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I know that there is a sort of similar question about how Princess Leia knew about Obi-Wan here, but I'm curious as to why and how Princess Leia thought an aging Obi-Wan Kenobi would be of any help to the Rebellion worth risking herself and her crew in addition to the stolen Death Star plans (which apparently the Rebellion only had stored on R2-D2 physically, and no other copies)?

See here for the scene in question.

Things to consider:

  1. Obi-Wan as a resource to the Rebellion didn't even have his own ship or own resources to contribute (not even enough to pay for passage for a smuggler to transport him).
  2. Obi-Wan as a fighter did not do any extensive amount of fighting in A New Hope (he cut off a guy's arm in a bar, and sacrificed himself vs Darth Vader, that's it)
  3. Obi-Wan as a Jedi didn't have an apprentice yet, and was probably not going to have a shot at taking on Darth Vader or the Emperor.
  4. Princess Leia risked near everything just to visit in person the place where she thought Obi-Wan still lived (he could have been dead for years assuming that she said "years ago" in her message to Obi-Wan regarding how she knew of him). She risked herself, her ship, her crew, her cause (if she had been tortured into giving up the Rebellion) and the stolen plans themselves (next time stormtroopers, shoot down the empty escape pod, if for no other reason than to improve your atrocious aim and shooting during the original trilogy), just to see if Obi-Wan might be interested if still alive to maybe (somehow) help the Rebellion.

Possible answers I've considered (I'm curious for more though):

  1. Obi-Wan might have some sort of wisdom or knowledge about attacking the Death Star and he may have been able to analyze the stolen Death Star plans for weaknesses (but the Rebels did a good job of this anyway).
  2. Obi-Wan would have been exceptional at espionage and infiltration (took out the tractor beam on the Death Star, successfully avoided almost every stormtrooper he encountered, and Jedi mind tricked the ones he couldn't avoid -- think "these aren't the droids you're looking for"), although Obi-Wan's stealth would not have been needed inside the Death Star had Leia not gotten herself captured and in need of a rescue from the Death Star in the first place, which happened as a result of trying to visit Obi-Wan.
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At the time Leia recorded the message, and as far as she was concerned, Obi-Wan would have genuinely been her only hope.

As she says in the message:

I regret that I am unable to present my father's request to you in person, but my ship has fallen under attack and I'm afraid my mission to bring you to Alderaan has failed.

So therefore the "only hope" is evidently only relevant following the events at the start of the movie, i.e. the attack by the Star Destroyer on the Tantive IV and Leia's capture.

To summarize, and with specific reference to points in your question:

  • Leia's original mission was to bring Kenobi to Alderaan to assist in the Rebellion (the nature of this proposed assistance is left uncertain).
  • At this stage Kenobi is not yet her only hope; however her ship is attacked.
  • She records the message after the attack but before her capture.
  • And so her plans need to change and now Kenobi becomes her only hope.

Edit to Clarify

We are of course not talking about rescuing Leia here; what we are talking about is Obi-Wan being her only hope of getting the Death Star plans to the Rebellion following her capture. As her recorded message says:

I have placed information vital to the survival of the Rebellion into the memory systems of this R2 unit. My father will know how to retrieve it. You must see this droid safely delivered to him on Alderaan. This is our most desperate hour. Help me, Obi-Wan Kenobi, you're my only hope.

It should be clear from all of the above that Leia's original motive in visiting Tatooine was to bring Obi-Wan to Alderaan to assist the Rebellion, but after she was captured her motive changed to having Obi-Wan bring R2 to Alderaan with the Death Star plans. This is then precisely what Obi-Wan proceeds to do:

You must learn the ways of the Force if you're to come with me to Alderaan.

Han Solo. I'm captain of the Millennium Falcon. Chewie here tells me you're looking for passage to the Alderaan system.

Looks like we're coming up on Alderaan.

And just to be even more clear: rescuing the princess was never intended - it only became an objective after the Falcon was captured by the Death Star and they discovered that she was being held on it.

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    In the radio play, it's made more apparent that the intention was to visit him, then they were attacked, not the other way around.
    – Valorum
    Feb 1, 2015 at 0:32
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    @Richard - I think that comes across well enough in the movie too. It seems clear that they were on the way to visit him, they were attacked, and after the attack was when Leia recorded the message (hence "my ship has fallen under attack" in the message). So he wasn't her only hope until she recorded the message, which was after the attack.
    – user8719
    Feb 1, 2015 at 0:41
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    @Richard I'm genuinely confused as to whether you mean the Rebellion or the Empire, so I thought I'd point out that you typed "Republic." They're not really a friend to either one; seems like they mostly either do farming or criminal activity.
    – jpmc26
    Feb 1, 2015 at 7:53
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    @jpmc26 - Don't forget that for the majority of people, the Empire is simply a continuation of the existing Old Republic. There's minimal indication they would provide succour to Leia.
    – Valorum
    Feb 1, 2015 at 9:36
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    @MatthewRead - What you've missed is that it's not about rescuing her. "I have placed information vital to the survival of the Rebellion into the memory systems of this R2 unit. My father will know how to retrieve it. You must see this droid safely delivered to him on Alderaan. This is our most desperate hour. Help me, Obi-Wan Kenobi, you're my only hope." - Obi-Wan was her only hope for getting the Death Star plans to the Rebellion.
    – user8719
    Feb 2, 2015 at 7:40
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Based on the end of Revenge of the Sith, Leia's adoptive father, Bail Organa was the only person other than Yoda and Obi-Wan who was aware of Luke and Leia's true parentage, and hence was privy to Obi-Wan and Yoda's master plan.

Consider the same line that Darth Satan quoted:

I regret that I am unable to present my father's request to you in person, but my ship has fallen under attack and I'm afraid my mission to bring you to Alderaan has failed.

Leia's mission was not to retrieve Obi-Wan specifically. I don't know of a specific reference, but given the timing and the ages of the Skywalker children, her father probably sent her there to get Obi-Wan with the specific intent of retrieving Luke as it was time to for him to fulfill his destiny.

However, in order to preserve the secret, Leia was not likely told the whole truth (in the same manner that Luke wasn't told the whole truth). She was probably told that Obi-Wan was the potential savior of the Rebellion (which he was indirectly due to his responsibility of watching over Luke).

Given all of this, she was under the impression that Obi-Wan was her only hope. But she wasn't told the rest of the story:

  • Obi-Wan's role as the "hope" for the rebellion was as a teacher, not a leader or warrior
  • The real "hope" was the tag along kid that Obi-Wan brought with him.
  • Through Obi-Wan's (and Yoda's) instruction, Luke would be the savior of the Rebellion
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    The real "hope" was the tag along kid that Obi-Wan brought with him. One might say, A New Hope
    – DickieBoy
    Feb 2, 2015 at 13:07
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    Bail Organa was killed before he could reveal his true reasons for retrieving Obi-Wan. If you imagine Leia arriving at Obi-Wan's home (as opposed to a random Rebel officer), the plan gains another wrinkle: Leia is the one to be trained as a Jedi. Did Bail Organa even know that Luke was on Tatooine?
    – Dane
    Feb 2, 2015 at 14:38
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    @Dane I will have to rewatch Episode III to confirm, but I am virtually certain Organa was involved in the conversation when Yoda and Obi-Wan were discussing where to take Luke as he had just volunteered to take Leia. I do know that Obi-Wan did specifically say something to the effect of "I will take the boy to his family on Tatooine"
    – psubsee2003
    Feb 2, 2015 at 14:41
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    @psubsee2003 - Indeed, Bail Organa was still at the table when Yoda decided that Obi-Wan should take Luke to Tatooine, to his family send him...
    – LcSalazar
    Feb 2, 2015 at 21:17
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    This ain't right. Whatever Bail thought of Obi Wan, it's clear he didn't tell Leia. So Leia's reasons for considering Obi Wan "her only hope" are unrelated to Luke or any prophecies -- they are about the Death Star plans, as she clearly says in her message!
    – Andres F.
    Jul 29, 2015 at 13:48
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My opinion, based purely on the movies and no deep lore knowledge, is:

She is attacked over Tatooine. She has the blueprints, but needs to get them to the rebels. The droids won't be able to do that on their own: they can't realistically be expected to be able to get off-planet. The only person she knows she can trust on the planet is Kenobi.

He's one of the few remaining Jedi, so:

  • probably won't sell her out,
  • more likely than most to heed her call,
  • decent chance of still being alive,
  • probably will have the skills to get the plans where they need to be.

It's still a bit of a long shot. But, given the circumstances, he's her only hope. Nobody else on the planet fits even one of those criteria.

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    Hi and welcome to SciFi.SE. This answer doesn't really offer anything that other answers haven't already mentioned - it's known that Obi-Wan is a trustworthy person to Leia, and it's already been stated that her goal was to get the plans to the Rebels, and that Obi-Wan became her only hope of accomplishing that after her task. This answer would be better as a comment. When you reach sufficient reputation, you'll be able to comment anywhere, and you can always comment on your own posts.
    – Zibbobz
    Feb 2, 2015 at 15:11
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    At the time I wrote, 17 hours ago, before Darth Satan's clarifying edit 16 hours ago, the two other answers appeared to be: she was under attack, so he was "her" only hope (implication: for rescue); and a non-answer responding to the first, about why she went there in the first place, that probably should have been a comment. I reject your evaluation that at the time of my post, giving the correct answer (he was her only hope of getting the plans to the rebels, rather than her only hope for herself) added nothing to the conversation.
    – Dewi Morgan
    Feb 3, 2015 at 0:53
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    +1 I agree with Dewi. One of the other two answers is clearly incorrect, referring to Luke, which Leia didn't even know existed, much less that he was a potential Jedi.
    – Andres F.
    Jul 29, 2015 at 13:50
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    +1. This is the clearest answer to the question. Leia needs somebody to deliver the plans, and Obi Wan is the only person on the entire planet she knows anything at all about. These are the only relevant facts here, and anything else that may or may not be in anyone's minds about Obi Wan's or Luke's capabilities to help the Rebellion later on is irrelevant; they may have driven the decision that brought Leia to Tatooine in the first place, but once that plan failed they became entirely irrelevant.
    – Jules
    May 28, 2017 at 1:33
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Rogue One fills in some of this gap

  • The Rebellion, while it succeeded in getting the Death Star plans, suffered a defeat at Scarif, losing several of their fleet
  • The Rebellion is not united. As we see, there is deep division over whether or not to pursue getting the plans off Scarif
  • Mon Mothma and Bail Organa discuss the necessity of bringing Obi-Wan back

At this point, it looks like the Rebellion will fall apart. The implication of Rogue One is that Leia goes there to find Obi-Wan and bring him back, and thus make him the centerpiece of the Rebellion. If he refused then there was no fallback plan.

From the transcript

MON MOTHMA: Despite what the others say, war is inevitable.
SENATOR ORGANA: Yes, I agree. I must return to Alderaan to inform my people that there will be no peace. We will need every advantage.
MON MOTHMA: Your friend, the Jedi.
SENATOR ORGANA: He served me well during the Clone Wars and has lived in hiding since the Emperor’s purge. Yes, I will send for him.
MON MOTHMA: You’ll need someone you can trust.
SENATOR ORGANA: I would trust her with my life. Captain Antilles, I have a mission for you.
CAPTAIN ANTILLES: Senator.

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According to the original Return of the Jedi novelization, Leia was seeking Obi-Wan because she was told to do so if she was ever desperate.

From the original (pre-SE, pre-prequel) novelization, Ben explains to Luke how they all ended up crossing paths:

"That's what she was doing when her path crossed yours - for her foster parents had always told her to contact me on Tatooine, if her troubles ever became desperate."

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It's possible that Obi Wan Kenobi became her only hope only after the ship was attacked - maybe the only close-by planet with a known ally was Tatooine and she knew that if she deployed the droids there, the information would come to him and he would deliver it to the rebellion.

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Bail Organa knew that most of the Jedi had been killed off during the 19-year Purge. He figured that Obi-Wan might still be alive in his 60s, but that Yoda was extremely old or dead, given his age in 19BBY.

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    Hi Frank and welcome to the site. You seem to be posting one low-value answer after another in quick success. You might want to slow down and try to spend more time on each individual answer. Back them up with some evidence rather than your own supposition.
    – Valorum
    May 12, 2018 at 6:42

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