Anakin Skywalker is probably one of the most complicated and well fleshed out characters in Star Wars. The character has appeared in more Star Wars media than any other, with his struggles against the dark side being a huge part of the Saga. Anakin's time as a Jedi wasn't easy, and while he was one of the Republic's greatest heroes, he was also a mess on the inside.
Anakin did make many friends during his time as a Jedi, many of whom tried to help him stay on the straight and narrow. They'd all ultimately fail as Palpatine would convince Anakin that the Sith way could help him more than the Jedi ever could.
10 Mace Windu Was Too Late In Trying To Kill Palpatine
Mace Windu was probably the master who was most leery about Anakin's place among the Jedi. However, that's just kind of Jedi Windu was--a serious person whose entire life was making sure the Order was safe. While he didn't always appreciate Anakin's attitude and hot-headedness, he did realize just how important Anakin was to the Jedi war effort and tried his best to help him at times.
The irony is as much as they clashed, and Windu would have been a good master for Anakin, as both Jedi were of the more martial variety. Windu's biggest failure with Anakin, though, had nothing to do with their personal relationship--if Windu had succeeded in killing Palpatine before Anakin got to the Chancellor's office, none of the calamities of the end of the Clone Wars would have ever happened. However, Windu's skill failed there and the rest is history.
9 Jar Jar Binks Was Too Easily Manipulated
Jar Jar Binks has gone through a weird time in his existence. He went from one of the most derided parts of the Prequel Trilogy to a much more well-liked character, with the Darth Jar Jar fan theory among the most popular Star Wars fan theories ever. Jar Jar and Anakin were friends, and while the Gungan caused a lot of trouble, it wasn't his clumsiness that made him fail Anakin.
Instead, it was how easily manipulated he was. Jar Jar introduced the Emergency Powers Act to the Senate, giving Palpatine the tools he would need to become Emperor later and playing right into the Sith Lord's hands. If Jar Jar had never fallen for Palpatine and Mas Ameeda's tricks, much suffering would have been averted and Anakin's fate would have been different.
8 Watto Treated Anakin Well But Kept Him As A Slave
Calling Watto Anakin's friend may seem like a stretch since he owned the boy, but he actually treated Anakin very well, at least for a slave. Anakin and Shmi had a nice place to live, were well-fed and taken care of, and Watto made sure the boy not only had toys but machines to tinker with. He tried to give Anakin a good life despite the circumstances of their relationship.
However, just the fact that Anakin grew up as a slave was enough to set him down the path he found himself on. It was within Watto's power to free Anakin and his mother at any time and he didn't, which only added to Anakin's mental issues. In fact, he could have released Shmi to Qui-Gonn as well, which would have made a huge difference in Anakin's life but he didn't.
7 Plo Koon Couldn't Get Through To Anakin With His Teaching On Patience
Anakin and Plo Koon worked together to take down the Separatist Dreadnought the Malevolence and had a good working relationship. While Koon was the senior Jedi Master, his task force had been destroyed by the massive ship, and he allowed Anakin to take the lead. However, he tried to temper Anakin's impetuousness, working to teach the young Jedi patience and tactics.
However, his teaching would prove to fall on deaf ears. Anakin would never stop being a hothead, and this tendency of his would be one of the things that put him on the path to dark side. If Koon had been able to get through to Anakin, perhaps the young Jedi's life would have been different.
6 Captain Rex Couldn't Help Anakin Work Through His Issues
Captain Rex was Anakin's second in command in the 501st and one of the most formidable clones in the Grand Army of the Republic. The two were more than a general and his second, though, becoming great friends and developing a great working relationship.
However, no matter how many times they triumphed or how great their friendship was, Rex could never help Anakin deal with his issues. Their victories and friendship never showed Anakin that there was more to life than loss and despair, an attitude that dogged Anakin throughout his life and led him to some dark places.
5 Yoda Didn't Treat Anakin As A Special Case
Yoda was the leader of the Jedi Council, making him the most important General in the entire Grand Army of the Republic. His failure with Anakin was really quite simple when it came down to it--he was treating him like he would treat any other Jedi. While Yoda understood that Anakin was a special case, he did what he always did and was met with failure.
In fact, Yoda's failure with Anakin is a microcosm of his failure with the Republic in general--he kept trying to do things the way he always he did, trusting his years of experience to get him through a situation that was unprecedented in his life. Yoda's failure would show that he wasn't as great of a Jedi as everyone thought and spell doom for the Jedi Order.
4 Ahsoka Tano Couldn't Get Anakin To Open Up
Ahsoka Tano was Anakin's apprentice, given to him by the Jedi Council in an effort to get him to mature. The two would become great friends over the course of the Clone Wars, forming a bond that made both of their lives better during one of the most trying times in the galaxy's history. However, that friendship wasn't enough to save Anakin.
His stewardship of Ahsoka never taught Anakin what the Jedi Council thought it would. While Ahsoka frequently tried to be there for her master, she was unable to get him to open up to her and share his problems. If she could have gotten him to open to her, much sorrow may have been averted.
3 Padme Amidala Didn't Tell Anyone About Anakin Killing An Entire Village Of Tusken Raiders
Padme's failure with Anakin was allowing their relationship to progress at all. Their relationship was full of red flags pretty much from the start, led to some of Anakin's most terrible acts, and would end with Padme's death. Padme's biggest failure, though, was not telling anyone about Anakin killing an entire village of Tusken Raiders.
This act of revenge showed exactly what Anakin was capable of, and there's a chance that if Padme had told someone about it, like Obi-Wan, they could have helped Anakin work through his anger and sorrow in a healthier way, perhaps preventing the tragedies of his future.
2 Qui-Gon Jinn Died Too Soon
Qui-Gon Jinn freed Anakin from a life of bondage, giving him a chance at a better life, but his failure to stay alive would doom Anakin. Qui-Gon's belief in the prophecy of the Chosen One made him the perfect person to train Anakin, and Qui-Gon's patience and wisdom would have made a huge difference in Anakin's life. Qui-Gon's death pretty much doomed Anakin to his fate.
If Qui-Gon would have waited for Obi-Wan to get to him instead of going and facing Maul himself in the power core, he would have survived to train Anakin, and things would have been much better for the young man. However, Qui-Gon's failure to survive was one of the main contributing factors to Anakin's terrible fate.
1 Obi-Wan Kenobi Knew He Had Failed Anakin
Obi-Wan Kenobi and Anakin Skywalker's relationship ended in a terribly sad fashion made all the worse by the fact that Obi-Wan knew he had failed Anakin, and not just in way one way. During their final battle, Obi-Wan realized just how much he had failed the young Jedi that he considered a brother, and it broke his heart.
Obi-Wan did his best with Anakin, but he wasn't as a great Jedi as he thought he was. This failure would cause untold suffering throughout the galaxy and set the two men on a collision course that would end in the corridors of the Death Star.
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