Quoting: GMTD
I think that is just about the right price for one year of a cap dump. Other players were traded with first round picks had a much longer term. For example I have seen Lucic traded with a first, I would do this trade.
In addition Callahan would add leadership and playoff experience.
This is the type of trade that Betterall would make for the long term and receive benefits next year.
1)Lucic team's 1st rounder would be number 8 overall (netting a very good prospect Krebs, Zegras, or Podkolzin) and has much more value than a low 2nd round pick where the guy is more likely than not never going to make it above the 3rd line/role player status. Beyond that no one is taking on Lucic's contract for only 1x 1st round pick. Just because an idiot on here says it won't make it happen.
2)No one interested in acquiring Callahan's salary needs him for playoff experience/leadership traits. They are taking on the contract to get prospects/picks. An added benefit is that he can teach their young players how to be a professional, but that is no where near why he is being acquired. Since he doesn't possess a full NMC he can be traded without his approval and would be an UFA afterwards--meaning he wouldn't stay beyond the 1 year anyways (and probably would get moved again at the trade deadline).
3) Simmonds is not going to take the risk on a 1 year deal given his injury history:
2018 torn pelvis, pulled groin, broken teeth from Mattias Ekholm’s stick, breaks ankle on Shayne Gostisbehere snapshot, another broken tooth, tore ligament in thumb.
2019 missed final 4 games of the playoff series after upper body injury in game 2.
He's a bottom 6 forward at this point in his career and will want security to balance injury risks on how he plays.