Choosing just who to write for given a quite literal whole Star Wars universe in which to dip a Geek Couples toe, this may perhaps seem the least obvious such pairing but its ups & downs are the ones which in retrospect drives the entire narrative. Obi-Wan Kenobi made perhaps the only massive error of his long career as a Jedi Master in misjudging the nature of his relationship with his first Padawan, giving him a brother where a father figure might have been of more benefit to a boy who'd left his mother behind & would indeed have to deal with her death. Anakin Skywalker's reaction to which gave the first clue to his eventual fall to the dark side and shedding of his very name in favour of becoming Darth Vader, before love of a different nature redeems him. His role in Jedi prophecy played out in a manner nobody involved in the struggle between Empire & rebels could have foreseen....
It's worth remembering, of course, that at the start of their relationship Kenobi had barely had time to adjust to the transition from Padawan himself to the rank of master, having promised the dying Qui-Gon Jinn that he'll train the boy. Between The Phantom Menace and Attack Of The Clones it becomes clear Kenobi's gone some way towards gaining the wisdom that will see him later take a second Skywalker as his apprentice, perhaps in a sense seeking to rectify the mistakes he made with Luke's dear old dad in the last days of the Republic. Days that were driven by the man Anakin had come to see as a warped sort of father figure pulling the final few strings of his coup - liberty dying to thunderous applause in the Senate.
Indeed, there's probably an argument for saying that Chancellor Palpatine/Darth Sidious' true master-stroke in engineering the Clone Wars is paving the way towards severing the connection between master & apprentice, playing on the younger man's fears knowing that the senior of the two Jedi is away on other business - and therefore unable to intervene - whether that be investigating what will become the Grand Army of the Republic or apprehending General Grievous. For there would surely have been at least some chance that had Obi-Wan been there to offer his counsel, young Anakin wouldn't have been so quick to break the Jedi rule of non-attachment & go falling in love with Senator Amidala, allowing heart to rule head with such terrible consequences for both parties.....
To Kenobi's credit, if any can be given in the aftermath, he is at least quick to realise that he too was played by the recently self-appointed Emperor and as such has been manipulated into ultimately failing in his duty as master to the soon to be suited up Vader, the man he rescues during the mission to save the Chancellor from the clutches of the Separatists unable to return the favour. Tellingly it's also Obi-Wan who's given the task of informing his young charge that the Jedi Council wants him to spy on Palpatine, rightly dubious given the sudden increase in his sway over political matters as the Clone Wars rage on.
The use of that power and his motives for doing so serve to drive yet another wedge between the spiritual “ brothers”. Anakin is unwilling to do it and has unwavering belief that the Chancellor is simply a concerned public servant looking out for those he was originally elected to represent, whereas Obi-Wan sides with those who refuse to grant Skywalker a position as Master despite giving him a seat on their Council at the behest of the man who will be Emperor. All of this is but another stab in the back unknowingly delivered by a master in danger of losing more than just a planet but unable to react until it's far too late. Leading to younglings, of the sort whose class Anakin interrupts while looking for Kamino, becoming the innocent victims of Vader's first act. Now the right hand of the newly born Empire after his assault on the Jedi Temple, the moment saw any good left in Anakin die, and was witnessed only second hand by the man whose later exile to Tatooine could be seen as an act of penance for his all too apparent neglect.
Indeed, if we read a little deeper into Obi-Wan's interpretation of those events as told to Luke, what he reports of those days does make sense even if it's clouded in metaphor.
“A young Jedi named Darth Vader, who was a pupil of mine until he turned to evil, helped the Empire hunt down and destroy the Jedi Knights. He betrayed and murdered your father.”Replace that final he with the arrogance that helped turn him more machine than man, which old Ben was never there to counsel against at its worst, and it becomes clear that Kenobi on some level blames himself for the fate of his first apprentice, a lesson learnt in the hardest possible fashion...
A final duel offers the true master of the two a shot at redemption, after having taken it upon himself to right his wrongs and achieve oneness with the Force, the result being Obi-Wan's own death at the hands of his old apprentice. Anakin would later be restored to his old master's side following his act of self-sacrifice and the overthrow of the Empire - proving that at least some part of the man he had been under the mask was still there after finally having cast aside his initial aspirations towards the sort of power that eventually proved the Emperor's downfall.
Balance finally restored to the Force thanks to the neatly dovetailing, if at first seemingly massively different paths, of the man who had to learn how to be a father in spirit and the brother who should have been a son.
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