The hubbub over the "torture memos" - and particularly Judge Jay Bybee's defense of the memos he signed - illustrates a legal counseling issue deeply familiar to any corporate general counsel: A leader looking for an aggressive interpretation of existing law to support a planned course of action.
Second-guessing by ivory tower types aside, there's little doubt that the memos represent a legally-defensible interpretation of the state of the law in this area. However, in a well-functioning organization, with a strong GC and open communication, the memos would go beyond discussing the outer bounds of what is permissible under the rules to point out the potential downside versus the limited utility of these methods of interrogation.
Bybee's fault is that he's too much of a lawyer's lawyer, providing only the legal analysis and not wading into the risk/reward and policy analysis (to quote from his memo: "This memorandum expresses no view as to whether the President should decide, as a matter of policy, that the U.S. Armed Forces should adhere to lhc standards of conduct in those treaties with respect to the treatment of prisoners"). And of course, he worked within a tremendously dysfunctional structure not noted for its openness.
It's regrettable he couldn't be more of a leader at that uncertain time. However, while you might not want Bybee to be providing strategic guidance to your organization, he's certainly no criminal.