It’s only the beginning of May, but at six weeks out from the expansion draft and everything that immediately follows, it’s not too early to think about this summer’s roster turnover for the Leafs (and everyone else).

The reasons for this being a particularly important offseason for Toronto have been well-documented across a number of sites, but essentially it comes down to some simple points: The first window of contention for this new core is rapidly approaching, there’s some cap room opening up to play around with, and trying to strike while that rookie-turning-sophomore core is cheap should be important for this management group.

League expansion adds an interesting ripple to this whole situation – not in the sense that it presents much of a difficult decision for the Leafs, but because it could make for a lot of moving parts from all over the league. Then we have the regular entry draft, which has typically been a place where blockbusters are worked on. Throwing this Vegas thing into the mix should provide an added shot in the arm. And that’s where we’ll start.

Toronto doesn’t have much to worry about here, at least not relative to the rest of the league. At worst they could lose a player like Carrick, Leivo or Marincin, and at best could see someone like Matt Martin or Eric Fehr claimed. There isn’t any risk of their core group being disrupted, and their key complimentary guys will be safe. Either way, they’re probably in the best position league-wide in terms of exemptions and protections going into this thing, as long as they don’t shoot themselves in the foot [See: Protecting Martin to end up losing Leipsic].

Expansion will surely cause trouble elsewhere in the league though, notably on teams like the Wild and Ducks. I talked about this a while back when discussing the potential of blue-liners like Jonas Brodin or Josh Manson being unearthed as trade pieces. Some general managers could start to lose their minds a little when that expansion draft week rolls around, which could be great for the Leafs in the form of players hitting the block that we weren’t expecting to.

If you look at the timeline for that week in June, you can see how the lid might blow off the league in terms of player movement. Here’s how it’ll shake out:

When you look at it all put together like that, it really does seem like this could be the most exciting offseason in the cap era.

Even without the high pick we’ve been used to seeing the Leafs hold in recent years, the draft should again be interesting. Toronto’s focus on drafting and development in the Shanahan era makes these couple days a good (or bad) time in terms of debate over the team’s approach to bringing aboard new talent, and because we’ve seen them reach to far corners of the planet to do so, it’s usually enlightening as to how the richest team in the league might be extending their resources.

But beyond the picks themselves, this is the floor where many of the biggest deals involving established talent are made. Subban, Weber, Larsson, Hall, Kessel – a lot of those deals were forged at least in part at the draft. If Lamoriello looks to make a major shake-up, this will likely be the best forum to do it. The spillover from the expansion draft just days before will just add to the suspense.

When we talk about the Leafs potentially moving out some of the remaining old core, the draft – or the days leading up – is probably where we’ll see that. That “JVR or Bozak for a defenceman” kind of talk would be applicable here.

The deadline for tabling qualifying offers to restricted free agents is just after the draft and when it comes to the main roster, that’ll mean making decisions on Connor Brown and Zach Hyman. There shouldn’t be anything to worry about there, as we expect both rookies to re-up at reasonable numbers – our own Ryan Hobart tabbed Brown to likely receive 3.0-3.5-million annually in his RFA preview.

Beyond the main roster guys, the Leafs will have to negotiate new deals for AHL players like Brandon Leipsic and Garret Sparks. Those two have futures with the organization so we shouldn’t see anything surprising there. Further down the lineup we could see the team walk away from some others with RFA status, though. Seth Griffith, Justin Holl, Sergei Kalinin, and Antoine Bibeau are all on the fence to varying degrees for qualifying offers.

There’s no Stamkos Fever this go-around, but the free agent market is likely going to present some big decisions for the Leafs, and I expect them to be active. That said, they still could come away empty handed. I’ll explain.

What I’m expecting (or perhaps wishing) for Toronto in free agency is a boom or bust approach. I don’t believe they’ll go the route of adding a new face in the form of a serviceable third liner or a couple fringe defencemen, but instead will put targets on bigger names and try to woo them to joining a team on the rise. It seems nuts to think about the Leafs presenting themselves as a good option for Cup-chasing veterans, but it might be their best strategy.

This upcoming UFA class is relatively weak, but some of the names out there are still intriguing. Kevin Shattenkirk is the marquee of the group, and if Toronto makes a run at him, I think they’d be wise to load up a monster salary on shorter term.

Up front they could take a look at some players with big name recognition in Joe Thornton, Patrick Marleau, or Justin Williams. We can probably throw T.J. Oshie into that mix as well, but at 31, he’s going to look for term that will almost surely turn the Leafs away. Same likely goes for Radulov.

There’s also a few guys that could be on the way out of Hogtown. Brian Boyle, Roman Polak, Matt Hunwick, and Curtis McElhinney are all NHL regulars that have their contracts expiring. Out of that group, I’d expect Lamoriello to try and bring back Boyle and maybe Hunwick if the numbers make sense.

It’s in their buried contracts where the Leafs will see the most significant departures, however, with Colin Greening, Milan Michalek, and Brooks Laich all off the books, representing $8.3-million in cap space. Robidas Island will also be no more, as that $3-million per year goes away.

Going back to the possible additions, we know that in some cases one move will need to spin off from another. Making a play at Thornton as a heavy play-driver for Marner could entail moving out Bozak, for example. And adding a winger would probably result in someone like Hyman or Komarov being put in a weird spot. Let’s remember that Kapanen will almost surely be a Leaf full time next season, and Leipsic likely has nothing left to prove in the AHL either. There’s potential for a lot of moving parts here.

Free agency is also where we’re likely to see Toronto grab another backup goalie if they decide that’s a need. I’m not of the opinion that this is much of a priority – personally I’d run Sparks behind Andersen – but if a veteran with good numbers is there on the cheap, they could pounce.

No doubt this is a bit of a shoot-around topic, but the return of Kovalchuk to the NHL is an interesting storyline this offseason. Toronto probably won’t get him, but since right now no one has any clue where he’s going, I suppose they could be an option. I don’t know what his relationship with Lamoriello is like, but they’re obviously quite familiar with each other from their cap circumvention days, and that has to count for something.

Along with Kovalchuk making his return, some of his KHL teammates are also looking for NHL homes. Yevgeni Dadonov and Vadim Shipachev of SKA St. Petersburg have their own suitors, and we’ve heard rumblings in the past that the Leafs could be among them.

Nothing scientific here, but this is sort of a combination of how I see the existing core of the Leafs right now and what I think the team sees as well. Yes, Martin is not good, but we’ve heard he’s never coming out of the lineup, so I’ve put him in green, meaning basically he’s got that spot locked. The guys I have in yellow also are also established, but I think they’re the three who have the best chances of being trade chips over the summer.

Now before people howl about Hyman and Brown missing, understand that I’m aware those guys are most likely to fill those forward spots again – especially Brown, off a 20-goal rookie season. Marincin and Carrick also have contracts through next season, so they can also be part of the depth on the blue-line if they’re not dealt. I know this. That’s actually the most likely outcome, since nothing is guaranteed in free agency or the trade market.

But this lineup rundown is just used to illustrate where I think the flexibility in the lineup is in terms of potentially making upgrades. I’m not saying these guys are being bumped from the roster, just that those spots in grey-blue would be the ones in flux if we’re looking at movement. The green is essentially the spine of the team, for better or worse.

This isn’t a depth chart.

I mean, Zaitsev is the best RHD the Leafs currently have, but it would probably be ideal to plug Shattenkirk or whoever into that spot ahead of him. We assume Hyman, Brown, and Kapanen should all be able to make the team again next year, but maybe there’s some jostling around there. Could someone like Justin Williams or Patrick Marleau step in and play with Matthews or Kadri and push someone down? Of course. Maybe Bozak gets moved out or down, and Joe Thornton steps in alongside Marner. These are probably the types of moves that become available to Toronto if they decide to try and round out this roster with veterans to make a run next season.

And maybe none of that materializes, which would probably be fine. But it’s undeniable that the Leafs are looking at a window approaching where they can do a lot of damage while their kids are cheap, and they know it. This summer is unique in its inclusion of an expansion draft, and the flat cap adds a level of intrigue again. Toronto doesn’t have to be stupid and over-step their plan by any means, but I certainly wouldn’t bet on them standing pat.