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I also agree with the prior posts. But, if forced to modify (minimally invasive) the current sentence, I might change it to:
"Bill was not the brightest of men, and in late night drunken monologues delivered to his son, he would often relate bitterly how in hindsight he could have perhaps chosen a better target."
I think that resolves the ownership problem, but I'll defer to the more experienced on the board to correct me, if I'm wrong.
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