Summary: How can you miss what you've never had?
Author's Note: I think this is pretty self-explanatory.
Disclaimer: I don't own Star Wars.
Despite not having been born on Tatooine, when the Jedi come Tatooine and slavery is all Anakin knows. He has been in bondage for literally as long as he can remember, the entirety of his life. Though Anakin often dreams of freedom, of a live away from the Hutts where the word "slave" is just a word and not a reality, he can not begin to imagine what it must be like to live free.
When the Jedi come, Qui-Gon Jinn wins Anakin and liberates him from slavery. He is taken to Coruscant and after Naboo itself is liberated from the Trade Federation, Anakin becomes a Jedi.
And, thirteen years later, Anakin finds himself signing his body and soul back over into bondage, when he kneels before a disfigured Lord of the Sith and accepts the name Darth Vader.
What he finds odd afterwards, after he becomes Vader and discovers what it is like to serve under his new Master, is that he doesn't miss the freedom he had before he became a Sith.
And what Vader discovers is that he was never free to begin with. Even when he was no longer a slave under Watto, he never allowed himself to be free.
All of the peace that Anakin Skywalker might have found if he had let go of the memories that had accumulated during his life on Tatooine had been squandered, because instead of letting go Anakin clutched those memories close to his chest and allowed them to poison everything around him. He allowed himself to be corroded, to be corrupted by his old resentments and fears.
Anakin Skywalker's possessiveness of his wife had bound him to fear and suspicion. Padmé had always been blameless, always been true to him, but he had refused to believe it and drove her to fear of him, wariness of him. Their marriage, founded on love instead became a bed of uncertainty and shame.
And, had Anakin Skywalker just trusted his Jedi Master, everything might have turned out different from how it did.
But Darth Vader does not focus on the past. Darth Vader knows that the past is immutable, and can not be changed.
And he finds it deeply ironic that, now that he is "liberated" from the Jedi's "tyranny", he is more a slave than he ever was as a child on Tatooine, before the Jedi came.