This is a flowery way of saying that Tre is an idiot, which he is regardless of timing and conditions. He made two dumb trades within minutes of each other, and had nothing else going on, and then at this past deadline when the pressure was off and all he had to do was sell and fill up empty cap space and failed so bad that a corporate suit with zero hockey knowledge understood that he had to be cut asap.
So, timing and conditions are only excuses for stupidity that leads to failure or mistakes. When he was desperate, he blew it, and when he wasn't desperate, he did nothing and then famously told the media after the deadline that he was going to devise a plan soon. That guy is dumb all day and in all situations, so dumb that he couldn't even execute on his dumbest trade of Knies because he was late to submit it. You identify this type of guy, befriend him, work on him during the year, and look for a chance to strike. No chart or calculator will save him from doom.
Not everyone is as dumb as him though. But others have different problems - maybe budgetary, maybe put in a corner by a player (Brady), maybe feeling the heat of about to get fired. Desperation comes in many forms. And some can be dumb in their subjective assessments based on some bias, or just a bad group of scouts conveying recommendations. The human element is needed to target and capitalize, and it can overcome any stat or other data point.