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As we know Gandalf had a far bigger plan than the dwarves when he decided to join their quest of reclaiming Erabor. Smaug, the dragon, was always on his mind, and he feared that Sauron would gain control over it. This would be catastrophic for the good people of Middle Earth as it would lead to 2 (possibly 3, if we include Isengard) fronts in the great war.

My question is however, how did he plan to kill Smaug? He surely couldn't count on Bard hitting the dragon with one black arrow (or predict that the dragon would go to Laketown in the first place).

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    His plan was one exercised by all great leaders: find a team of intelligent, driven followers and let them solve problems. Make sire one of the team is a thief.
    – DVK-on-Ahch-To
    Jan 13, 2014 at 16:49
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    Gandalf knew that once you start a children's book with 13 cute characters, you can't end it by having them all eaten by a dragon.
    – Oldcat
    Jan 14, 2014 at 1:57
  • @oldcat I wouldn't mind a few dwarves getting eaten, though...
    – Jamin Grey
    May 11, 2017 at 20:08

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All the evidence points to him having no plan. The Quest of Erebor, in Unfinished Tales, outlines his thoughts leading up to and shortly after his first meeting with Thorin, and there is no indication whatsoever that he had any plan for how smaug must be dealt with.

As he says himself in the narrative:

So it was that the Quest of Erebor set out. I do not suppose that when it started Thorin had any real hope of destroying Smaug. There was no hope. Yet it happened.

This may seem unlikely, but it's actually fully in line with the remit of the Istari: to inspire, but not to act directly themselves. From the Istari essay (again in UT):

(They) were forbidden to reveal themselves in forms of majesty, or to seek to rule the wills of Men and Elves by open display of power, but coming in shapes weak and humble were bidden to advise and persuade Men and Elves to good.

So his part in the Quest would be to get it started, to get Bilbo involved in it, and to help it along the way (up to a point), but the actual business of killing Smaug would be something he would have left to those he inspired.

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    I don't have any textual backup, but I do wonder how much of his actions here were inspired by knowledge he wasn't allowed to consciously access as a Wizard, but did have as a Maia.
    – Daniel Roseman
    Jan 13, 2014 at 18:01
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    @DanielRoseman - Gandalf's "If this hobbit goes with you, you will succeed. If not, you will fail. A foresight is on me, and I am warning you" suggests that some was, but it may have been a vague-ish intuition rather than specific knowledge.
    – user8719
    Jan 13, 2014 at 18:22
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Dragons had been fought and slain before. Typically not by armies, but by individuals or small parties. I'm sure Gandalf didn't have an exact execution plan, but instead trusted in the Valar to guide them in their struggle against Sauron. This might be an instance of the act of resistance being more important than the precise execution mechanisms. An example of faith perhaps.

This is subjective, but it might also be possible that he used the Dwarves' greed to act as a catalyst to motivate the armies of men and elves to take out a great potential ally of Sauron.

http://tolkiengateway.net/wiki/Dragons#The_origin_and_early_history_of_dragons

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