The point was about takng risks. Not about timing and depth. It was still a huge risk to trade those players. You have to take risks to win. In fact the risks taken in '94 may have helped win their last Cup.
Trading for Conolly is an example of a risk it doesn't matter the price or when. This team doesn't have the depth to continue playing it safe or riding things out.
Yes, but risk depends on timing and depth in this case. For example, trading Crosby is a big risk if the other centers a team has behind him are, I don't know, Stepan and Boyle, or equivalent players. Trading Crosby is a lesser risk if a team has Malkin and Staal in line behind him.
It was a risk for Boston to trade those players because they could have, and maybe now have, become better than the guys that Boston was confident could take their spots. But, Boston still had players that they thought could take those spots and play competently. That's an entirely different level of risk than trading players who you have absolutely no replacement for in hopes that adding a winger with no NHL resume will boost scoring enough to offset losing a top pairing d-man.
I'd say the team doesn't have the depth on D to trade a top-pairing d-man to get a winger, which the team has a good amount of right now compared to other assets, including NHL d-men.
Risk is good if it can be justified. Risk for the sake of risk is silly.