When Jeremey Bracco had just made an incredible play to outsmart and outskate the Erie Otters to set up the Memorial Cup winning goal, a follower of our Twitter account suggested you package him up with the Leafs’ first-round draft pick and go defender shopping.

While the favourite fantasy trade over the last few months really has been James van Riemsdyk one for one for a defender, with a player that old, that expensive, and that close to UFA status, the one you get back won’t be much.

What about a pick plus a prospect?

When the Leafs acquired Brendan Leipsic, one of the wingers now clogging up the Leafs’ pipeline, that was exactly what the deal was.

Nashville was buying two rentals and dumping a contract in the process, but the deal was the classic first round pick and a prospect. Nashville’s first got turned into two other picks at the draft and one of those was used to select Bracco. The other got turned into two more picks that were used to take Travis Dermott and Martins Dzierkals.

That’s what a smart rebuilding team does, slice a pick into pieces and fill up the roster.

Toronto is on the other side of that kind of deal now. They want more than a one for one deal will get them.

The question is who? Bracco, who is not quite at the same stage Leipsic was when Nashville dealt him, is a name on everyone’s lips. His value might well be a little inflated now. It is with fans, for sure; a lot of them have him in the top nine next season because, wow, did you see that play?

But ahead of Bracco, who has only ever been a right winger, are the two princes: William Nylander and Mitch Marner. And then there’s Connor Brown, Nikita Soshnikov and Kasperi Kapanen.

Bracco has his work cut out for him in the AHL. Ahead of him in experience there are Trevor Moore, Dmytro Timashov, Seth Griffith and perhaps Carl Grundström, who might be moved to the right side at any time because the left is clogged up tight too.

Related 2017 Toronto Maple Leafs depth chart

If there’s a first plus a prospect deal for a really good defender, one worth giving up the pick for, who do you trade away?

Bracco is an unknown quantity; no one can do anything but guess at his professional future. Trading a player when everyone is guessing at his worth is tricky. He might be nothing; he might be the guy deking around your expensive stud defender in the cup final in a few years. His value might be at its highest right now.

Soshinikov has a track record, and it comes complete without much in the way of NHL points. Trading a player who seems to have ‘energy guy’ written all over him is not likely going to make that pick turn into a really good defenceman.

Kapanen has a track record of more scoring ability than Soshnikov, at least in theory, but he also has been busy tailoring his game to the Leafs. He sure looked like a fit for the team this spring. Do the Leafs want to sell the work they put into a player like him? Is he a fit for the team that’s looking?

Brown has an even better track record in a variety of NHL roles, but he’s also 23, like Soshnikov is. Both of those players are less likely to suddenly develop greater heights of talent, but they also still have years at peak playing ability and RFA status to go with their known quantity status.

Every one of these players costs the Leafs something if they lose him. But the easiest player to replace is the one you never had. Bracco doesn’t leave a hole in any lineup and the Leafs have another second round pick to use in a few weeks to add another chance at a future NHLer.

Who do you give up? The truth is likely whoever it takes to get the defender the Leafs want. And that depends on the wants and needs of the team they’re trading with.

I’ve seen fan opinions range everywhere from “trade them all for Hampus Lindholm” to “trade no one, never, ever trade a prospect, and just wait for the magic of development to give you what you need”. Neither of those ideas are likely to succeed.

How do you see this kind of deal working out, or does the idea just fill you with dread that the Leafs might give away one of these players? How high would you bid for the defender you want?