Hands down, I would choose Ahsoka Tano to challenge Darth Vader.
It has been many years since I have seen The Clone Wars and freshened up on all the lore so forgive my lack of Star Wars knowledge!
Ahsoka Tano is one of only a handful of people that could have knocked Anakin back to his senses that the dark side is not the way to go. Being a gray jedi herself, she did not have the holier than thou mentality of the jedi counsel as she was fully aware of the persuasion of the darkness. Instead of burying those feelings and struggles, she embraced them and strengthened herself to effectively combat the darkness within her.
Also having been a padawan to Anakin, she would already be all too familiar with his own struggles, thus coming off as more understanding and loving than the judgmental Jedi counsel. Asoka believed in redemption and showed tremendous amounts of grace and forgiveness, which is ultimately what Darth Vader needed.
I think it would have been extremely interesting if Darth Vader had his whole redemption arc with Ahsoka instead of waiting all that time for Luke to grow up and begin entangling himself with Palpatine as well. It makes you wonder how different the Empire would have been.
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