Who adds what?
Joined: Jul. 2017
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Beyond a mid-round pick for retention, I don't think you need to sweeten any of these. Teams value puck control. Teams value youth. Teams value draft position and RFA status. Some teams also value size and toughness, but on expiring contracts like Boyle and Simmonds, they're just kind of extra paychecks for teams outside of the playoff picture to write.
Philly can look on CapFriendly and be 100% sure the Caps cannot sign Simmonds for next year. There's just no way they can do it. So even if a team like Colorado offers a 1st pick for Simmonds, Washington doesn't have to match that, necessarily, because Philly can send Simmonds off to play and have fun for the Spring in Washington and then sign him again, long term, on July 1st, to play on a line with Burakovsky. If Simmonds goes to Colorado or Carolina at the deadline, he stays there.