Star Wars was envisioned by creator George Lucas as a story about the rise and fall of Darth Vader. The Prequel Trilogy focused on the relationship between Anakin Skywalker and Obi-Wan Kenobi, chronicling the young Jedi's fall to the dark side using expert world-building, something Lucasfilm has seemingly forgotten how to do since Lucas left. The movies went into their relationship, one that was expanded upon by The Clone Wars cartoon, and showed the highs and lows of their partnership.
While the two men became like brothers, Obi-Wan might not have been the best choice as Anakin's master as he made a lot of mistakes during his training, ones that inadvertently led to the rise of Darth Vader.
10 He Shouldn't Have Let The Council Give Anakin A Padawan
Everybody loves Ahsoka Tano, but it just feels like a very weird thing for the Jedi Council to assign her to Anakin as a Padawan to teach him responsibility. Obi-Wan definitely should have stepped in at this point because while Anakin had a lot of strengths as a Jedi, he certainly wasn't ready for a Padawan.
The Council was often pretty monolithic but as Anakin's master, Obi-Wan knew him better than anyone else and his opinion on his student would have been honored. He should have said something because foisting that kind of responsibility on Anakin while at war couldn't have helped the young Jedi's mental state.
9 He Should Have Kept A Tighter Watch On The Relationship Between Anakin & Palpatine
Palpatine took a keen interest in Anakin from the start and it's honestly a little weird that no one questioned it. How many times in the history of the Republic had its Supreme Chancellor decided to spend so much time with a junior member of the Jedi Order? The fact that no one questioned it is strange, to say the least, and Obi-Wan should have definitely done so.
Anakin's power level was great but when it comes right down to it, he wasn't among the most respected Jedi of the Order and Obi-Wan should have questioned why the Chancellor was so interested in him.
8 He Should Have Helped Anakin Become More Patient
One of Anakin's biggest flaws as a Jedi was his lack of patience. Part of it definitely has to do with the fact that he knew his own potential and felt that he wasn't reaching it yet but another factor was his age —he had started training so much later than others and while he still came along quickly, he felt like he should be farther along, especially compared to some of his peers.
Anakin's impatience would lead to some pretty bad places for everyone and if Obi-Wan had worked harder with him on it, there's a chance things would have been very different for everyone.
7 He Should Have Curbed Anakin's Recklessness More
Anakin was quite reckless and while Obi-Wan often chided him for it, he also sort of encouraged it. A big part of The Clone Wars was Obi-Wan trying to do things in a well-thought-out manner and Anakin rushing in, with the two meeting in the middle and combining their approaches. While this was successful, it set a bad example for Anakin.
If Obi-Wan would have worked harder to curb Anakin's reckless behaviors, things would have turned very different. Unpredictability is good but Anakin's tendency to rush into things and let them sort themselves out was a detriment to everyone.
6 He Should Have Pushed Harder For The Council To Make Anakin A Master
Everyone remembers the scene where the Council admits Anakin to the body and he throws a bit of a fit because he isn't made a Jedi Master. It was one of many bricks that Palpatine used to widen the wall between the Jedi and Anakin, and if Obi-Wan had pushed the Council harder to make Anakin a master a lot of problems could have been solved.
Obi-Wan had fought side by side with Anakin for years at this point. He knew just how good Anakin was and, most importantly, the kind of person he was. He would have known how much the title meant to Anakin and pushing the Council to give it to him would have been a great use of Obi-Wan's time and influence.
5 He Should Have Set A Better Example
Obi-Wan Kenobi has a lot of fans, but looking at his actions and attitudes throughout the Saga, one can see that he wasn't exactly the best Jedi around. Obi-Wan wasn't exactly a paragon of Jedi virtues and Anakin picked up a lot of his bad habits over the years. This compounded the problems Anakin already had.
Being responsible for training a Padawan, especially one like Anakin, is hard work and demands a virtuousness that Obi-Wan often couldn't even fake. Anakin learned how to do things the Obi-Wan way and that way wasn't exactly the best way to do things.
4 He Shouldn't Have Patronized Anakin So Much
Obi-Wan had a certain way about him. He was a rather sarcastic person and enjoyed quipping and poking fun at others. He was a lot of fun to be around but he could also be pretty patronizing and he had a tendency to patronize Anakin more than was necessary. Anakin was a rather volatile young man and he didn't see the humor in being treated that way.
While there was no doubt that Obi-Wan and Anakin loved each other, the way Obi-Wan treated Anakin wasn't always the best for their relationship. The constant needling didn't do anything positive for Anakin and he definitely could have done without it.
3 He Should Have Helped Anakin More With His Problems
Obi-Wan was one of the better Jedi to have at one's side in a fight but there were a lot of places he was deficient. Anakin was a person with a lot of problems that he needed help with and Obi-Wan wasn't the best person to help him with those sorts of things. Part of it is the fact that Obi-Wan was raised in the Jedi Order —he wasn't very good at dealing with feelings.
Anakin was taken from his mother at a formative age, thrust into a monastic order, then lost his mother, committed a terrible atrocity, and was embroiled in a galactic war. He never got time to deal with issues and Obi-Wan could have been more helpful with all of that.
2 He Should Have Noticed The Relationship Between Anakin & Padmé
In general, the fact that no one knew about the relationship between Anakin and Padmé is pretty unbelievable but for Obi-Wan not to notice is especially bad. It really shows how little attention he paid to Anakin in general.
The obliviousness that it takes not to notice it is astounding. Obi-Wan had experience with Satine Kryze that would have given him insight into how Anakin felt for Padmé and while it's doubtful Obi-Wan would have made his friend give up his relationship, he could have helped his young apprentice with it more, perhaps even teaching him how to deal with the whole thing in a more mature manner.
1 He Shouldn't Have Grown So Close To Him
The Master-Padawan relationship was different for every pair and Obi-Wan and Anakin's was quite unique. The two Jedi were extremely close, like family, and that led to some good and bad things. Anakin already had a problem with attachment and there's a good chance that if Obi-Wan had kept himself more distant from Anakin, Anakin would have respected him and listened to him more.
Both men were reaching out for some kind of belonging and found it in each other but their close relationship wasn't good for either of them. They had a familiarity that allowed them to work well together as partners but as teacher and student, they were just too close.