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The Crimson King is clearly written as Roland's enemy throughout the series. However, the man in black has shown to help Roland.

He helps Roland "draw the three" Eddy, Detta (later Susanna), and Jake via drawing three cards. Roland later comes across three doors, each of which ultimately allow Roland to grow a Ka-tet, all of which are clearly enemies of the Crimson King.
Conceivably, the man in black could have let him slowly die by infection on the beachside after the lobstrocities clipped off his fingers without any clue on how to proceed.

Either it was Ka and the Crimson King had no say-so in the matter, but then why would he send the man in black? My question is, why would the Crimson King do anything that would help his enemy?

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    Well, trying not to spolier it too much.... The Man in Black, although perhaps sent by the Crimson King, still had his own agenda and plans, many of which could not occur without much that he, to a degree, facilitated. They cyclic nature of the story also suggests that his actions may have been somewhat circumscribed, and I always wondered if his nature might not have given him some limited insight into the previous iterations. Note: I'm talking about the books - If you are talking about the live-action version, please specify -- it impacts the answers. – K-H-W Oct 27 '17 at 17:53
  • @K-H-W No, I do mean the books. Better I not comment about the movie version since this is a family site. – Neil Oct 30 '17 at 11:37
  • @K-H-W You might be able to flesh out some of these thoughts into a proper answer. – TARS says Reinstate Monica Feb 26 '18 at 0:09
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As is evident from the final book, the Crimson King is quite insane. You shouldn't expect rational explanations for his behaviour.

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    You should merge your accounts, you have thousands of rep (even after the deletion of your original account) and have earned most of the rep privileges. In case you lost the link or forgot how to get there, here's a link to that. Peace out Darth Satan. Darth Melkor, Le thingy whatever, whatever you use on your other sites. – Edlothiad Oct 27 '17 at 17:55
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    This sort of stub answer isn't especially helpful. Can you offer any specific evidence top back it up? – Valorum Oct 27 '17 at 17:55

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