As the Leafs prepare to scrap for a playoff spot, the front office has to be simultaneously pleased with the team so far and conscious that the rebuild is entering its crucial second stage.

Rebuilding is a complicated thing, but you can divide it into three rough parts:

Stage One: Tanking and foundational picks

Stage Two: Internal development and secondary additions

Stage Three: Cup contention and complementary pieces

The Leafs are not tanking and they have no realistic hope of drafting in the top five. They have the central parts of their forward group—Auston Matthews, William Nylander, Mitch Marner, Nazem Kadri, possibly James van Riemsdyk—and three key pieces on defence—Morgan Rielly, Jake Gardiner, and Nikita Zaitsev. They also have their starting goalie in Frederik Andersen. All of these players are 27 or younger.

The goal, then, is putting these players in a position to keep growing while surrounding them with additional talent, primarily through trades and free agency—while the Leafs are obviously looking to continue drafting well, they’re unlikely to pick anyone who will provide immediate help. Thus, they have some critical moves to make as they try to rise from fringe playoff team to the league’s elite.

In the next eight months, they will have multiple opportunities to make those moves. This is a look at the four timespans where those opportunities will arise.

January 6th to February 28th: The Trade Deadline

Lou Lamoriello and friends did excellent work in this period last year, executing the masterful Dion Phaneuf trade, the Winnik-for-Laich-and-Carrick deal with Washington, and the transactions with San Jose where we picked up a pair of seconds. The Leafs successfully leveraged their cap space for the 2016-17 season in order to get assets from teams more tightly pressed.

The Leafs still have the cap space to make those kind of deals again, though they’re going to be very leery of taking on any deal with term past 2017-18. Teams may also be less desperate to make cap-dumping trades due to the looming expansion draft—teams can use bad contracts to fill an exposure slot, and maybe even lose them to the Vegas franchise. Still, there’s likely dealing to be done here, if the Leafs want to do it.

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Deadline sales

The Leafs have three players on their NHL roster who are on expiring UFA deals, and they’re probably the three most derided on the team: fourth-line centre Ben Smith and third-pair defenders Matt Hunwick and Roman Polak. Leaf fans will remember Polak was worth (approximately) a second-round pick from San Jose last trade deadline. Maybe a front office that isn’t inclined towards Corsi and wants to shore up its penalty kill would be interested in one of the three.

A more interesting question: would the Leafs want to deal them? I’m not all that attached to this trio, but Mike Babcock clearly is. Considering Ben Smith was on waivers earlier this year and Polak didn’t have the greatest playoff run with the Sharks, it’s possible the return for any of these three would be too low to tempt the Leafs FO into a deal. The Leafs might even seek to upgrade their third pair for a stretch run towards a playoff spot, but the expansion draft makes that difficult (they would be likely to lose whoever they acquired.)

A team might well want a player like Tyler Bozak to shore up its centre depth, but the Leafs are probably too weak at that position to deal him. That leaves a bunch of spare parts like Josh Leivo and Frank Corrado, as well as veteran NHLers-turned-AHLers like Jhonas Enroth, Milan Michalek, Colin Greening, and Brooks Laich. It’s hard to see much of a market for any of these players, and if one exists it’ll be in the Peter Holland range—a conditional late pick.

In short: the Leafs may not want to be sellers, and they probably don’t have much they’re willing to sell.

Cap dumps

As mentioned above, the expansion draft gets in the way of salary dumps of the Brooks Laich variety. Nonetheless, you can point to several capped-out teams whom the Leafs might do business with—Anaheim would love to be rid of Clayton Stoner’s salary I’m sure, and Chicago is paying an awful lot to a defensively solid, but offensively feeble depth C in Marcus Kruger.

In fact, if you squint a little, you can craft some very plausible speculative deals with a lot of teams. In the interest of not being HF Boards, I’ll spare you my elaborate plan where we acquire Kruger and Ville Pokka; the art of this sort of transaction depends on knowing how desperate the opposing GM is. Luckily for us, this has historically been one of Lou’s strong suits, and I would not be surprised to see the Leafs swing a deal of this nature.

April 9th to June 17th: The Expansion Draft

NHL teams will have been maneuvering for the expansion draft during the first period, but once they wrap up their seasons, we can expect a few final transactions. With no more games to play, teams will have nothing else to do but try to minimize their expansion exposure. To take one example, Twitter person you should follow Carolyn Wilke (@Classlicity) has suggested this would be the ideal time for a trade of Marc-Andre Fleury to the Dallas Stars, should Fleury be willing to waive his NMC for it.

What about the Leafs?

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Acquiring exposed players for exempt ones

As currently positioned, the Leafs have more forward protection slots than they need, and if you can envision a team that’s likely to have more forwards than it’s able to protect—for example, Anaheim looks positioned to lose Jakob Silfverberg, and Nashville has too many depth forwards—there might be a deal to be made there. The Leafs also have several expansion-exempt wing prospects, headed by Kasperi Kapanen, who could be appealing to a team caught in this kind of position.

As I’ve written elsewhere, the expansion draft exposes defenders more so than forwards, and here the Leafs have a bit more of a bind—acquiring another expansion-available defender would likely force them to expose Connor Carrick, so it would have to be a definitive upgrade. (Brief reminder—the Leafs are likely to be able to protect three defencemen. Jake Gardiner and Morgan Rielly are obvious choices, and Nikita Zaitsev is exempt. If the Leafs get another d-man, they’ll probably want to protect the guy they acquired with their final protection slot, which means they can no longer use it to shield Carrick.)

Still, if the Leafs see a player they covet at right defence, that they prefer to Carrick, this could be a great opportunity to do it. You can see my look at different defence options here.

June 22 to June 24: The Entry Draft

There’s a short gap between the end of the expansion draft (June 21) and the entry draft (June 23-24). This has the effect of compressing the window for certain trades (the Frederik Andersen trade, for example, happened four days before the entry draft last year.) If you’re trying to build for the future, the draft is where you do most of your work, and the Leafs will have some interesting decisions to make as they work at what’s going to put this team in a position to win.

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Picks for players

The Leafs have two second-round picks this year and two next year. It may seem crazy for a team to transition so quickly from finishing 30th to dealing out of the second round, and the Leafs had better be—and I’m sure will be—very sure before they make that kind of move. But if the Leafs conclude their contention window is poised to open by the end of the decade, they may well decide it’s time to convert one or more of those second-rounders—as they did in the Andersen deal.

Trade-downs

Modern analytics has suggested draft picks decline rapidly in value throughout the first round and level off at a low value thereafter. The rule of thumb is that trading down is usually beneficial to the team trading down after the 24th overall pick or so.

The Leafs have shown a willingness to trade down in the past, although they may be a little more hesitant to do so again after famously trading down from the 24th overall pick in 2015—the pick was used by Philadelphia to draft impressive rookie RW Travis Konecny, while the Leafs return from the deal is encouraging but still tentative at this point. Still, the Leafs have a strong analytics contingent in this FO, and they may conclude that the best move is to maximize the number of lottery tickets. This is a future-oriented move, rather than a present-oriented one, but it may still be the smart strategy.

June 25th to September 10th: Free Agency

While free agency proper begins on July 1st, it’s preceded by a six-day “interview” period where teams allegedly meet, but do not negotiate contracts. Regardless of this bizarre fiction (to judge by the number of deals signed within minutes of free agency opening on Canada Day), the process starts the day after the entry draft, and the Leafs will probably be involved.

Toronto is poised to have a spectacular amount of cap space this summer, as the deals of Stephane Robidas, Brooks Laich, Milan Michalek, Colin Greening, Hunwick, Polak, and Enroth come off the books. With Joffrey Lupul and Nathan Horton ready to be LTIR’d as needed, the Leafs have will likely have $20M or more in cap space, which means they can bid on anyone they want.

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Big-ticket free agent signings

There’s really one major UFA who seems to check all of the Leafs’ boxes, and it’s St. Louis Blues right defenceman Kevin Shattenkirk. I looked at Shattenkirk in great detail in my article on defence signings; suffice to say I want the Leafs to write him a very nice cheque.

The free agent market thins rapidly after that, with most of the big names being very old (for example, Joe Thornton, who is a Hall of Fame centre, but is also 37.) If you look too far past that, you start getting into the dangerous, mushy middle where you pay a spectacular price for a secondary player; this is the the place where the Isles wound up signing Andrew Ladd. Unless Joe Thornton astonishingly wants a one-year deal to be a middle-six C for us, I think the Leafs should be very leery of most of the name FAs.

Small-ticket free agent signings

...but once you get down the list a little, you start finding value again. There are valuable deals to be had towards the low end of FA. The Leafs could use an upgrade at 4C; will Brian Boyle take a two-year deal? The Leafs’ third pair has been a disappointment; maybe Cody Franson or Dmitry Kulikov is worth a look?

It takes a keen eye to sign well out of this market, and the best deals are often signed after the first week—because the prices aren’t driven up by bidding wars. For example, the Columbus Blue Jackets signed Sam Gagner to an absolutely fantastic $650,000 contract on August 1st. It may seem that these are peripheral moves, and they are. But as noted above, the Leafs have many of their key pieces in place; intelligent moves to build depth in July and August may be among the most significant moves the Leafs make for next season.

Major trades

Did you think I’d have mentioned James van Riemsdyk before now? JVR has been in trade rumours for months, as a valuable, but slightly older, star player. A blockbuster trade centering around JVR could happen conceivably at any time, but as we saw last year, the off-season is an ideal time for big moves. Teams have more cap space, they’re restructuring for the future, and they can conduct the trade negotiations before bidding big in free agency. Further, by this point, the expansion draft will no longer be a concern, and whichever team acquires JVR could extent him as early as July 1st.

The Shanahan front office will have to think very carefully about a JVR trade, because JVR is either the Leafs’ most valuable trade chip or a very useful core piece. The Leafs are not especially stacked at left wing—the depth chart beyond JVR runs through puck-retriever Zach Hyman, defensive winger Leo Komarov, physical basher Matt Martin, and AHL agitator Brendan Leipsic—so the loss of JVR’s top-drawer offence would definitely be felt. At the same time, you have to give talent to get talent in trades, and the Leafs definitely want to improve on defence.

Whatever the Leafs do, they’re in a key development phase for the franchise. If Lou is to add a Cup-winning Leafs team to his already proud legacy, the moves he makes in 2017 will be crucial.