There's this tweet thread I've been wanting to do for quite a while, but I know it's going to be really long and I just never been able to block out the time for it. Still, everyone is home right now, so it's a good time for a long talk.
Maybe I'll just go ahead and start this now and add to it over how many ever days it takes to complete. I may need the extra time to get thoughts together anyway, as it's quite a big topic and I don't really know how to start.
Anyway, here's the topic:

What exactly was Luke's plan to rescue Han Solo at the beginning of Return of the Jedi?
The more I dive into this, this less sense it makes. I honestly don't even know where to start with it. I guess I'll start with this question:

Did everything go according to plan or not?

However you answer that, it doesn't make sense.
I guess the next question to ask is "Why?"

I mean why not just walk in with lightsaber in hand and go "I'm a Jedi. Gimme Han!"?
I guess we're supposed to accept that Jabba -- who canonically Han stepped on the tail of just for fun -- is way too powerful for that so you have to be extra double sneaky. Convoluted sneaky even.
So where to start with this plan? I guess try to figure what was the opening move. As far as I can tell, the first thing they did was get Lando to pose as a guard for Jabba.
This is the only thing they did that directly makes sense and leaves no questions for me.

It also amounts to absolutely nothing because by the end the only thing Lando did was need to get saved by a blind Han.
So what's next? I guess Chewie disappears to pretend he's been captured by Leia posing as a bounty hunter (C3P0 remarks on how Chewie is missing, and we can assume he wasn't let in on any of the planning).

I don't really get that, but we'll revisit.
Next, Luke puts his newly crafted lightsaber in R2.

Why?

Again, I guess we have to assume that Jabba is just so powerful Luke knows he needs to be extra crafty and only have his weapon available when it will be a surprise.
So now C3P0 and R2 go to deliver a message to Jabba.

This is where it starts to get really confusing, because the message is "Hey, I'll give you these droids for Han."
So, a lot of questions here.

Did Luke think there was a chance Jabba would say, "Oh cool. Great trade. I'll keep the droids. Take Han."?

If that did happen, what then? Now he lost his droids and his lightsaber. Does he have to go back and rescue them?
I mean, I don't see how this part of the plan wasn't anything other than a step backwards. I mean, best case, he now has two droids to rescue from Jabba. What actually happened is now he has Han and the droids to rescue. But he has a crouching Tiger, hidden lightsaber, I guess.
Now comes Leia dressed as a bounty hunter. And it gets even more confusing.
So, Leia hunter really plays the part -- even threaten to blow everyone up if she doesn't get paid enough -- and gives Chewie over to Jabba.

So, if you're keeping track, we've gone from needing to rescue Han to needing to rescue Han, R2, C3P0, and Chewie.
So Leia hunter sneaks in at night to unfreeze Han and rescue him -- in front of everyone. I mean everyone is in the room and she's just assuming they're asleep or drunk or something.

Is she trying to get caught?
Let's say she isn't. Let's say she unfreezes Han and gets him out. Now you've gone from needing to rescue Han to needing to rescue R2, C3P0, and Chewie. Again, a big step backwards.
But if that's if things went to what (presumably) was the plan. Instead, Jabba wasn't drunk or asleep -- can't outsmart that guy.

So now we've gone from needing to rescue frozen Han to needing to rescue blind Han plus R2, C3P0, Chewie, and Leia.
And, of course, this whole time Lando is just standing there, maybe reporting back to Luke.

"Oh no! They're all captured!"

or

"They're all captured... exactly as we planned!"

or

"They're all captured... even the ones we didn't plan to be captured."
So now comes Luke, the Jedi, who tries to Jedi mind trick Jabba into giving him back all his friends.

Which brings the question: Did he think that might actually work? Because, if so, why not open with that?
*hand wave*
"Give me back Han."

seems much simpler than

*hand wave*
"Give me back Han, Leia, Chewie, and R2. Oh yeah, and C3P0, I guess."
Then, if the Jedi thing fails, have his friends implement some sort of backup plan, hopefully using Lando, the only intelligently placed asset.
Of course, it does fail, and Luke is dropped into the rancor pit.

A lot more questions just on that.
I assume Lando is doing something else other than occasionally tilting up his mask so we can see he's Lando... such as sending information back to Luke. Shouldn't he have like warned him about the rancor pit?
Also, unless Jabba got the rancor that day, it's not like he could keep it a secret. People are going to talk about how he keeps dropping people to be eaten by a rancor. I don't think there's some extreme gangster code protecting that secret.
Actually, the more I think about it, how insane is it that they did all this prep and multiple subterfuges but somehow missed knowing about the rancor pit?
And wouldn't this be a great time for that hidden lightsaber? I mean, fighting a giant monster -- wouldn't it be great for that? No? Still want to save that for later?
And maybe this breaks Jedi code, but why not have a second lightsaber? He could have the one hidden in R2 for a later surprise and then another one on him (it's not like anyone searched him for weapons on his way in -- I mean, there's weapons everywhere in that place).
Assuming, though, making a second lightsaber would be too hard to make, why not bring a gun? Or multiple guns? It's not like he's against using them since he used the force to grab a gun as he fell.
Of course, maybe you're of the theory that Luke purposely got himself dropped in the rancor pit as yet another ploy to make Jabba think he's won again and get his guard down.

That's a stupid, stupid plan.
"So, I'll just let Jabba drop be down there unarmed. Now he'll think he's won again like when he captured Leia."

"But then you'll have to fight a giant monster with no weapons."

"Eh... I'll figure something out. You don't want to over plan these things."
So, in summary, we've gone from:

Han is captured by Jabba.

to

EVERYONE is captured by Jabba (except Lando who doesn't really seem to be doing anything).
For the final part, I don't really have any new questions. Luke finally gets his hidden lightsaber and he and friends slaughter everyone. Straightforward enough.

But it brings me back to my first question: Was this the plan working or going horribly wrong?
The thing is, it all looks like it was a series of plans that went wrong, but each of those plans would have caused problems if they worked -- as we've already discussed.
If Jabba had given Han in exchange for the droids, Luke would need to get the droids (and his lightsaber) back.

If Leia had successfully snuck out Han, they'd still need to rescue Chewie.
I can get Luke expecting the droid exchange not to work (and was just a ploy to smuggle in his lightsaber), but it's hard to buy that getting Chewie and Leia captured was all some sort of ploy. Still, the evidence kind of points to that.
If they thought just unfreezing Han and sneaking him out would have worked, they never would have had Leia and Chewie come in to do that. They would have just had Lando do that as he's already right there inside.
And the last failed plan was Luke using the Jedi mind trick. As I said already, if they really thought that might have worked, seems like they would have opened with that.
As dumb as it is, it does seem like Luke purposely got himself thrown into the rancor pit unarmed to flail around and barely not get killed.
As best as I can make sense of things now, what they did was a bunch of plots that they intentionally expected to fail to get Jabba to get his guard down and think he's won.
And they've definitely eliminated any suspicion they have a man on the inside since one would have assumed someone like that would have helped by now. But Lando has wisely done absolutely nothing.
But why? Why this elaborate, convoluted strategy to come at Jabba? Why not just run in and bop him with your lightsaber and walk out with Han? It makes so little sense.
Well, here's how I'm going to finally close out this thread. I'm going to write the missing planning scene from Return of the Jedi, showing exactly why they settled on this plan and finally making sense of it.
*Luke, Leia, Lando, Chewie, and R2 meet in... some back room on Tatooine, I guess*

LEIA: "We have to find a way to rescue Han from Jabba."

CHEWIE: *growls*

R2D2: *affirmative beeping*
LUKE: "I shall use the force to try to determine a way that we can defeat Jabba the Hutt."

*Luke goes into a trance for a few moments*

LANDO: "What did you just do?"
LUKE: "I used the force to go forward in time, to view alternate futures... to see all the possibilities of the coming conflict."

LEIA: "How many did you see?"

LUKE: "14,000,605."

LANDO: "How many did we win?"

LUKE: "One."
LEIA: "Wait, I thought Jabba was just some gangster."

LUKE: "No, he is the smartest, most dangerous being in the galaxy."

LEIA: "But he's like a slug criminal."
LUKE: "He is even more dangerous than the Emperor. And that's why the way to defeat him -- the only way -- is an extremely convoluted plan."
LANDO: "Well, Luke, we've seen your great prowess with the force in adventures that occurred after the last episode but the audience has never seen, so we'll go along with your plan no matter how insane it seems."

CHEWIE: *growls*

R2D2: *affirmative beeping*

LUKE: "Great."
*Luke pulls out a whiteboard*

LUKE: "First thing, Lando, you're going to get yourself inside as one of Jabba's guards."

LANDO: "No problem. I can use my gangster contacts to make that happen. Then what do you want me to do?"

LUKE: "Absolutely nothing."
LANDO: "Huh? I'd be in the inside. Seems like there would be a ton I could do."

LUKE: "Anything you do could raise suspicion. Jabba is just too smart. You must do absolutely nothing until you pilot the skiff on our final escape."

LANDO: "What skiff?"
LUKE: "We're getting ahead of ourselves. So Lando will be inside doing nothing. Next, I want R2 to deliver himself and C3P0 as gifts to Jabba. But first, I'll hide my lightsaber inside R2."

R2D2: *affirmative beeping*
LEIA: "So now your lightsaber is smuggled inside."

LUKE: "Right."
LANDO: "I could also smuggle his lightsaber inside since I'll be a trusted guard."

LUKE: "No. That would be doing something and you're not doing anything. So next, Leia you're going to pose as a bounty hunter and deliver Chewie to Jabba."
CHEWIE: *growls*

LUKE: "I know, but you have to trust me on this." *turns to Leia* "And play hardball with Jabba on the price; get him to respect you as a bounty hunter."

LEIA: "So what will I do now that I've got his trust?"
LUKE: "At night, you're going to secretly free Han from the carbonite."
LANDO: "I could do that since I'll already be there."

LUKE: "What part of 'do nothing' are you having a problem with, Lando?"

LANDO: "But I want to do something!"

LUKE: "How about you shut up; that's something."
LEIA: "Anyway, if I free Han, what happens with Chewie and the droids?"

LUKE: "Don't worry about that, because this won't work. You're going to get captured. We're going to let Jabba think he's winning."

LEIA: "Oh. Okay. But what will happen to us?"
LUKE: "Han and Chewie will get thrown in prison. Knowing Jabba, though, he'll most likely put you in some sort of demeaning slave girl outfit."

LEIA: "A what?"

LANDO: "I want to hear more about this outfit."
LUKE: "Like a metal bikini, probably."

LEIA: "I'm not wearing that!"

LUKE: *rolls eyes* "You'll have to. You've been captured. Keep up. So anyway, now I come, and I try to Jedi mind trick him into releasing everyone."
LEIA: "But that won't work."

LUKE: "No, because Jabba is too powerful. Once again, he'll think he's won and drop me into his rancor pit."

R2D2: *excited beeping*

LUKE: "No, it's not time for my lightsaber yet."
LANDO: "Then how are you going to beat that giant rancor monster of his?"

LUKE: "Um... I dunno. I'll grab a bone or something. Anyway, we'll circle back to that. Let's just go forward saying I somehow beat the rancor. Guess what happens next?"

LEIA: "He shoots you?"
LUKE: "No. He'll be so enraged, he'll want to go out on his sail barge to throw us into the Sarlacc pit."

LEIA: "And you're sure he'll do that and not just shoot us all?"
LUKE: "Like 76% sure. And he'll definitely not shoot you because you'll be in that demeaning slave girl outfit. Don't forget that."

LEIA: "I did not forget the demeaning slave girl outfit."
LUKE: "And now we've done it. We've gotten Jabba out of his palace. He's finally vulnerable."

LEIA: "I'm sorry... why couldn't we just go after him at his palace?"

LUKE: "Because he's too powerful there."

LEIA: "How?"
LUKE: "Because... reasons. He just is, okay? But out on his sail barge, we'll finally be able to take him down. And he'll be vulnerable because he'll think he's won."
LEIA: "From my vantage point in the demeaning slave girl outfit, it kind of looks like he has won. And mean, he's captured all of us."

LANDO: "Not me. Which means now I can--"

LUKE: "Are you about to propose doing something?"

LANDO: "No. Sorry."
LUKE: "Anyway, Leia that's why the plan is so brilliant. Jabba will be absolutely let his guard down. But before we're dropped to the Sarlacc, R2 will finally throw me my lightsaber and we'll all fight back."

CHEWIE: *growls*

R2D2: *excited beeping*
LUKE: "And during all that commotion, that's when you, Leia, are going to take out Jabba."

LEIA: "How?"
LUKE: "By strangling him with your chain. Oh, I forgot to mention that along with the demeaning slave girl outfit, you'll also be chained up."

LEIA: "One would assume. So wait, I thought Jabba was some super mastermind, but in the end I'll just choke him with a chain?"
LUKE: "I used to force to look in the future, and the only thing Jabba is vulnerable to a slave girl chain choking. And it will be easy for you because you'll be so mad."

LEIA: "Because of the demeaning--"

LUKE: "Because of the demeaning slave girl outfit. Yeah, you got it."
LEIA: "And what are you all doing during this?"

LUKE: "Just basic blowing things up and shooting things until we defeat everyone."

LANDO: "I get to help with that, right?"
LUKE: "No. According to future I've seen, you'll struggle a bit with one guy and then fall off the skiff and need Han and Chewie to rescue you."

LANDO: "Why am I even a part of this again?"

LUKE: "To pilot the skiff when we all finally leave together."
LANDO: "Do you even really need me for that? Why can't one of you just pilot the skiff?"

LUKE: "Because we'll be too tuckered out from all the action-adventuring."

LANDO: "Fine. Whatever."
LUKE: "So there's the plan. This is it. This is how we win."

LEIA: "There's really not another way to do this where I don't end up in a metal bikini?"

LUKE: "No."
LEIA: "Another question: If you can see in the future and come up with these convoluted plans, can you use this against the Emperor after we get back Han?"

LUKE: "No."

LEIA: "Why not?"

LUKE: "Um... I don't feel like it."

LEIA: "That's not a good answer."
LUKE: "Um... then... Let's say because of his power in the dark side of the force, it makes the future all cloudy around him. Would you buy that?"

LEIA: "Yeah, I guess that works."
LUKE: "Anyway, there it is: Our plan to rescue Han and defeat Jabba and it all makes sense and there are no plot holes. Are we ready?"
LEIA: "I guess. Kinda feels like I need to tan first."

LANDO: "Still doesn't really seem like you need me, but okay."

CHEWIE: *growls*

R2D2: *affirmative beeping*
*C3P0 walks in*

C3P0: "What are you all up to?"

EVERYONE: "Go away, C3P0! No one likes you!"

CHEWIE: *growls*

R2D2: *negative beeping*

C3P0: "How rude!"
And that's it. That's all I have to say about Luke's plan to free Han in Return of the Jedi... unless I forgot something or have another revelation. Thanks for finally letting me get this off my chest!
Okay, I'm going to add to this thread as some people brought up a possibility I hadn't considered -- because it was stupid (though still worth discussing). That's that they all weren't working in coordination to rescue Han.
Thus Luke and the droids come in with their plan, Chewie and Leia with their plan, and I guess Lando just stands back shaking his head as they're all captured while muttering, "What a bunch of idiots."
The reason I hadn't considered this is it just seems so stupid they wouldn't coordinate. It's established they have interstellar communications; why wouldn't they mention their plans to each other?
Still, let's pretend because interstellar storms or some other handwave they missed telling each other their plans. I'm still not sure this works.
Now, it does look like Lando was at least in cahoots with Luke based on the nod he gives Luke just before Luke gets back his lightsaber, the nod communicating, "I've been doing absolutely nothing just like you told me."
So, I think it's plausible Luke and Lando could have had an independent plan all around sneaking in Luke's lightsaber in R2. Leia and Chewie raise more questions, though, as that does not work by itself.
If this was just Leia own plan working alone, how was she going to get Chewie back? Or was she really so desperate that she actually did capture Chewie (who she never liked) to get Han back with no plan to then rescue the Wookie?
That would explain why, in Force Awakens, Chewie walked right by Leia after Han was killed with no attempt to comfort her. Their relationship was never the same since Tatooine.
Still, that seems really out of character for Leia. Plus, wouldn't it have thrown her off when she saw C3P0 working for Jabba? If she weren't working with Luke, that would have been a surprise.
So, no, I still think the scene I wrote earlier is the only logical explanation for what was Luke's plan to rescue Han in Return of the Jedi.
I did see someone suggest that the official novelization of Return of the Jedi actually explains their plan and what was going on. I highly doubt this, but I will seek it out and report back if I learn anything new.
Okay, I spent $7.99 for the Kindle edition of the official novelization of Return of the Jedi. I am now financially invested in finding answers.
I should mention I had played the SNES video game version of Return of the Jedi, and that offered no insight on this question other that in fact it’s very hard to fight a rancor with a lightsaber and much easier with a blaster.
Also, the easiest way to beat the Emperor is with an Ewok armed with a bow and arrow, but you need a cheat code for that so it’s definitely not canon.
Been busy and I haven't finished the Return of the Jedi novelization yet, but it will definitely be worth an update. I keep thinking it's finally starting to make sense of Luke's plans only to again be disappointed.
Are novelization of movies still a thing? I used to read them as a kid, and the last one I remember reading was The Phantom Menace one back when that movie came out.
The one I most remember was of the movie Gremlins. You learn in the prologue that Gizmo was made by aliens. I also read one of the Teenage Mutant Ninja Turtles movie out of curiosity of how you'd make a movie that was mainly punching ninjas interesting as a book.
Anyway, I will update soon. I feel like the novelization is clarifying a few things at least... while still leaving other things confusing.
Okay, sportsfans, let's jump back into this. I read the novelization of Return of the Jedi (well, the first part about rescuing Han) and it's changed my mind about how Luke's plan had to play out.
First, I want to chastise you all. I was working from memory (I last watched Return of the Jedi a few months ago) and I said Luke was trading the droids for Han. That was wrong. He was giving Jabba the droids in exchange for an audience with Jabba.
I can't believe no one corrected me. Anyways, it doesn't change any of the analysis other than to confirm that whole part was a ploy (obviously, Luke never intended Jabba to keep his droids -- at least not R2).
Anyway, taking the novelization as canon (it was done form the script and by a veteran movie novelizer who also wrote the novelization for Goonies), here are all the facts it clarifies:
Luke's plan was to get Han out of the palace because it was too well guarded (he says this explicitly to Han).
Lando was working with Leia.

Lando was also working with Luke.

By transitive property, I think we can say that Leia and Luke were working together.
Luke, now that he is a full-fledged Jedi can kind of see the future.

I think it's also implied by a line from Jabba's robot that Luke specifically messed with droids on the sail barge to make sure R2 got assigned there.
Leia was surprised when Jabba caught her. That did not seem to be part of the plan.
Luke also seemed surprised by the rancor -- though I really don't get how anyone could miss Jabba has a rancor he tosses people to (especially with a man on the inside). I think we should just let this go, though.
Anyway, I made this conclusion as the novel was written in sort of a wandering third person, constantly switching whose head it was in (something I was told was bad writing early on though I have seen in in early novels).
Anyway, here's what make sense: Luke saw the future and knew he could manipulate things to get Jabba out of his palace and have his lightsaber in R2 at the ready and win.
Here's what doesn't make sense: Leia. What was her part in the plan if she didn't expect to be captured? I guess hand in Chewie, unfreeze and sneak Han out, and somehow have Lando get Chewie out -- which sounds like a bad plan.
Here's the thing: Luke's plan -- the one to get everyone out of the palace on the sail barge -- relied on Han being unfrozen but still in Jabba's possession.
So how do we take all this and make something coherent out of it?

Here's how.

First, a question: What did we learn from the prequels?
We learned that Jedis are jerks.

So, let's circle back to my very first question in this thread: Did everything go according to plan or not?

It went exactly to plan -- _Luke's_ plan.

But he did not share that plan. Certainly not with Leia.
LUKE: "It's a simple plan, Leia. You pretend to be a bounty hunter who captured Chewie to get inside, and then you unfreeze Han and sneak him out. Then Lando gets out Chewie in ensuing commotion."

LEIA: "What if something goes wrong?"
LUKE: "I don't see any reason to even speculate about that or what Jabba might make you wear if that happens."

LEIA: "I have a bad feeling about this."

*Luke puts his hand on Leia's shoulder*

LUKE: "The Force doesn't care about your feelings."
I think that's it. I think that's now the best explanation if you want to try to put together a coherent explanation of the beginning of Return of the Jedi. I think I'll declare this thread closed again unless I encounter any new information that either verifies or disputes this.
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