What moves would have to be played leading up to this, obviously both players would have to chip in, but how would this work? Is it even possible to get this board playing with actual rules?
1 Answers
No, on an 8x8 board and the regular American checkers rules, you can capture at most 9 out of the 12 pieces:

The white king can capture here the sequence (in chess notation)
h8 x f6 x h4 x f2 x d4 x b6 x d8 x f6 x d4 x b2
Note that the white king passes the squares f6 and d4 multiple times, which is allowed (what is not allowed, is jumping the same piece more than once).
Because a jumped piece is at least 2 rows and columns away from another jumped piece, it is impossible to add more pieces to this configuration. And because of the board symmetry, it is easy to see that shifting the pieces will also not work.
On a 10x10 board using International draughts rules (where kings can skip multiple empty squares before and after a jump), the maximum you can capture is 19 out of the 20 pieces in the initial position:

Figuring out the correct capture sequence is left as an exercise :-)
Proof game for reaching the second position 1. 31-27 17-21 2. 33-28 21-26 3. 39-33 11-17 4. 44-39 17-21 5. 28-22 6-11 6. 50-44 11-17 7. 22x11 20-24 8. 11-6 12-17 9. 35-30 24x35 10. 34-30 35x24 11. 40-34 7-11 12. 34-30 24x35 13. 39-34 1-7 14. 6-1 8-12 15. 43-39 2-8 16. 34-30 35x24 17. 48-43 14-20 18. 32-28 21x23 19. 39-34 10-14 20. 37-31 26x30 21. 45-40 5-10 22. 44-39 20-25 23. 39-34 30x28 24. 41-37 15-20 25. 37-32 28x37 26. 38-32 37x28 27. 36-31 16-21 28. 31-27 21x32 29. 46-41 18-22 30. 47-42 22-27 31. 41-37 32x41 32. 49-43 24-29 33. 43-39 29-33 34. 39-34 20-24 35. 34-30 24x44 36. 42-38 33x42 37. 1-6 25-30 38. 6-1 30-34 39. 1-6 34-39 40. 6-1 39-43 41. 1-6 27-31 42. 6-1 28-32 43. 1-6 12-18 44. 6-1 7-12 45. 1-6 23-29 46. 6-1 29-33 47. 1-6 19-24 48. 6-1 24-29 49. 1-6 29-34 50. 6-1 14-19 51. 1-6 19-24 52. 6-1 24-30 53. 1-6 10-14 54. 6-1 14-20 55. 1-6 4-10 56. 6-1 13-19 57. 1-6 9-13 58. 6-1 3-9 59. 1-6 19-23 60. 6-1 13-19 61. 1-6 18-22 62. 6-1 17-21 *
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Sorry I'm not familiar with "where kings can skip multiple empty squares before and after a jump" rules, could you explain? – warspyking Sep 14 '14 at 16:32
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@warspyking see e.g. this animated gif on Wikipedia – TemplateRex Sep 14 '14 at 16:41
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So kind of like a bishop in chess? – warspyking Sep 14 '14 at 16:54
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@warspyking yes, jumping bishop – TemplateRex Sep 14 '14 at 16:55
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But the first one is obvious. – warspyking Sep 14 '14 at 17:01
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There is of course a huge caveat here. The contrived board positions shown could not have been reached in regulation play. – MaxW Dec 22 '17 at 18:21
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1@MaxW see the edit with a proof game :) – TemplateRex Dec 22 '17 at 20:38
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@MaxW you can also show that all pieces from the initial position can promote to kings. See one of my other Q&As on this site. – TemplateRex Dec 22 '17 at 20:46