5. A friend betrayed by the Jedi
The Clone Wars did much to explore the ways in which Anakin became disillusioned with the Jedi, and episodes 7-20 of season 5 was the perfect example. After a mysterious Jedi temple explosion, believed to have been committed by a Jedi, Anakin and Ahsoka investigate. The investigation leads to a series of events that make Ahsoka look like the Jedi responsible for the bombing. Ahsoka is arrested, tried, found guilty, and expelled from the Jedi Order, but Anakin doesn’t believe she’s guilty.
While Ahsoka is on the run from the Jedi and the Republic, Anakin launches his own investigation to find the person responsible for the bombing and framing of Ahsoka. He’s the only one who believes in Ahsoka’s innocence, and he’s not willing to let her fate be decided by a Jedi order that won’t listen to reason. His investigation leads him to discover that Ahsoka’s friend and fellow Padawan Barriss Offee bombed the temple, believing the Jedi have lost their way and were never meant to become military officers, and framed Ahsoka for the crime.
Even though Ahsoka is cleared of all charges, she feels betrayed that the Jedi council didn’t believe her, and she decides to leave the Jedi order. Anakin is heartbroken to lose Ahsoka, and the events likely had a lasting impact on his opinion of the Jedi from that moment until his own betrayal of them.