Here's the thing with Gaudreau alot of people have pointed out... Is he really going to want to re-sign here?
So you trade him obviously.
Now, do you do it in the "off-season" or do you do it mid season when the team may be doing well or may not be doing well?
Either way in that last scenario you would be a taking a pretty big risk if you were GM trading a player like Johnny in the middle of a season. This might be the last chance you get in receiving assets while also giving the team a chance to win.
__________________
|