Quoting: DeadWingsv2
Because we don't want Kerfoot, or Hollowell, we want decent picks and/or impact players. Even your 3rd is a low 3rd and I don't see that pick having a ton of potential as turning into something valuable anyways. I can see an argument that Merrill might not return a 4th in this season, since he's a bottom pairing guy. We're also not going to retain on LGD. Make it LGD(no retention) and Merrill for a 3rd and a 5th and I'd take that deal. If you want us to take Kerfoot off your hands as a throw in to offset some salary, fine, we'll take him I guess, but that's a throw away to us, not an asset.
You're deal makes sense, but Hollowell is better than a fifth round pick. Besides that, Kerfoot will likely play top 6 minutes in DET. He will get more ice time and opportunity than in TOR, where he is buried beneath all the stardom. You could eventually flip Kerfoot either in the summer or next TDL. It's a save investment with decent volatility but it could work out for a team that needs as many assets as possible.