Alternatively, am I approaching this from the wrong direction, and need to have the Empire represent legitimate antagonistic force?

You've got plenty of answers here so I'll offer a different approach.

The "real" tension in the story, and where most of the conflict will arise, is between the rebel leaders themselves.

Develop the Anti-Team first

I think you should focus on subverting the Team Trope before you make a decision about the Evil Empire trope.

What is an Anti-Team? Rather than heroes learning to work together and synergizing through their strengths to defeat the big bad, you have competitive egos trying to occupy the same leadership roles, not listening to each other, and making selfish mistakes. How does that get resolved? Does it resolve?

I've looked for "anti-team" stories (for my own use) and haven't found many satisfying examples.

• Mystery Men starts off anti-team. They are all jealous and hyper-critical of each other's hero personas. They become the rag-tag team of misfits by the end. By overcoming their anti-team tendencies they become true heroes.
• Guardians of the Galaxy is a team of anti-heroes – each individual has anti-social traits but there's no question they are a team, just dysfunctional.
• Farscape combines anti-heroes with anti-team – the show suffers from lack of focus (bordering on experimental theater). Everyone is equally unlikeable. There is no heart. "Heart" is an archetype on the team – usually the girl – who de-fuses interpersonal conflicts and holds the team together with niceness. I'm not sure if this is a flaw with anti-team or a flaw of Farscape.
• The Last Jedi shows traditional heroes fail because they are anti-team. They leave on personal wild goose chases, they mutiny against their superiors, they misjudge their enemies (and friends), they are over-confident, and when facing loss they make empty gestures of self-sacrifice.

Some other examples come close but don't quite fit. Watchmen is a broken team (arguably not even a team, more like damaged alumni). Star Trek's mirror universe would presumably function as anti-team but it exists for narrative counterpoint. Mirror universe doesn't make sense but neither do the Sith.

Which brings us to...

Rebel against what?

With a fractious and uncertain Anti-Team carrying most of the drama and interest, ditch the cartoon villains. Assuming you have shades of grey and moral ambiguities within the good guys, you don't need a vantablack counterpoint because your team isn't milk white – you can still use the antagonist to counterpoint something – there has to be a pretext for the anti-team to come together. But if their enemy is satanic skullspiders wearing swastika helmets and their plan is to murder the universe, the anti-team are always going to have congruent strategies. Moreover, why are they the only ones rebelling if everyone routinely gets steamrolled?

Empires are not just marching boots they are also economies and cultures. This is the issue I have with Star Wars. A "flat" antagonist isn't doing you any narrative favors, there's nothing to divide your team. That's why I say work out the dynamics of the anti-team first. Figure out what you want to say with that dynamic because the antagonist will be the thing that makes it worse, and succeeds in counterpoint.

Trope Talk does a good breakdown of problems with Evil Empires, as related to goals of the protagonist (ie: replace the Emperor). https://www.youtube.com/watch?v=FCBIXgYCds4

Consider real life rebellions.

If the rebellion is religious, like an English King abolishes the Catholic church and then dies leaving his daughters to sort it out, your rebels might have history with Rome, or prefer a weak local church that can be bribed. They don't all need to be devout crusaders against a cartoon monotrope, some interests overlap but some don't. The US South rebelled so they could keep their colonial economy and lifestyle, but the clock was ticking as they'd lost power in Congress. Meanwhile there were Confederate states that didn't export cotton, and some Union states had race riots. The conflict can still be about a broad thing, but leave room for fractures to occur where some rebels aren't invested in every aspect of the cause.

the Anti-Evil Empire

To break the trope of the Evil Empire, I suggest:

• There is no Evil Empire Don Quixote is a bizarre comedy about a man who is rebelling against the loss of chivalry (or something). He misidentifies his targets, mistakes locals for his enemies, and is a general crazy nuisance. He attacks windmills believing they are monsters. Terry Guiliam's Brazil can be interpreted similarly where the "attacks" are provoked by bucking the system.
• The Empire isn't Evil and is actually very disappointed that you would feel that way considering everything it's done to ensure universal happiness. (Brave New World, Fahrenheit 451)
• The Empire didn't know it was evil but now that you have uncovered this dark secret you will be eliminated.
• The Empire is Evil but (fill in the blank)

posted about 6 years ago

CC BY-SA 3.0

wetcircuit‭

523 reputation 24 58 96 0

Guerrilla warfare

The key to winning an rebellion is surprise. The rebels must appear out of nowhere, attack before the defenders can get organized and leave before reinforcements arrive.

This is standard guerrilla tactics, and is very hard to defend against. Even otherwise competent empires can struggle. The empire's basic dilemma is that they need to defend everywhere, while the rebels only have to attack in one place. Suddenly there are a thousand rebels facing a dozen guards. The guards will fail without having to be incompetent.

Transports are good guerrilla targets. Transports of food, money and arms are all better off in the hands of the rebels than the empire, don't you think?

Of course, the empire know this and will guard the transports. But there are many transports and the roads are long. The guards will get bored and the ambush happens where and when they least expect it.

To make it work, the rebels need spies. They need to know guard numbers, transport schedules and so on. If citizens are mostly in favour of the rebels, this will be easy.

One point of conflict between rebel leaders will be sharing this information.

Unfortunately, guerrilla warfare is only the start, to actually win, the rebels need to take and hold territory. This is much harder. The rebels should weaken the empire a lot before starting this.

Another point of conflict will be when to start the open war.

Some of the rebels will basically be bandits, in it for the loot. Others will be trying to free the oppressed people from tyranny. These groups are not going to like each other.

posted about 6 years ago

CC BY-SA 3.0

Stig Hemmer‭

35 reputation 0 6 7 0

There are already many ways of how a "Stupid Empire" could react or manifest and how the rebels could exploit that.
So I would like to add a few tools of how to SHOW and EXPLAIN the stupidity, so that the reader can understand and relate to that fact. This way you can better avoid unfulfilling "Ex-Machina" feelings.
Just pick what matches your story best.

1. Have a competent but underpowered imperial Officer
   He knows about what goes wrong and why. But he has not enough power to make much of a difference. He could be the main antagonist and the "face" of the Empire (to your readers that is) and either argues with his superiors or can even be too afraid to do that.
   Bonus point: If the rebel infighting gets too destructive and you need to ease imperial pressure, you can just kill him off (being sent to an unholdable position for example). Or you make him more powerful (getting promoted) if you need a real bossfight at the end.
   
   
2. Have a very overconfident and very powerful imperial Officer
   You can also do the opposite of the above. Having one or two severly flawed but powerful characters in the empire could help you show that much of the stupidity is not in fact systemic but rather personal.
   This is not mutually exclusive to 1.
   
   
3. Have a mole (or multiple)
   If the rebels can deliver false intelligence to the Empire, it will be clear, why they make wrong decisions all the time. Just make it clear to the reader that there is a very effective mole. (But don't overuse this. A mole's info can't deviate too far from the truth or he will be found out).
   Bonus point: If you need to crank up the pressure, let the mole be found and imperial decisions suddenly get better.
   (Just a little addition: It could be kinda hilarious if every rebel fraction has their own moles but they are too paranoid to tell each other. In the end they find out that they already had control over most of the imperial command structure but never knew... and now the emperor caught all of them.)
   
   
4. Have strong propaganda
   If your Empire broadcasts a strong message of "We are invincible", even imperial officers will believe that and underestimate the threat of an actual rebellion. But only showing the propaganda itself will not do. You need to make clear that the Empires decisions are based on propaganda beliefs.
   Bonus point: With time and experience the officers will learn to be more cautious or aggressive. So you can again crank the pressure up over time.
   Or make leading officers get more and more demoralized if you wish. (The thought of everyone - rebels AND empire spiralling into chaos is quite intriguing I think).
   
   
5. Have a knowledgebal informant in your rebellion
   Having someone like an imperial Ex-Officer who can explain how the Empire reacts is a good way of making mistakes relatable. Just make him an important part of planning or briefings.
   Or have him explain things to inexperienced rebel grunts who scoff at the empires stupidity.
   
   
6. Have an outside viewer
   Someone like a traveler or a normal civilian, having to flee because rebels took his hometown for example, is a good tool to show how the Empire reacts and how their priorities are set (and how the rebels themselves are perceived by the population).
   He could either get to a refugee camp or just flee across the country.
   To spice this up you could make him a rebellion-deserter who really has reasons to run from the rebels.
   
   
7. Have good - maybe honorful - reasons for wrong priorities
   How about an Empire that makes an effort to protect civilians? But they constantly underestimate the trouble of managing refugee camps and evacuations (and yes the Empire can be evil and still care about its workforce. No one said they would provide good care in these camps... just some protection. Eg: If I want to get more gold in the future, I need some gold miners).
   A brawl in a refugee camp for example might very well throw them off guard. The rebels could even abuse this tactic to lower the empires ability to react.
   Or they are very cautious and really don't want to battle unprepared so they wait just a little too long for supplies.

posted about 6 years ago

CC BY-SA 3.0

SRMM‭

5 reputation 0 1 1 0

Well, remember, many totalitarian regimes are in fact woefully inefficient. Largely because the emperor/fuhrer/first citizen needs to make sure the people beneath him are either not ambitious enough or competent enough to potentially overthrow them. The emperor has to be a paranoid backstabber to maintain a totalitarian regime, and he thus assumes everyone else is a paranoid backstabber. Hence members of his cabinet are constantly rotating, no united vision can get done, the empire needs multiple spy organisations that are all spying on each other and murdering each other, et cetera, et cetera.

Basically, an incompetent totalitarian regime shouldn't be hard to write; real-life totalitarian regimes tend to be woefully incompetent as is.

posted about 6 years ago

CC BY-SA 3.0

Matthew Dave‭

255 reputation 7 33 48 0

Talented individuals can be seen as dangerous to totalitarian regimes. Stalin executed many very capable generals and when the crisis came, talented, experienced officers were in short supply and rather nervous.

Removing potential threats and rivals could possibly thin out the acknowledged talent within the regime. Some of your brilliant minds were smart enough to not push the fact of their intelligence - the smartest one in the room needs to be smart enough to let someone with more power think themselves more intelligent.

If the regime you envision is pulling in different directions simultaneously, they destroy themselves and one of the brilliant minds would realize this and recommend that a single plan with contingency plans be adopted and followed to defeat the threat.

People will quarrel and pull in opposite directions, sabotage each other and do all manner of self destructive things, but give them a common foe and that falls aside. Defeat of the rebellion is more important than egos and rivals can be disposed of later - that is what peace is for - politics.

What you have are talented theorists who never had the opportunity to actually see their plans in action with no resistance to the regime. Their predecessor probably retired as did his, the last one to have seen ‘active service’ might have told stories to his heirs before dying of old age.

They must agree on defeating the revolution, methods might differ but various theories would be employed, some might be rather odd, the brainchild of the guy who graduated last in his class.

Surprise or disbelief could lead to early errors, but those would diminish as the more intelligent among them discuss strategy and let the others know ‘adults are talking - be quiet kids’ while they figure a way to crush the rebels.

The regime has the advantage of numbers, intel, discipline and training. The rebels must be more motivated and mobile as they will rely on blending in with the population and being as hard to identify as possible lest they be captured and end up being executed in a rather graphic way.

posted about 6 years ago

CC BY-SA 3.0

Rasdashan‭

520 reputation 25 59 93 0

People can be intelligent and competent yet still unable to do their job. The military might be underfunded (seems really unlikely but you can set your story up however you like). You might be the best commander in history but you are going to fail if your equipment and personnel are not at the levels that they should be.

Or maybe people get promoted in this inactive military for political reasons. Usually a higher ranking soldier gets that way due to experience and training. But if there is no chance at experience and the training is okay but done by people who also lack that experience, coming through the ranks doesn't equal competence at your job.

If the Empire has money though, look for a lot of these problems to be fixed pretty quickly. You can't improve infrastructure overnight, and distributing tech and getting personnel up to speed will take time too. But staffing levels and training are going to go way up in weeks after the first attack or two.

posted about 6 years ago

CC BY-SA 4.0

Cyn‭

1130 reputation 25 439 215 0

I don't think "mind boggling" stupidity will be plausible, otherwise, why weren't they overthrown decades ago? Just because nobody thought of it? That's not a good enough reason for an oppressive regime that rules a large number of people; there is always some percentage of any country that hates the government (even our own here in the USA).

What a totalitarian regime can be is mind-bogglingly wasteful of gold and lives, and mind-bogglingly cruel to dissenters and even innocents they think are dissenters. They can be mind-bogglingly adamant on religious adherence, even if the leaders themselves are not and partake of drugs, sexual orgies, liquor, and rock-and-roll with abandon -- religion keeps the subjects in check and gives them something to worry about. A totalitarian regime, even if not very competent in actual battle, is typically very good at the psychopathy of scaring the shit out of their subjects to keep them in line.

Due to that fright, your rebels may find themselves unable to trust anyone, betrayed by the very citizens they are trying to free, informed upon, spied upon, and in real danger because if they are caught, they are publicly and slowly skinned alive and tortured to create the maximum screaming pain possible, just as an example. And don't think most of the citizens will be outraged by this, most of them will be cowed.

I would make your antagonists (like the British fighting the American Colonists) not exactly incompetent, but wasteful of men, stuck in traditional battle, and unable to adapt to guerrilla tactics, hit-and-run ambush (i.e. the rebels kill a few and then run like hell), subterfuge (roadside bombs / traps, or similar lethal traps in woods), supply line disruption, and so on.

I would not make this fight between competent fighters and incompetent fighters; I would make between highly intelligent fighters and normally competent fighters. The regime doesn't stumble. The rebels keep outsmarting them.

Because the rebel leaders are smart, and to them the regime is predictable, and anything predictable can be exploited.

posted about 6 years ago

CC BY-SA 4.0

Amadeus‭

3156 reputation 2 1399 613 37