GM's value Brassard more than some here for sure.
The retention hurts trying to trade him for another player coming back, but if it is straight up futures he's bringing back a 1st from a contender.
Just because he's a misfit here doesn't change his value, or the fact a team is going to give him 5.5/6.0 for term next July 1st if not sooner should the team who trades for him doesn't already sign him before then if he wants to be there.
It all comes down to cap hit of the target the Pens choose or are left with from the limited trading partners. Probably 2 to 5/6 teams.
One trade that makes sense is Lowry from the Jets where he is signed for a two years more, but he's not a top six center, but the fit might be there where the cap hits are close. Pushes Little down to 3c. Depth.
This is a trade where the Pens are downgrading due to fit and will most certainly pay more for age, contract as well. There's no need for retention here though.
Jets: Brassard +conditional 3rd: Should Brassard not re-sign with the Jets they receive a 2nd and C level prospect.
for
Pens: Lowry
For a deal around Kevin Hayes... and both being UFA, and only Brassards 3.0 to Hayes 5.175 and age difference
NYR: Brassard + 3rd and 5th
for
Pens: Hayes with retention
Both players probably don't stick with current teams. I know 100% certain Brassard won't.
If it were me, I'd trade him for futures straight up and keep the late 1st and prospect, and then either replace him from within or use the Pens own assets to replace the 3c which should cost way less than a 1st. Two 1sts could come in handy this draft to move up into the high teens. Make up for the 1st and Gustavsson lost getting Brassard. One true time where they could get good assets back.
The Pens have plenty of assets to make that work.