As much as Simmonds has meant to the club, it would be foolish to lock in with him for extended term. More than 2 years, MAYBE 3, would be a problem.
And for as much as this team may mean to Simmonds, it would be foolish of him to not take care of his financial future in this last, real contract of his career.
Someone will offer a JVR type contract. It should (will?) not be the Flyers. And Wayne should/will take it.
As to trading him now, there is one major difference between me and Hextall - ignoring his fame and fortune and my stunningly great looks - and that is he need s to find out whether Hakstol can take this team to the next level. He now has a team to prove he can do it, and is in the penultimate year of his contract. Hextall will not trade Simmonds unless the team falls apart, at which point Hakstol has punched his ticket out of here, but Hak will be given the opportunity to show that he can do with a young, promising and somewhat established d, a solid set of forwards, and a mediocre goaltending tandem.