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In Episode III Revenge of the Sith, Obi-Wan Kenobi says the following:

Obi-Wan Kenobi: Chancellor.
Anakin Skywalker: Are you all right?
Palpatine: [looking behind them] Count Dooku.
Obi-Wan: This time, we'll do it together.
Anakin: I was about to say that.
Palpatine: Get help. You're no match for him, he's a Sith Lord.
Obi-Wan: [turns and smiles] Chancellor Palpatine, Sith Lords are our speciality.
Count Dooku: Your swords, please. We don't want to make a mess of things in front of the Chancellor.
Obi-Wan: You won't get away this time, Dooku.
Dooku: I've been looking forward to this.
Anakin: My powers have doubled since the last time we met, Count.
Dooku: Good. Twice the pride, double the fall.

At that point, Obi-Wan was looking very confident that he can easily deal with Dooku. Or is he simply arrogant because he defeated Darth Maul ?

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    It's, unfortunately, just another Episode III Obi-Wan bad one-liner. – Bob Feb 14 '17 at 11:10
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    "My powers have doubled since the last time we met" Is it really that easy to measure Jedi skills and Force abilities? It seems so silly to say that. – Oubliette Feb 14 '17 at 11:18
  • If he's arrogant because of defeating Darth Maul, then it is well earned arrogance. No other Jedi defeated a Sith Lord in a long time, and Obi-Wan was just a padawan when he did. – RichS Feb 14 '17 at 14:53
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    @Withywindle Saying his powers have doubled since the last time is as silly as measuring Force abilities by counting tiny unicellular creatures. ... oh wait ... nevermind. – RichS Feb 14 '17 at 14:54
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    @RichS So did his "midichlorians" double? Also, "midichlorians" should have been named differently, it sounds so scientific and stale. I cant help but think of MIDI and Chlorine whenever I hear it, which is unfortunate. – Oubliette Feb 14 '17 at 14:58
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It's part arrogance, part experience.

(The following is Disney Canon)

Both Obi-Wan and Anakin have grown between the end of Episode II, where they got beat pretty badly by Dooku, and Episode III, where Obi-Wan still gets beat pretty badly, but fortunately Anakin is way stronger.

During the Clone Wars, the two of them battled against both Count Dooku and Darth Maul on many occasions. On each of these occasions, while neither side was able to ultimately kill the other, Obi-Wan and Anakin were definitely on the winning side.

With the clone wars reaching their end in Episode III, it's no surprise that Obi-Wan was feeling confident. His enemies were on the ropes and the republic were mopping up what was left of them. So when Dooku walks in, Obi-Wan doesn't see him as a powerful Sith Lord to be wary of, but rather somebody who hasn't been able to kill him, even with help from Darth Maul, over the years. There's also the fact that Super-Anakin is with him on this occasion as well, so where before Obi-Wan might still emerge victorious in a 1v2 against Sith Lords, he's now in a 2v1 against just Dooku. The odds are certainly in Kenobi's favour, or so he believes.

Basically, his reaction amounts to "Oh, for the love of.... Dooku again? Be right back, Chancellor, we'll just deal with this, then untie you, won't take a sec, kicked him and his buddies to the curb hundreds of times, don't you worry."

Of course, this arrogance is probably what led to him getting smacked across a room and knocked unconscious.

TL;DR - He's fought and won against Dooku multiple times during the Clone Wars. To Kenobi, Dooku is more of a thorn in his side than a worthy adversary at this point.

BONUS OUT-OF-UNIVERSE ANSWER: It's yet another Ewan McGregor ad-lib.

  • One should note that Obi-Wan does not get beat badly by the virtue of Dooku alone. Palpatine uses the force to make Obi-Wan unable to defend himself, since he wants Anakin to beat Dooku. Obi-Wan cannot block this since he does not suspect it at all. – MooS Feb 14 '17 at 16:28
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    @Moos where did you get that info that palpatine itnerfered in the fight? – Thomas Feb 17 '17 at 7:16
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    @MooS - There's nothing in the script to indicate that Palpatine interfered in the fight. – Valorum Feb 17 '17 at 9:14
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    I mean, if you watch the movie scene, you can pretty clearly see that Dooku is able to use the force on Obi-Wan twice, the first time pushing him back and the second time lifting him and hurling him across the room. You could just as easily say that Dooku simply got the better of him. Besides, if your source is Legends canon and not Disney, it sadly doesn't have any bearing on my answer. – DisturbedNeo Feb 17 '17 at 9:52
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    Well, maybe he's just rooting for Anakin by bobbing his head, and not using the force at all. You can't say for sure, not without solid evidence. And all I was saying is that if you can provide solid evidence, it has to be considered Disney Canon for me to update my answer. If you can show me some novel saying Palpatine helped Dooku, then fine, but if that novel is considered Legends canon for whatever reason, then it makes no difference, because my answer is specifically Disney canon. – DisturbedNeo Feb 17 '17 at 13:51
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There were two of them, and only one of him. Earlier, Anakin tried to go it alone against Dooku, and was taken out. Obi-Wan then also failed against Dooku. Then, Anakin tried again alone, and failed.

They'd also both become more skilled since fighting him, whereas Dooku had likely already reached the peak of his skills. Keep in mind that Anakin especially was fairly inexperienced when they first encountered Dooku. Also, being the leader of the droid army probably didn't leave much time for practicing lightsaber skills.

Recall, also, that Obi-Wan was of roughly equal power with Anakin, because he fought him to a standstill later on (until Anakin was stupid enough to attack higher ground). Either of them alone at that point could have taken out Dooku. My impression was that Sidious interfered to remove Obi-Wan from the fight, so that he could convince Anakin to kill Dooku.

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