When you examine not only what Lando did but why, it’s clear that at every step of the way he had Han’s interests at heart, even at great risk to himself, the life he had built for himself on Cloud City, and the people that depended on him.
We know that by the time the Millennium Falcon arrived at Cloud City the Empire was already there and a deal had been struck between Darth Vader and Lando. The deal stated that in return for continuing to look the other way at the illegal activities of Cloud City, the crew of the Millennium Falcon would be used as a way to lure Luke Skywalker to Cloud City. The crew itself was not to be turned over to the Empire in this initial deal.
First off, if the Empire showed up at your work, whether you were a legitimate business or not, you’d be scared s***less. Even if you once thought that the Empire wasn’t so bad, I’m sure that by this point, everyone in the galaxy knew about Alderaan. So what is Lando to do when Darth Vader shows up and says he is laying a trap for a stranger you’ve never heard of? Option one is to fight to protect this stranger named Skywalker, sentencing yourself to death along with possibly everyone whose life and livelihood depends on you, the people of Cloud City. Han, Chewbacca, and any other traveling companions on the Millennium Falcon will be warned in this scenario, but at the cost of everyone and everything that you swore to protect.
Option two is to make the best deal you can, where the only casualty is someone you don’t know.
So what would you do? I don’t care how moral or righteous you are, you’d do exactly what Lando did. Lando makes a deal to protect Han Solo and Cloud City. The short term might mean pain, but the deal means life. The cost is some guy named “Luke.”
Lando also takes the time to go down to the holding cell to check on Han and inform him of everything that is going on, as well as to say he is sorry. Lando still takes the risk of upsetting Vader by revealing Vader’s plans. These are not the actions of a scumbag, but rather someone trying to protect a friend. No one from the Millennium Falcon wants to hear it, but Lando has been acting in their best interests the entire time, and he still is.
Of course, you can never trust a Sith, so Vader alters the deal (the first time), saying they are going to test the carbonite freezing he plans to use on Luke by subjecting Han to it first. If the captain survives, Boba Fett will be given Han’s frozen body. Lando is incredulous, but with almost nothing that can be done (because again, the Empire and Darth freaking Vader are there) he does the next best thing he can do for Han—protect the ones he loves. Lando gets an assurance that Leia and Chewbacca will be allowed to remain at Cloud City under Lando’s protection.
If Lando was only trying to protect himself, why would he care about doing that? He cares because Han is his friend, and this is what he can do for him. It’s not ideal, but it’s the best he can offer. In a great moment of peril wouldn’t you want to know the ones you love will be taken care of and safe?
When Vader announces he is altering the deal yet again, Lando realizes he has to act now to protect Han’s friends, even at the peril of Cloud City. If anything, this is his first morally dubious decision. Are Chewbacca and Leia so important that the live of every person on Cloud City is worth the risk of betraying the Empire?
As if we needed further proof that Lando has been acting like a hero this entire time, we see that he already planned for a situation where he would turn on the Empire and Vader. He alerts Lobot (his assistant with a computer attached to his brain) and immediate action is taken to escape with Chewie and Leia in tow. With his very public announcement to the entire city to flee, he makes no attempt to hide his betrayal of Darth Vader, making himself an enemy of the Empire. He writes his own death warrant.
What does he get for this heroic act? He gets choked by a Wookiee, even as he tries to explain Han can still be saved. Oh, and then when flying away he agrees to turn the ship around to save that same stranger Vader wants to find, Luke Skywalker, and that action is based on Leia having a “feeling.” Talk about bravery.
We don’t need to rehash his heroic deeds in
The first time I saw