Regardless of what that nut Jacobs says, if you are a SMART GM, you do your best to make the playoffs while ridding of the least damaging pieces that you can, UNLESS you can make a good hockey trade.
The thing with Chiarelli is that he has to think long and hard about trading away a future piece for a short term solution because 1) It leaves you short in a place where you are already short enough and 2) The piece you're getting back probably doesn't help you a whole heck of a lot at winning a title.
Jacobs' pressure may be on but if Chiarelli and Cam were smart, they'd save their jobs by explaining to Jacobs that this team isn't good enough to make a run, and to get good enough would mean sacrificing very valuable pieces that will be hard to replace and will keep them in the current cap crunch they are in. You make minimal moves here and there, fortify the 4th line, move out some unnecessary cap now.
No need to hold on to guys like Campbell and Paille until the end of the season. If you can move those guys now, do it. Grab a guy like Winnik to replace one of them. Same salary but will give you a change down there that might cause a spark. If it doesn't, you let him go anyway. Try to trim the fat and set yourself up down the road. Look long and hard at guys like Seidenberg, Soderberg, and the like. Are they guys that can still play on the same level they've been at? If not, then move on from them. Get what you can. If you are going to move assets like Subban or another prospect, then package them with someone else to fix that waning piece.
They have to be smart this deadline. Doing something like trading a 1st for Sekera and a 2nd and Spooner for Stewart doesn't make them good enough to win it all, and hurts them in the future as well. They have to manage the cap the right way this time, and make a compelling case to the owner that THIS is the right thing to do long term AND now.