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It has been stated that Gandalf had his reasons for sending Bilbo with Thorin & Company. One of them was to prevent an alliance between Sauron and Smaug. However, he also knew that the company was not up to the task of defeating Smaug in combat (his remark about a Hero being unavailable while convincing Thorin to accept Bilbo).

This seems like a contradiction. Gandalf wanted Smaug out of the picture (dead perhaps), but he also set up Thorin's company to steal their wealth from Erebor instead of fighting Smaug.

Did he know that Bard would intervene and defeat Smaug, or have some other hope for Smaug's defeat?

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  • i think he expected that robbing a dragon was impossible anyway, and their mere presence would wake him up, and force the world to deal with him one way or the other.
    – Himarm
    Commented Mar 11, 2017 at 23:47
  • Filling your pockets with gems isn't enough of a plan for you?
    – Valorum
    Commented Mar 11, 2017 at 23:54

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Gandalf likely didn't have a specific plan in mind

He certainly wanted Smaug dead, but his version of the story suggests he was just following his gut, and things just kind of worked out for him1. The most relevant bit of writing comes from Unfinished Tales:

I promised to help [Thorin] if I could. I was as eager as he was to see the end of Smaug, but Thorin was all for plans of battle and war, as if he were really King Thorin the Second, and I could see no hope in that. So I left him and went off to the Shire, and picked up the threads of news. It was a strange business. I did no more than follow the lead of 'chance,' and made many mistakes on the way.

[...]

Suddenly in my mind these three things came together: the great Dragon with his lust, and his keen hearing and scent; the sturdy heavy-booted Dwarves with their old burning grudge; and the quick, soft-footed Hobbit, sick at heart (I guessed) for a sight of the wide world.

[...]

The existence of a secret door, only discoverable by Dwarves, made it seem at least possible to find out something of the Dragon's doings, perhaps even to recover some gold, or some heirloom to ease [Thorin's] heart's longings.

"But that was not enough for me. I knew in my heart that Bilbo must go with him, or the whole quest would be a failure - or, as I should say now, the far more important events by the way would not come to pass.

Unfinished Tales Part III: "The Third Age" Chapter 3: "The Quest of Erebor"

Whether or not Gandalf had a glimpse of the future when making this plan is dealt with elsewhere on the site.

1 We might, and I suspect Tolkien would, consider this an act of Providence

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