We have seen that there is some unspoken hostility between Widmore/Eloise and Richard. When little Ben is brought to Richard, his comment about not needing their approval is part defiant, part cowardly like he wants to get something done with Ben before they stop him.
It was of course assumed that little Ben was taken to Jacob where he was somehow cured but with the side effect of becoming an "Other" permanently. We now know that Jacob lives in the statue and the Temple seems to be the home of the smoke monster. Maybe in 1974, Jacob lived in the Temple and Otherman was trapped in the cabin but since Jacob has been working on that tapestry since Black Rock time, I doubt it.
So did Richard take little Ben to Otherman? Is that where the "loophole" began? If so, what was the loophole? If it's just that a human has to kill Jacob there would be much easier ways to trick any of the people on the island to kill Jacob. Seems like there had to be something special about Ben that happened when he was saved.