When the judge reviewing the CIA tape destruction says he suspects the CIA duped the court.
This has been going on for a while, and the same song and dance has been played. The Executive Branch office has been saying that the destruction was inadvertent, that they shouldn't have to turn it over, that they were not included in the FOIA request, that the courts and Congress should let the Justice Department (an executive branch entity) do its investigation first, that the dog ate their homework, etc.
The stonewalling has been somewhat effective, but I don't think it's going to last. Again, we're looking at perception. It could be that it was inadvertent that the e-mails were destroyed, but the actions of the CIA, and the fact that so many were destroyed create the appearance of malfeasance.
It's gotten to the point where the judge determining if the CIA should be held in contempt for destroying the e-mails is even questioning whether the CIA was forthright in dealing with the court (a coequal branch of government and certainly a member of the checks and balances that created this Government). Now, I'm just a baby lawyer, but I know that it's not a good thing to lose the judge before the hearing even comes.
Once this comes to fruition, it's likely to be ugly.