One Stop Shop

I question whether Murphy is a significant enough upgrade over Holl considering how well Holl has played this year, to be spending so much money and assets. Then with that saved 2.4M + Send down Benn and Timmins/Malgin, you have room to keep Kerfoot too.

I'm all for going for it this year, this team is elite. But, it's a lot to give up, and the core is still young - I'd stick to moving only one 1st and one top prospect this year, so you can load up again next year and so forth. Get one impact forward, maybe another cheaper forward if its there at a reasonable price, and a bottom pairing D to be the 7th D. Can't be giving the whole farm for one year

Hawks decline. Short at least another 1st or another really high end prospect. Even w/ Murphy and Holl removed from the trade, Hawks probably still decline (although that would be a lot closer).

AZ gets more than that to take up both it's remaining retention slits

You can't send down Timmins because he has to clear waivers. I don't think he will and he has played really good and looks like a future full time d-man.

Murphy doesn't improve the Leafs this year by trading Holl, really his 4.4m cap for the next three years isn't that great.
Then to give up all those picks and prospects for two rental. One is 3rd line centre and the other has four goals this season.. Yeah the Leafs would be better this year the forward, but it's a steep price that no other team in the league would offer.