Using your scenerio (not booking when space is available to book) what would you tell a passenger standing in front of you? And the guy behind him and so on, as I'm sure the lines are dozens deep. If space is available, use it. And let's get to the real problem. It's other airlines booking these people on WN. "Evidently, all the overflows from other airline cancellations are coming into Southwest". Those are the OP's words so other airlines are booking them and they are coming. What is WN's fault is them not being proactive after seeing what was happening is cutting off the overbooking. Maybe it happened to fast or who knows but they should have seen this coming and done something about the overbooking levels. That part I will blame them for.
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