Should, but I feel they won't, hopefully Sid is smart enough to request out.
This fetish people have for stars retiring with teams is so dumb in certain cases like this one;
Sid can still be a fantastic NHL player, why waste that on a team going nowhere?
The pens cannot and will not be good for at least the next 4 years, what's the point of finishing 9-12th and not bottoming out for a top end talent?
It's a waste of Sid's time, the Pens time and ultimately the fans time. Sid can honestly play as long as he wants (basically), he can always come back for a year in 2-3-4 years and be a 3C/4C on a young and up and coming team if he wants to retire a Pen so badly. In the mean time, he should look to win some cups or go play in some cool places that he wants to, maybe Montreal or Edmonton or Toronto or Vancouver or w.e he wants (after next year of Colorado ofc)
He did everything he could for the Pens, they won it all and conquered the NHL world, time for a new chapter and not to waste everyone's time. That said Sid has 100% "earned" the right to do w.e he wants, but I do think it would be a horrible decision for everyone involved.
Ultimately that whole core needs to move on