Before I proceed with whether the Flyers should sign or trade Simmonds, the first underlying issue that needs to be identified is whether the Flyers value Simmonds as part of the leadership core with his character and style of play to make a multi-year commitment.
There are a handful of championship-caliber teams that desperately need Simmonds' toughness and grit, not to mention how he plays around the net. However, Simmonds has been part of the Flyers' cog for eight seasons now and it's worth taking a hard look at the construction of this team and whether it has the right blend of talent and leadership.
With Claude Giroux, Jakub Voracek and now James van Riemsdyk all under contract for several more seasons, I contend that the Flyers can't bring this core group back next season. It's not working. They haven't advanced in the Stanley Cup Playoffs since 2012, and those key players I mentioned aren't getting any younger. This isn't like the San Jose Sharks in 2016 when they finally had a breakthrough, reaching the Cup Final after so many years of coming up short.
Simmonds brings a unique skill set that is increasingly becoming rarer to find in this league, but I also realize he's a defensive liability with a minus-50 rating since 2016. He's not the most defensively responsible forward on the team and the Flyers don't have very many two-way players at the forward position.
If I'm general manager Chuck Fletcher, I simply can't go longer than a three-year extension with Simmonds. Part of the issue over the past seven to 10 years has been locking up players with long-term contracts and then paying the price for that extended term down the road. If Simmonds doesn't accept a short-term offer, then trading him before the deadline would only make logical sense.