I don't recall the backstory, but surely Kindler must have inherited his wealth. He's not even clever enough to recognize "good cop" (although the phrase doesn't really apply here ).
Maybe the torture is affecting his thinking?
Kindler's backstory has unfortunately never really been covered, but it was very much a right-time/right-place kind of thing. His fortune came from steel processing. Whether he'll be able to keep Kindler Airlines operating in the long run is another question.
One thing that has been discussed before, though (a loooong time ago), is his penchant for whiskey regardless of circumstances: http://johnwallie.com/Sunrise/2008/05/27/issue-1-...
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