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Ever since Anakin was brought in the Order, the Jedi have been skeptical and even fearful of him due to his struggles with emotions that they felt were synonymous with the Dark Side. Fear, hate, and anger. However, in Revenge of the Sith, the Jedi chose Anakin to spy on the Chancellor, despite their distrust of him.

OBI-WAN: "Anakin did not take to his new assignment with much enthusiasm."

MACE: "It's very dangerous putting them together. I don't think the boy can handle it. I don't trust him."

If they doubt Anakin's ability to perform his task that much, why not just send Obi-Wan with him to keep an eye on Anakin, and to have an extra set of eyes on investigating Chancellor Palpatine?

  • Palpating would have become suspicious seeing Obi Wan there constantly, as would Anakin. Not to mention it would have caused the already growing tension between Anakin, Obi Wan, and the Council to boil over into something worse. – MissouriSpartan Dec 29 '19 at 20:45
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    His new assignment is to spy on Palpatine for the Jedi Council. If Obi-Wan (a member of the Jedi council) was there in the room with Anakin and Palpatine, it wouldn't be much of a spy mission – Valorum Dec 29 '19 at 21:24
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    Also, Anakin already had easy access to chancellor, so he was the obvious candidate for the job. – Rebel-Scum Dec 29 '19 at 21:27
  • Considering everything Anakin was trusted with during Star Wars: The Clone Wars, Mace's quote here is even more difficult to believe. Anakin was constantly trusted with the a large amount of Republic assets like ships and troops, and even the lives of other Jedi (including his own padawan). Anakin's droid even saved Anakin's and Mace's life once. So I find it hard to reconcile "Here, take your Jedi padawan and this capital ship with a squadron of fighters and ground troops and attack this target" with "I don't trust you, but go spy on the Chancellor anyway". – Ellesedil Dec 30 '19 at 18:09
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    @Ellesedil -- It could be that Master Windu did not trust Anakin, but perhaps the others did. Clearly Obi Wan thought he was the chosen one, and right up to the end refused to entertain the idea that Anakin was a rotten apple. Clouded the dark side is. Difficult to see are the shadows moving within the shadows. – elemtilas Dec 30 '19 at 19:30
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It was not a matter of choice in the first place. Anakin was actually seen as a spy of opportunity; since Palpatine, for his own reasons, had started spending increasingly time with him, showed that he trusted him, and had just appointed him as his own personal representative on the Jedi Council - something that had never happened until then, since the Council elected their own members:

Palpatine: Anakin, I'm appointing you to be my personal representative on the Jedi Council.

Anakin: Me? A Master? I'm overwhelmed, sir

The Council accepted Anakin's appointment, but without extending to him the title of Master, something that Anakin, in turn, finds insulting, and helps to his gradual alienation from the Council and the Jedi Order.

So, since the Council had already a Jedi close to Palpatine, they decided to try to use it for their own benefit to the extent possible, by asking him to inform them on the Chancellor's dealings. Interestingly enough, they do not ask him in a formal session, but through Kenobi, in what would seem to be a private and informal conversation, had Kenobi not made clear that this was a Council request:

Obi-Wan: The only reason the Council has approved your appointment is because the Chancellor trusts you

Anakin: And?

Obi-Wan: Anakin, I'm on your side. I didn't want to put you in this situation.

Anakin: What situation?

Obi-Wan: The Council wants you to report on all the Chancellor's dealings. They want to know what he's up to.

Anakin: They want me to spy on the Chancellor? But that's treason.

Obi-Wan: We are at war, Anakin.

Anakin: Why didn't the Council give me this assignment when we were in session?

Obi-Wan: This assignment is not to be on record.

[...]

Anakin: You're asking me to do something against the Jedi code, against the Republic, against a mentor and a friend - that's what is out of place here. Why are you asking this of me?

Obi-Wan: The Council is asking you.

(To be honest, we never see the Council discuss this, and there is at least a hint that this may be a request not of the Council but of some inner circle - Mace, Obi-Wan, and Yoda.)

So, given this situation, there was never any option of Kenobi or anyone else actually stepping in and assisting or supervising Anakin in any way; it was a matter of Anakin being their only option for the task, no matter if some could not actually trust him for this. There was never any choice "we need to put someone close to the Chancellor - who would be appropriate?"; the initiative had always been with Palpatine here, starting with Anakin's peculiar and unprecedented appointment. And judging from the rest of the story, he played his cards too well.

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  • For the record, Anakin isn't insulted by the refusal of the rank of Master, he's gutted because he was hoping to access the Jedi's secret Master-only archives which potentially had the solution to Padmé's force-vision-observed death. – Valorum Dec 31 '19 at 0:24
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    @Valorum that's maybe an interesting opinion. For the actual record, he uses the word "insulting" himself talking to Obi-Wan, just before the dialogue between themselves I have quoted - I wouldn't have used the term myself here if this was not clearly the case. – desertnaut Dec 31 '19 at 0:33
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    @Valorum plus, at the time Palpatine had not yet told Anakin about Darh Plagueis the Wise, who could supposedly create life and keep his loved ones from dying. – desertnaut Dec 31 '19 at 1:21
  • I can't help but also see some face-saving/retribution by the council in this appointment. Palpatine forced something unheard of - so they try something equally unheard. At least they were able to proof themselves and Anakin they were able to do it. – bdecaf Dec 31 '19 at 10:32

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