Obi-Wan Kenobi's whole existence in the Star Wars universe is tied up with the fate of Anakin
Skwalker — and their history is even longer and more complicated than you might think.
This is Obi-Wan's history with Darth Vader explained.
In The Phantom Menace, Obi-Wan tells his master, Qui-Gon Jinn, that he senses they've "picked up
another pathetic life form," referring to the young Anakin Skywalker. This line demonstrates
how, from the very beginning, Obi-Wan didn't think they needed extra baggage on their quest to
stop the Trade Federation's invasion of Naboo. In fact, Obi-Wan and Anakin never seem to gel in The
Phantom Menace. As Qui-Gon waits to hear if the Jedi Council will accept Anakin as an apprentice,
Obi-Wan even points out that his master's defiance is preventing his promotion to the Council itself.
Obi-Wan strictly adheres to the Jedi code and takes issue with Qui-Gon's constant rebellion
against it. However, when Qui-Gon is killed by Darth Maul, his dying request is that Obi-Wan
train the young Anakin. Obi-Wan himself briefly takes on Qui-Gon's rebellious spirit when he
tells Yoda he will train Anakin to fulfill this wish, regardless of whether the Council approves.
Obi-Wan's general fidelity to the Jedi Order and its
rules frequently contrasts with the older Anakin's perpetual rebellion against them.
However, the decision to go against the Council in the first place is handed down by Qui-Gon,
who planted a seed for the rift that would one day tear the galaxy apart.
From the start, Anakin Skywalker is depicted as a man of action, while Obi-Wan is a more careful and
analytical fighter. A perfect example of this takes place in Attack of the Clones, when Anakin
rushes in to fight Count Dooku, only to be knocked out by his enemy's Force lightning. Meanwhile,
Obi-Wan chooses to take a more defensive approach — and lasts longer in battle because of it.
While Anakin is seen as something of a prodigy, his reckless actions often
lead Obi-Wan to regard his apprentice with exasperation as well as admiration.
In the Clone Wars series, Obi-Wan frequently scolds Anakin for being too
fool-hardy while Anakin often calls out Obi-Wan for being too hesitant.
"We don't need a whole fleet, I can do this myself."
"Anakin, slow down and do what I tell you. It's more important to save lives than destroy ships."
Anakin leaps into battle without thinking about it and, thanks to his abilities,
always makes it out on the other side. On the other hand, Obi-Wan always tries to
evaluate every situation in order to come up with a proper plan. Of course, it's Anakin's
reckless need to take action that eventually leads him to the dark side. No doubt the older
Obi-Wan would have wished that he had taken this character flaw of Anakin's far more seriously.
A key facet of the Jedi code is that Force users should always avoid
personal attachments. Anakin shows us why this principle is so important because his
love of Padmé allows Palpatine to manipulate him into joining the Dark Side. However, Anakin's
attachment to his relationships isn't exclusive to Padmé. It also includes Obi-Wan himself.
"Obi-Wan is a great mentor, as wise as Master Yoda and as powerful as Master Windu."
Attack of the Clones demonstrates how deep their relationship goes when Anakin sees Obi-Wan come
under attack by droidekas. Anakin had earlier pointed out that Obi-Wan is the closest thing
he has to a father, and he clearly wants to save him from the droids — but he's torn
between that desire and his duty to protect Padmé. Thankfully, Padmé actually suggests
trying to save Obi-Wan themselves, giving Anakin the opportunity to set out to rescue his master.
Of course, it is this shared mission that cements Anakin and Padmé's love.
After their rescue mission fails and the two are sentenced to execution in a gladiatorial arena,
they share a kiss that later leads to marriage. Anakin's inability to deny his personal
relationships is a flaw in his Jedi mindset that recurs throughout the prequel era, eventually
leading to his fall from grace. His affection for Obi-Wan is a central issue in this dynamic,
making the history that Anakin, Padmé, and Obi-Wan share a very dangerous thing.
The Phantom Menace ends with Obi-Wan as a full Jedi Knight and Anakin as a Padawan. A decade
later, Attack of the Clones ends with Anakin's marriage and the beginning of the Clone Wars.
Following that, The Clone Wars covers the three-year gap between Attack of the Clones and
Revenge of the Sith. Given the amount of ground the series covers, it has to be inferred that,
when the First Battle of Geonosis takes place and the war begins, Anakin is
immediately promoted to Jedi Knight, as both he and Obi-Wan are generals in The Clone Wars.
From that time on, Obi-Wan and Anakin are seen as colleagues on more or less the same level,
and they are generally given the same level of responsibility in most situations.
It's worth remembering, however, that not only had Anakin just been promoted,
but he started his training considerably later in life than most Jedi. If Anakin had bristled at
Obi-Wan's instruction before, no doubt he really resents any perceived seniority by this point.
Obi-Wan, however, never seems to begrudge the fact that Anakin skips ahead to become his equal.
Anakin Skywalker was supposed to be Obi-Wan's student, and you would expect a master and
student relationship to continue in some shape or form even after their formal training ends.
That certainly seems to be the case with Yoda and his students,
as even Count Dooku views his old master with respect. Yet, perhaps because of Obi-Wan and
Anakin's closeness in age, their equal military ranks, and Anakin's exceptional
strength with the Force, they become more like brothers than a student and a teacher.
By the time Anakin is a full-fledged Jedi, he already seems to think of himself as superior
to his master. Obi-Wan is constantly advising prudence, while Anakin almost always thinks
immediate action is the key to victory. This difference leads to competition between the two
as they seek to prove that their approach is better. Anakin is especially eager to prove
that he's stronger than Obi-Wan, culminating in their duel on Mustafar, in which Obi-Wan
insists Anakin can't defeat him. The younger Jedi acts rashly and is left for dead as a result,
putting a final end to their long and fateful sibling rivalry.
Anakin tends to think that Obi-Wan is a model of self-control, to the point
where he mistakes Obi-Wan's adherence to the austere Jedi lifestyle for a lack of emotion or
passion. Yet we see in The Clone Wars that Obi-Wan understands Anakin's longings more
than Skywalker seemed to realize. He simply doesn't give in to them.
Take, for instance, Obi-Wan's history with Satine Kryze, the ruler of Mandalore. Their relationship
parallels the dynamic between Anakin and Padmé, as Satine is also a strong woman and political
leader. One Clone Wars story arc reveals that she and Obi-Wan once had a romantic connection,
though it's never clear if they acted on those feelings. However,
it's obvious Obi-Wan cares for her, and perhaps if he and Anakin had discussed
their forbidden romances it would have helped steer Anakin away from his eventual downfall.
Despite what Anakin might think, Obi-Wan also questions the Jedi Order from time to time.
This is first seen when he tells Yoda he will train Anakin no matter what the council
decides — but it is also made apparent with his reaction to the Jedi Order's vilification
of Ahsoka Tano for a crime he knows she did not commit. The real difference between these two
Jedi is how they handle their issues with the Jedi Order. For all his power, Anakin never learns to
control his emotions the way Obi-Wan does, despite Obi-Wan's pleas for his former Padawan to do so.
In Attack of the Clones, Anakin angrily complains to Padmé that Obi-Wan is jealous and holding him
back. Of course, this isn't the case at all. Obi-Wan only ever wants the best for Anakin,
believing that, despite the boy's exceptional skills with the Force, his Padawan needed to
mature emotionally in order to become a full Jedi Knight. Obviously, Obi-Wan was right.
Several times in The Clone Wars, Obi-Wan tells Anakin to play a situation carefully,
only to watch as Anakin rashly springs into action. Sometimes it works out, but other
times his brash choices lead to high casualties, or to Obi-Wan having to rescue the young Jedi.
What Anakin sees as Obi-Wan's jealousy is actually his master's desire to guide him to
reach his full potential. Eventually, when Obi-Wan confronts Darth Vader, the former apprentice
tells Obi-Wan not to lecture him, insisting that he sees through the lies of the Jedi.
By extension, he claims to see through the supposed lies that Obi-Wan had told him to keep
him from fulfilling his destiny. It's a tragic misinterpretation of their entire relationship.
In A New Hope, Obi-Wan says this of Anakin Skywalker:
"He was the best star-pilot in the galaxy and a cunning warrior."
More importantly, though, he adds:
"And he was a good friend…"
Anakin's inability to identify and control his emotions was a weakness that Palpatine
easily exploited. On the other hand, Obi-Wan may have felt a more profound love for Anakin
than his apprentice felt for him, simply remaining in control of those feelings.
Obi-Wan's heart breaks when he watches the security footage of Anakin killing younglings,
and on Mustafar, Obi-Wan laments that he has failed his young apprentice.
Obi-Wan retreated to the life of a hermit in order to hide from the Empire after the
destruction of the Jedi Order, but you can't help but wonder whether he also exiled himself
as punishment for preventing Anakin from falling to the dark side. When Obi-Wan appears in Rebels,
a deep sadness lingers over his bittersweet victory against his longtime rival, Maul.
In A New Hope, Darth Vader says that he feels Obi-Wan's presence on the Death Star, so there
can be doubt that Obi-Wan knew Vader was there as well. He chooses to go alone on his mission, in
part because the ever-contemplative Obi-Wan knows he will have to confront his former apprentice.
Looking at their final showdown from this point of view, it is a reasonable conclusion
that Obi-Wan believes his sacrifice to be penance for failing his old friend.
After Anakin becomes Darth Vader, Obi-Wan volunteers to watch over Luke on Tatooine.
He didn't have to do this, however. Obi-Wan could have left Luke to be
raised by the Lars family alone. Of course, he takes this mission
in part out of a desire to see a Jedi re-emerge and save the galaxy. However,
another part of him probably wants to protect the son of a friend he once cared very deeply for.
When Obi-Wan tells Luke about his father in A New Hope, he hides the true nature of his
relationship to Darth Vader, telling Luke that Vader betrayed and murdered Anakin Skywalker.
In Return of the Jedi, Obi-Wan famously claims that Anakin ceased to exist once he became Vader,
and that what he told Luke was true from a certain point of view.
It stands to reason that Obi-Wan would have held onto his feelings for his lost brother,
and that he probably saw it as his duty to watch over and protect his son.
It's a well-known fact that Obi-Wan won his victory over Anakin on Mustafar
because of his ability to claim the high ground. This slight difference in
elevation allows Obi-Wan to slice off Anakin's limbs after he attempts to go for the kill.
However, this line applies to more than just the physical difference between the two Jedi. Obi-Wan
has also gained the moral high ground here, and it's hard to argue otherwise — especially
considering that Anakin has just destroyed the Jedi Order he was sworn to protect,
slaughtered the younglings, and attacked his own wife.
Throughout the prequels and the series, Obi-Wan has a firmer grasp of morality
and duty than Anakin, who often acts for selfish reasons. And while more stories in the Star Wars
galaxy may find Obi-Wan struggling with the moral ambiguities of life outside the order,
he will no doubt always keep the high ground over his former apprentice.
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