excuse for Abaddon's lack of success (besides Status Quo Is God) is the fact that the Imperium has spent ten thousand years fortifying the passage out of his base in the Eye of Terror, and is willing to throw any number of soldiers at him until he's forced to retreat. Other sources point out that Abaddon's Black Crusades are typically built around an objective such as swiping an insanely potent daemon sword or the Blackstone Fortresses, while the most recent codex suggests that Abaddon's plan is simply to cause so much carnage in the material universe that the Warp spills over and vomits out hordes of daemons, allowing him to overrun Terra.
Other Chaos champions get to deal with fickle patrons who will abandon them regardless of their battlefield successes. After all, Tzeentch is literally the god of backstabbing, while Khorne doesn't care which side gets slaughtered so long as blood has been spilled.
Orks generally subvert this. Suicidal frontal charges? Bombs hitting your own side more than the enemy? Other Hollywood Tactics? Dat's the right and propa way to fight! It's only when some warbosses suggest un-orky tactics like a feigned retreat or using camouflage that the boyz start grumbling (and the boss has to start crackin' heads).
This makes sense for them, considering their biology. If an Ork gets torn to shreds on the battlefield, the spores it releases will eventually grow into more trouble for said enemies than that one Ork ever was. How aware the Orks are of this is unknown - and academic.
Vlad Drakov, a permanent guest of the Ravenloft setting, has this enforced on him as his darklord curse. Previously, he had been a successful mercenary general who was nonetheless treated with disdain by the rulers who hired him and his men and had aspired to rule a land of his own. After being taken into the mists, he found himself ruling Falkovnia, a domain under perpetual martial law, where soldiers were the most respected of professions and he ruled with an iron fist. However, his section of real estate was surrounded by domains ruled by women and fops, not the men of war he wanted to be recognized by. He tries constantly to invade other lands, but the Demiplane itself will never allow him to win, even against the relatively puny and undermanned forces of his neighbors. And with every crushing defeat (and mind you, every defeat is crushing), his reputation as a hamfisted, incompetent tyrant spreads, the exact opposite of the respect he wants to achieve.
The Lyran Commonwealth in BattleTech has an unfortunate history of "social generals" - officers who were promoted not because of actual leadership ability, but because of personal wealth and connections. Naturally, these don't always make the best strategists or tacticians.
Clan Ice Hellion is infamous for their tactics which can be summarized as Attack! Attack! Attack!. Their commanders favor speed over everything else, as such they field light and medium mechs, against opponents who like fielding larger and more heavily armed Omnimechs. The worse example is Khan Raina Montose, who led the disastrous invasion on Clan Jade Falcons occupation zone, which resulted in the Clans destruction.
In any strategy game, real time, or turn based, you can be this trope in at any time! An AI player on Easy or below also normally counts.
In most games, hard or very hard AI opponent isn't much smarter. Best of their capabilities is sending wave after wave to be slaughtered. Thus, such games are likely to have their AI compensate with subtle and/or flagrant cheating. But even if you are winning skirmishes with very hard AI opponent easily, your first match with a capable human opponent can end as devastating curb stomp who thinks of things the AI never would.
General RAAM in Gears of War. No matter how many Locust are currently active on the planet of Sera, you will only ever face 4-men squads. "General, our 4-man squads are being decimated! What should we do?!" "...Send another 4-man squad."
Delta Squad is constantly on the move in-game, and whenever they reach a location where they have to stop or delay for any length of time, the Locust start sending much larger numbers of troops after them. It seems more consistent with Delta Squad constantly encountering roving hunting patrols searching for them instead of fighting an entire army.
The Queen seems to have taken a hint in Gears of War 2, which sends waves of drones at you.
This trope is completely averted in the RAAM's Shadow DLC for Gears 3. RAAM's forces quickly overwhelm Illima and he deploys Brumaks to attack evacuation convoys as well as ordering his sniper teams to take position up on top of buildings where you can't flush them out with grenades. Furthermore, he leads an elite strike team personally in what is probably the most fun mission in the series.
Winston Payne of the Ace Attorney series: despite being apparently one of the relatively higher ups in the setting's prosecutor office, his main job is to show up and lose quickly to the player at the beginning of each game. The fact that Phoenix initially seems to have lost a case to him in the third case of Trials and Tribulations is taken by all involved as evidence that something fishy is going on namely someone impersonating Phoenix attempting to intentionally lose.
Heavily lampshaded, as no one takes Winston seriously in the AA-verse; he's still called "the Rookie Killer" out of respect for what he used to be, but everyone acknowledges he isn't nearly up to that par anymore. On that note, it should be noted that he's only called "Rookie Killer" by people who actually remember him. Both Phoenix Wright and Miles Edgeworth have demonstrated a complete ignorance of who he is, at times. Miles even mistook him for someone on the cleaning staff.
Senator Valtome, Duke of Culbert in Fire Emblem: Radiant Dawn. His first act as general of Tellius' largest and most powerful army? Sending troops to a horrible, fiery death in an attempt to search for the enemy's corpses.
Prince Thrakhath of the Wing Commander series, especially in the Expanded Universe. Every single master plan he's made for the defeat of the Confederation has ultimately failed (many through the interference of Geoffrey Tolwyn), and if it weren't for the fact that he's the Emperor's designated heir, he would have been assassinated long ago. It is thought by many Kilrathi (in private, if they want to keep their heads) that it's Thrakhath's obsession with the humans that's driving the war, to the net detriment of their society, especially since the real purpose is to prepare them to face an even greater threat from deeper in the galaxy. Thrakhath's failure ultimately leads to the destruction of Kilrah and the utter defeat of the Empire.
To his credit, Thrakhath did have major victories between games, and on fronts where the hero wasn't flying. His father, who was the commander of the fleet that destroyed the Goddard colony in Secret Missions, is another example, seeing as his career ended with You Have Failed Me.
Played pretty straight in X-COM: UFO Defense. Having a Good Bad Bug that reset the game to "easy" didn't help of course, but once you've flown to Cydonia and gunned your way through, the Big Bad turns out to be a giant brain which supposedly controls the aliens, but does absolutely nothing in game terms. It will sit there doing nothing until you shoot it dead.
The game also has a hidden script in UFO missions that have all aliens go on the offensive around turn 20. Knowing that, you can clear out all aliens outside the UFO and then place a firing squad in front of the entrance and wait for the aliens to rush out, throwing a smoke grenade for good measure to prevent the aliens from getting the first shot.
Medal of Honor has a rare good guy example in the reboot, in the form of General Flagg, who micromanages the operation via a teleconference while wearing a business suit.
Sanan generals Ku-Embra and Ku-Tsung in Golden Sun: Dark Dawn. They're deadly in combat, but poor strategists; when the protagonists arrive, their soldiers are all milling around aimlessly rather than engaging in anything productive, and the protagonists realize that as long as the generals don't specifically give them new orders, that's all they'll do.
General Duke of StarCraft, who has the misfortune of regularly being on the opposing side of whichever army you're playing through virtually the entire run of the game and its expansion. As a result, in game he wins precisely one battle; over Tarsonis, a planet whose defenses he already knows inside and out. Other then that, he gets spanked by Raynor's Raiders in their escape from the Dominion, he gets thrashed by the Zerg on Char, he gets a fleet vaporized by the Protoss under Tassadar, he gets another fleet wiped out by the UED, he gets thrashed by the UED once more on Korhal, and at last Kerrigan mercifully wipes him and his men out in a surprise attack after the UED have been driven off Korhal again. Suffice to say, his track record after joining forces with Mengsk was a bit spotty.
All the while, Duke is saying that his Alpha Squadron is far better than all the other Confederate squadrons. Doesn't say much about the Confederate military if that's true. Then again, the novels heavily imply that Duke only got his post thanks to him being from the Old Families.
He got yet another fleet and army destroyed in the novel Shadow of the Xel'Naga due to a combination of being the third side in a Mêlée à Trois with a zerg brood and a protoss battle group, and then trying to nuke the Xel'Naga temple they were all fighting over. The nuke woke up the Energy Being inside it, which ate the protoss and zerg and blasted the rest of his ships out of its way as it left the planet.
Similarly, Horace Warfield in StarCraft II doesn't ever seem to be able to accomplish anything except get shot down. Eventually, he joins the ground war and lets the player do the commanding, though in Starcraft II he's defended the Dominion against the zerg and has led no less than five counterattacks against them.
In Fallout: New Vegas, we have General Lee Oliver, or "General Wait-And-See" as many of his troops call him. According to Boone, he received his position via nepotism. His strategy (or "Tunnel Vision" as Mr. House calls it) to defend Hoover Dam from Caesar's Legion consists of one glorious slaughterhouse on the dam, in an effort to overshadow Ranger Chief Hanlon's more tactically nuanced defense of the dam four years earlier. This means his only tactic is to mass troops on the Dam, leaving other territories and bases deeply undermanned and open to the Legion's attacks.
Funnily enough, it's possible to use Oliver's incompetence to your own advantage against Legate Lanius (who despite his reputation is actually a competent tactician). With a high enough speech, you can convince Lanius that the NCR is setting a trap for him. Thinking that this is probably the reason that he managed to get dug in this deep (and considering that's how Graham lost the previous battle), he'll decide to retreat rather than facing a potential defeat.
In the backstory, Joshua Graham was stated to be neither tactically flexible nor strategically brilliant, though he was a terrifying General Ripper and a deadly warrior who went up primarily against tribals and raiders. When up against actual tacticians like Hanlon however he ends up charging his army into a Defensive Feint Trap.
Father Elijah, the former Elder of the Mojave chapter of the Brotherhood of Steel ordered his chapter to hold a power plant against the NCR, despite being vastly outnumbered simply for the sole purpose of trying to find a hidden superweapon of some sorts. In his case, it's a mix of tactical incompetence and complete and utter disregard for the lives of his men when it comes to obtaining old world tech.
When he still had an army, Kratos from the God of War series. His primary method of spreading the glory of Sparta is by slaughtering cities, and ended up nearly dying and losing most of that army because he faced off against a numerically superior foe in open terrain, which is especially ironic given the primary source of Spartan combat fame. How does he save the day? Selling his soul to Ares and letting the actual god of war win the fight for him.
Vice-Admiral Arthur Norbank in Nexus: The Jupiter Incident. The guy is a smug jerk who constantly puts you down as an amateur despite your numerous victories against the Gorgs, while he constantly experiences spectacular failures that result in many of experienced men dying. He constantly disregards intel gathered by agents (especially Ghosts) and then blames them when things turn sour. The guy's most famous victory against the Gorgs was mostly due to the element of surprise, as the Gorgs were expecting to fight the Vardrags and have never even seen a human before. Despite losing his flagship many times, Norbank always seems to survive. Luckily, in one of a later missions, you have the option of not saving him from a derelict ship without being penalized in any way.
Tazar in Last Scenario is an unpleasant combination of this and Armchair Military. It's eventually lampshaded that he never wins a battle, and the closest he comes to a dignified loss is by switching sides to the enemy.
The High Prophet of Regret from Halo is a particularly good example of this, though some of this comes from him being continually outmatched by his colleague the High Prophet of Truth. To a lesser degree, the Expanded Universe shows that the Prophets as a whole often tend to impede the operations of the Covenant due to their politicking, their tendency to meddle in military affairs, and their religious edicts discouraging intellectual and scientific curiosity. Hell, humanity would have never won if it hadn't been for Truth's overly hasty last-minute betrayal of the Elites.
In Halo 4, Captain Del Rio is presented as one, with Cortana and the Master Chief repeatedly questioning his tactical decisions, starting even before they meet the guy. When the Chief straight-up ignores Del Rio's orders right to his face, the entire bridge crew ignores their captain's orders to arrest him. As an added insult, when the Infinity makes it back to Earth he ends up being gulaged by Command (knowing ONI, maybe literally) for picking a fight with a war hero and letting the Didact reach Earth.
The mobile game Great Little War Game and its sequel Great Big War Game prominently feature Generalissimo, your superior. A typical Glory Seeker, as long as it's not his own life on the line. The campaign starts with him ordering you to invade a nearby nation because he wants a war. Naturally, you are the one who does all the commanding. Generalissimo's stupid decisions are the setup for our difficulties. Several times you have to keep Generalissimo alive. The sequel ups his status as this trope by him promoting an attractive woman to the rank of captain, even though it's clear she has no idea what command is. Several missions consist of surviving until you collect a certain amount of money, so that Generalissimo can buy a super-expensive gift for her (e.g. a diamond-studded bulletproof vest). Given the nature of the game, all of this is Played for Laughs.
It's possible to have this sort of Admiral in Sword of the Stars II: Poor stats combine with a negative trait to disadvantage any fleet (s)he leads.
General Vladimir in Command & Conquer: Red Alert 2, the incompetent glory hound who's your superior in the first half of the Soviet campaign. He gets you into trouble in the second mission by assaulting the vastly superior American fleet with only his personal command ship, and then leaving you to deal with them as he flees the battle. Then when you have completed the destruction of the U.S. East Coast fleet, he takes credit for your accomplishments by returning to Moscow before you can. His one saving grace is being savvy enough to see through Yuri, but it feels rewarding when you finally remove him from command.
On the Imperial side of things, the Emperor is entirely too focused on his bushido traditions and code and seems entirely unaware of how much his military success relies on his son, who is more supportive of the Empire's super-high-tech R&D division. The Emperor also gravely underestimates how treacherous the Allies and Soviets can be. However, unusually, he realizes how unsuited his methods are and eventually reconciles with his son, allowing the younger man to lead the Empire to victory.
Applies to The Salvation War during the Curbstomp War of 2008; there's several cases of daemon generals who just don't get it. It doesn't help that the human militaries are actively attempting to deny them, but their mistakes compound the inevitable and turn mere defeats or could-have-been-surrenders into massacres.
Captain, who leads the titular pirates of Lego Pirate Misadventures either botches everything on his first attempt, or will momentarily succeed, only to have everything go bad again. This applies double if whatever he's attempting is in any way nautical, such as when he got lost at sea for two years because he failed to notice his compass was malfunctioning.
Kismet, leader of the Vindicators in the Whateley Universe. Despite the personnel on the team, she consistently gets bad results because no one on the team wants to (or can) work with her, and her plans stink. The one time she managed to get herself blasted unconscious at the start of the simulation, her teammates came up with a new plan, executed it flawlessly, and won.
In Justice League Unlimited, Gorilla Grodd takes control of the rag-tag band of villains who've organized themselves. They commit daring crimes under his leadership, to support his ultimate plan... which turns out to be turning the entire population of the world into apes. Lex Luthor's response is to shoot him. After Luthor is given the Klingon Promotion, Sinestro sarcastically suggests to Luthor that he should make the world go bald for their next evil scheme. This is a Shout-Out to the Silver Age, where comic book villains were fond of grandiose, nonsensical schemes for altering the world to their liking. Grodd was portrayed as a competent leader, except for the whole "turn the world into apes" thing.
Of course, Luthor then turns around and nearly runs the Secret Society into the ground with high membership fees, constant insults to his colleagues, and an even-crazier mad scheme which would ultimately make Luthor into God while giving the rest of them nothing, save enough goodwill for him to allow their continued existence. Understandably, most of the Society rebel... only to learn that this was Luthor's plan all along, to weed out the traitors in his ranks before implementing the final phase.
Lampshaded in Care Bears: Adventures in Care-A-Lot, in which Grizzle's own robot assistant UR-2 informs him that his frequent failures are mainly his own fault (considering that Grizzle frequently "talks" to an inanimate "robot" named Mr. Beaks, it's not hard to see why).
Megatron in Transformers Generation 1. To be fair, he was often also Surrounded by Idiots, but we're talking about a bad guy who was once defeated by a can of spray paint. And then there's his willingness to keep Starscream around, even though not only was Starscream a traitor but an idiot as well. This is lampshaded in the Marvel Comics version where after Starscream pulls the inevitable backstab. Megatron asks himself why he brought Starscream back to life:
"Why? That's what they all asked me. Why him... why Starscream? Why, of all Decepticons, did I decide to revitalize the one whose record of deceit and betrayal is legend? Because I'm an idiot, that's why!"
Futurama has this trope's poster boy: Zapp Brannigan. He's not evil, per se; but he's usually against the protagonists due to his own total incompetence. His deeds have included fighting the Killbots by sacrificing millions of soldiers until the Killbots reached their limit and shut down, attacking the Hubble Space Telescope (in fairness, it did have a defense capability), ordering his ships to make a run so as to clog the enemy ship weapons with their own wreckage, getting his ship sliced in half by flying through a giant windmill despite being told what would happen, destroying an entire repair station due to impatience, destroying the brand new headquarters of The Federation by using his ships' laser at full power to cut the inauguration ribbon, attacking a strategically unimportant planet for no reason and wasting the element of surprise by dumping his soldiers out through the ship's floor, getting enough women killed through fraternization that the army banned them from his command, trying to get the protagonists arrested multiple times, and being taken out in the first second of Bender's Big Score's final battle. He has won offscreen victories (against the Pacifists of the Gandhi Nebula, for instance), and taken credit for other people's deeds, however, so he keeps his job, and is even well-regarded by many.
Brannigan's best moment is when he gives all of earth's defense codes to an enemy lobster alien named "Hugh Mann" who disguised himself as a human by wearing oven mitts.
Zapp Brannigan: Hugh Mann! Now that's a name I can trust!
And of course, this is all before getting into the fact that Brannigan is a sex-obsessed Jerkass who will do just about anything it takes to manipulate a woman into sleeping with him, and then afterwards treat her like she's madly in love with him, when in reality the only two times he's willingly gotten a woman into bed involved pity sex and taking advantage of a new widow.
Leela: For a split second, my reason was overwhelmed by pity.
Zapp: A split second is all it takes.
His list of humiliating defeats now includes an army of stone age neanderthals, led by Fry no less. Though to be fair they had woolly mammoth cavalry and a saber-toothed cat-apault. Technically it's actually one of his greatest on-screen successes, since thanks to circumstances that had nothing to do with Zapp, they agreed a truce on favourable terms:
Zapp: So be it! In recognition of your overwhelming victory, we'll call it a draw!
Getting beaten up by a teenager, despite being a master firebender, and his opponent still struggling with the basics.
Successfully capturing the Avatar, (read, got an elite group of marksmen to do it while he stayed behind), then placing him under a token guard, (read, two guys), and gathering the rest of the garrison together so he can make a speech to them.
Setting fire to his own boat because a twelve year old was making fun of him.
Killing the freaking moon, thereby dooming all of humanity, including himself.
As clarification, the destruction of the Moon imbalances the Ocean's Tide, which is personified as Carpzilla, destroying everything in it's path.
Invader Zim has only one soldier under his command - Zim himself - but his plans and general behaviour are bang on target with this trope. The one time he was ever given command of anything, he managed to halt an entire galactic invasion single-handed by going on a rampage in a gigantic robot without realising he hadn't left his home planet. Lampshaded mercilessly all the time (Zim's ego just won't let him acknowledge it), but of particular note is the episode when he manages to get GIR to stay in Duty Mode. GIR becomes competent enough to realise the primary obstacle to Zim conquering Earth is Zim himself, and subsequently tries to kill him so GIR can do it properly:
The Start of Darknessunaired episode shows that Zim wasn't even put in charge of that robot, having been initially confined to a circle by his leaders, escaping and later hijacking the thing.
The episode Hobo-13 shows that if put in the command of a group of soldiers Zim will needlessly sacrifice everyone until he alone succeeds, using them as either bridges to cross a gap (when there's a tree nearby to knock down), using others as bait and even using his last remaining soldier as a battering ram. Needless to say, the Drill Sergeant failed him so hard he got bruises.
Sidorak in BIONICLE 3: Web of Shadows is depicted as a barely capable oaf who can't even hit a target that's bigger than he is, doesn't like to (more likely can't) fight, and is easily manipulated by Roodaka. In the books, he is actually a pretty decent leader, and his only fault is that he spends too much time on the battlefield. Unfortunately, the writers picked up his negative portrayal, and now Word of God claims he actually was a weakling who had cheated his way to glory.
Exo Squad has Captain Marcus. All of his tactics mostly involve attacking right away with no thought of any battleplans what so ever. Most of which end in spectacular failure.
Also his complete disregard for the use of Exo-Frames in any form. This is especially telling considering the show is about a squad of E-frame pilots.