Sorry, we can agree to disagree.
Although we can agree that Lou is not even remotely capable of seeing what is best for the franchise long term, he also stubbornly doesn't care about it since he knows; just based on his age alone, that his days are numbered as an operating GM. And yes, that means the likelihood is Nelson will not be traded...but that doesn't mean you should extend him. He is going to stay in "compete now" mode even if it is simply not working with the same ol' gang....
I am totally confused on the highlighted part of your argument as though the two things are dependent upon each other. An extension (especially for 4 years) makes it LESS LIKELY you would even be able to move him anyway should we be out of it- and in my opinion that "likelihood" is a worse risk to take (by extending him) than the possibility of him going elsewhere in 2025. He will be 34 years old then and we should be able to find his replacement rather easily (and remember we have two centers basically locked up for the next half decade in Barzal/Horvat that can be the top two pivots if you have better wings)....
No, sorry it isn't the problem you seem to think it is. It does however become a MAJOR PROBLEM if you are stuck with another Lee-like contract at 7 million per for 4 more years with a player you are hoping is still even remotely as productive in his 34-37 years (slim to no chance)...
Don't do it Lou, please.....