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edited Jul 16, 2020 at 8:40

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He didn't know or care about it.

The Shire was a small entity within the realm of Arnor (or Arthedain), not politically or militarily powerful. We know that it and its inhabitants were very little known except by its nearest neighbours (the men of Bree, or the Rangers of the North) and a few of the Wise such as Gandalf who understood the virtue of humility. There's no reason to think the Witch-Kingking even knew about the Shire's existence, much less bothered to conquer it.

It was only after the fall of Arthedain in T.A. 1974 that the Shire became an independent organised political unit, appointing the first Thain in T.A. 1979. By that time, the Witch-Kingking probably thought he'd already consolidated his power in all the parts of Arnor that mattered, and wouldn't even notice some little people organising themselves in a little place on his borders. At the time that he was bent on conquest, there wasn't even a Shire as such, just some hobbits.

In fact, when the Ringwraiths began their search for the Ring after Gollum gave information to the servants of Sauron, they didn't even know where in the world to look for hobbits! Their search began near the Anduin, on the wrong side of the Misty Mountains, because that was where halflings (Stoors) had lived centuries before:

About the twenty-second of July [3018] they met their companions, the Nazgûl of Dol Guldur, in the Field of Celebrant. There they learned that Gollum [...] had vanished. They were told also by Khamûl that no dwelling of Halflings could be discovered in the Vales of Anduin, and that the villages of the Stoors by the Gladden had long been deserted. But the Lord of Morgul, seeing no better counsel, determined still to seek northward [...]

_{-- Unfinished Tales, Part 3, Chapter 4: "The Hunt for the Ring" (emphasis mine)}

This shows that the servants of Sauron, even the Witch-Kingking who knew the northern Arnor region well, didn't even know that hobbits lived up in that part of the world! If he ever knew about the Shire on his borders, he cared so little that he'd forgotten by the time it was important.

_{Similar question on Quora, whose answer helped me in composing this one.}

He didn't know or care about it.

The Shire was a small entity within the realm of Arnor (or Arthedain), not politically or militarily powerful. We know that it and its inhabitants were very little known except by its nearest neighbours (the men of Bree, or the Rangers of the North) and a few of the Wise such as Gandalf who understood the virtue of humility. There's no reason to think the Witch-King even knew about the Shire's existence, much less bothered to conquer it.

It was only after the fall of Arthedain in T.A. 1974 that the Shire became an independent organised political unit, appointing the first Thain in T.A. 1979. By that time, the Witch-King probably thought he'd already consolidated his power in all the parts of Arnor that mattered, and wouldn't even notice some little people organising themselves in a little place on his borders. At the time that he was bent on conquest, there wasn't even a Shire as such, just some hobbits.

About the twenty-second of July [3018] they met their companions, the Nazgûl of Dol Guldur, in the Field of Celebrant. There they learned that Gollum [...] had vanished. They were told also by Khamûl that no dwelling of Halflings could be discovered in the Vales of Anduin, and that the villages of the Stoors by the Gladden had long been deserted. But the Lord of Morgul, seeing no better counsel, determined still to seek northward [...]

_{-- Unfinished Tales, Part 3, Chapter 4: "The Hunt for the Ring" (emphasis mine)}

This shows that the servants of Sauron, even the Witch-King who knew the northern Arnor region well, didn't even know that hobbits lived up in that part of the world! If he ever knew about the Shire on his borders, he cared so little that he'd forgotten by the time it was important.

_{Similar question on Quora, whose answer helped me in composing this one.}

He didn't know or care about it.

The Shire was a small entity within the realm of Arnor (or Arthedain), not politically or militarily powerful. We know that it and its inhabitants were very little known except by its nearest neighbours (the men of Bree, or the Rangers of the North) and a few of the Wise such as Gandalf who understood the virtue of humility. There's no reason to think the Witch-king even knew about the Shire's existence, much less bothered to conquer it.

It was only after the fall of Arthedain in T.A. 1974 that the Shire became an independent organised political unit, appointing the first Thain in T.A. 1979. By that time, the Witch-king probably thought he'd already consolidated his power in all the parts of Arnor that mattered, and wouldn't even notice some little people organising themselves in a little place on his borders. At the time that he was bent on conquest, there wasn't even a Shire as such, just some hobbits.

About the twenty-second of July [3018] they met their companions, the Nazgûl of Dol Guldur, in the Field of Celebrant. There they learned that Gollum [...] had vanished. They were told also by Khamûl that no dwelling of Halflings could be discovered in the Vales of Anduin, and that the villages of the Stoors by the Gladden had long been deserted. But the Lord of Morgul, seeing no better counsel, determined still to seek northward [...]

_{-- Unfinished Tales, Part 3, Chapter 4: "The Hunt for the Ring" (emphasis mine)}

This shows that the servants of Sauron, even the Witch-king who knew the northern Arnor region well, didn't even know that hobbits lived up in that part of the world! If he ever knew about the Shire on his borders, he cared so little that he'd forgotten by the time it was important.

_{Similar question on Quora, whose answer helped me in composing this one.}

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created Jul 16, 2020 at 7:32

Rand al'Thor ♦

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He didn't know or care about it.

The Shire was a small entity within the realm of Arnor (or Arthedain), not politically or militarily powerful. We know that it and its inhabitants were very little known except by its nearest neighbours (the men of Bree, or the Rangers of the North) and a few of the Wise such as Gandalf who understood the virtue of humility. There's no reason to think the Witch-King even knew about the Shire's existence, much less bothered to conquer it.

It was only after the fall of Arthedain in T.A. 1974 that the Shire became an independent organised political unit, appointing the first Thain in T.A. 1979. By that time, the Witch-King probably thought he'd already consolidated his power in all the parts of Arnor that mattered, and wouldn't even notice some little people organising themselves in a little place on his borders. At the time that he was bent on conquest, there wasn't even a Shire as such, just some hobbits.

About the twenty-second of July [3018] they met their companions, the Nazgûl of Dol Guldur, in the Field of Celebrant. There they learned that Gollum [...] had vanished. They were told also by Khamûl that no dwelling of Halflings could be discovered in the Vales of Anduin, and that the villages of the Stoors by the Gladden had long been deserted. But the Lord of Morgul, seeing no better counsel, determined still to seek northward [...]

_{-- Unfinished Tales, Part 3, Chapter 4: "The Hunt for the Ring" (emphasis mine)}

_{Similar question on Quora, whose answer helped me in composing this one.}