Star Wars (Prequel Trilogy): Every Jedi's Greatest Failure
David Harth
Anakin Fighting Obi-Wan and Palpatine and Anakin
Anakin Fighting Obi-Wan and Palpatine and Anakin
The Star Wars Prequel Trilogy is one of the most controversial entries in the franchise. Lucasfilm has learned a lot of lessons from it but its story of the Jedi's manipulation by the Sith has gained a lot of fans in recent years. Those Jedi were led around by the nose by Palpatine as he played both sides to gain ultimate power. While there were some heroic acts during the Prequels, they all ultimately played into Palpatine's hands.
The Jedi's mistakes were the biggest, as they completely missed the power of the dark side growing under their nose. From the entire Order to the Council to individual Jedi, their mistakes doomed the Republic.

7 The Jedi Order Allowed Its Own weakening To Happen

The Jedi Order was one of the most powerful groups in the entire Republic, beholden to the Senate and the Supreme Chancellor, the guardians of justice in the galaxy. However, that was the problem with the Jedi and it's where their biggest mistakes stemmed from. The Jedi Order, instead of being a dynamic, changing body, took on the attributes of the Republic it protected, becoming bureaucratic and obsessed with the Rule of Law.
This led to its downfall as surely as anything else and it's one of the advantages the Sith had over them; the Sith were dynamic and forced to adapt to situations because of their numbers, whereas the Jedi were secure in their power and thought themselves unassailable. They didn't realize their codes and rules made them brittle and easy to break.

6 The Jedi Council Trusted In Their Power To Weather Any Storm

Jedi Council during Attack of the Clones
Jedi Council during Attack of the Clones
The weakening of the Order started at the top and the Jedi Council moved the Order into the direction that would spell doom for it. The Council was composed of some of the most powerful Jedi in the galaxy, beings who were secure in their powers and their ability to listen to the will of the Force. However, like the rest of the Order, they became like the Senate, a bloated body full of powerful functionaries.
That power would fail when Palpatine started to turn up the heat on the Order. The Council was so secure in their power that even when the dark side clouded their ability to see the future, they didn't despair. They thought they were untouchable. A supposition that would prove false when Palpatine's plans went into full swing.

5 Ahsoka Tano Allowed Her Disillusionment With The Jedi & The War To Drive Her From The Order

Ahsoka Tano in Star Wars: The Clone Wars
Ahsoka Tano in Star Wars: The Clone Wars
Ahsoka proved her worth during the Clone Wars, but war is hard on adults and she was just a teenager. The straw that broke the camel's back was the bombing of the Jedi Temple and the revelation that her friend Barriss Offee was behind it. The war had broken the young Padawan and that had a profound effect on Ahsoka. She quit the Order in disgust over it and the Order's response to Offee's crimes.
While she would come back to help out at the end of the war, if she had stayed with the Order, with Anakin, there's a good chance she could have taken him off of his dark path. Ahsoka couldn't handle the stresses of war and the way it affected people. That failure to cope caused great suffering.

4 Mace Windu's Failure To Kill Palpatine Doomed The Republic

Mace Windu in Star Wars: Revenge of the Sith
Mace Windu in Star Wars: Revenge of the Sith
Mace Windu could have ended the whole thing before it even happened if he had been better. He and a group of Council masters went to arrest Supreme Chancellor Palpatine and the battle cost all but Mace their lives. The Jedi and the Sith battled it out, with Windu able to keep up with the Sith Lord. It's hard to know if Palpatine could sense Anakin coming and stalled but the fact of the matter is Windu should have killed Palpatine when he had the chance.
He had the Sith Lord down, dead to rights, and hesitated, trying to get Anakin to agree with him. If Windu just would have killed Palpatine immediately instead of talking to Anakin, things would have gone way better.

3 Yoda's Failure To See Through Palpatine's Lies Doomed Everyone

Yoda holds his green lightsaber
Yoda holds his green lightsaber
Yoda was one of the Order's most venerable Masters, but that doesn't mean he was the best Jedi. Yoda was just as responsible for what happened to the Jedi Order as anyone, so sure was he in its power and the righteousness of its cause. He let all of his experiences, all of his mighty powers, all of the greatness of the Jedi Order blind him to the threat growing right there in front of him.
Palpatine's lies and cunning were powerful but Yoda had almost a millennium of experience and was one of the most powerful Jedi Masters ever. The fact that he never put two and two together, even as Palpatine became more openly antagonistic and dictatorial, even as the Force was more and more clouded, was a death knell for the Jedi. Yoda never saw through the lies being told right to his face and that doomed the Republic.

2 Obi-Wan's Failure To Kill Anakin Doomed Millions At The Hands Of Darth Vader

Obi-Wan Kenobi and Anakin Skywalker's relationship was one of the most unique in the Jedi Order. They were brothers as much as they were partners and they worked together flawlessly. Many foes lost to the pair and the two of them were an unstoppable team. However, Obi-Wan missed a lot of what was going on under the surface with Anakin, things that would see Anakin fall to the dark side.
Obi-Wan was a great brother to Anakin but not a great Master. Eventually, the two of them would come to blows, a battle that Obi-Wan won, literally disarming (and dislegging) his former student. However, instead of ending the life of his fallen student, he let him live. While it wouldn't have ended the Empire to kill Anakin, it would have saved countless lives in the long term and hurt Palpatine's control over the galaxy in the short term.

1 Anakin's Failure To Realize What Palpatine Was Doing Doomed Everyone

Lots of people failed Anakin—including the Jedi Council—but his own failure with Palpatine doomed everyone. Anakin felt like he was greater than he was given credit for and Palpatine was there to pad his ego. Anakin's life as a slave and the loss of his mother messed him up immensely and his search for someone, anyone, to love him led him to believe everything Palpatine told him.
Anakin's inability to see through Palpatine and what he was doing led to him trying to save the Sith Lord from Mace Windu, which led directly to him becoming Darth Vader. His desire to save his wife was greater than his common sense and he made the mistake of thinking he could trust the galaxy's greatest manipulator, a move that lead to untold suffering.