The Portland Trail Blazers had what most would call one of the most spectacular and unlikely seasons in the history of the NBA. The difference between preseason expectations and how things ultimately unfolded was patently ridiculous and amazing and awesome... and well...it’s over now.

As much as this season will stay with me—probably forever—I’m switching over into the offseason and looking forward to what is to come. While some may think that’s too fast, it’s already happening around us: draft combines, camp invites, free agency plans, etc., so it felt like this was the time to lay out how I’m looking at this offseason.

1. A big fish (how big remains to be seen): can they land him?

Are the Blazers invested truly into this core group? Damian Lillard, CJ McCollum and when he returns, Jusuf Nurkic certainly look to be formidable. But are they enough to contend for a title, even if the Golden State Warriors lose some of their star power this season? There’s a strong argument that Portland would still fall short—so who could they add to their roster to bolster their squad? Do the Blazers have the assets necessary to land this player? Are they willing to pay a premium to make it happen, much like the Philadelphia 76ers did for Jimmy Butler?

Is Portland willing to risk the financial viability of the franchise—the ability to build a team that’s even remotely competitive in a couple years if they trade for Blake Griffin? It’s a heavy risk/reward situation.

Here’s where Portland find themselves when it comes to their rotation players and cap space commitments with Damian Lillard, CJ McCollum, Moe Harkless, Zach Collins, Meyers Leonard, Jusuf Nurkic and Evan Turner as their seven key rotation players, and Anfernee Simons, Gary Trent Jr. and Skal Labissiere as their project players.

Which leads us to...

2. Who are the rehab projects?

The Blazers have done a great job at finding and exploiting the margins, with no bigger success than last season there. Just look at Seth Curry, Rodney Hood and Enes Kanter: Curry was picked up as a free agent after being out of basketball for a year. Hood just as may well have been, wasting away in basketball purgatory in Cleveland, and the same could be said of Kanter. They are the exceptions though, not the rule. Rarely will you find high-rotation caliber players in places where you can just pluck them out and add them for little to no cost.

Establishing who those guys are this year becomes incredibly important to the depth of next year’s team. Keep in mind what have been the common threads here: players who have been up and down, shown signs of promise or have fallen out of the rotation, and applying those ideas to players in the soon to be available free agent crop. If you’re keen on adding another point guard type and sliding Simons to the off-guard, perhaps you look at Trey Burke. Troy Daniels, a phenomenal shooter, Alec Burks (who could be much like Hood last year), or if you’re feeling especially lucky, Dragan Bender!

Speaking of feeling lucky!

3. Draft

The Draft is how the Blazers have been built since Day 1. As a small market team on the Northwest frontier, that’s just how it’s always been. Whether or not Portland keeps their pick to add to the cupboard (one that is very bare) or uses it in concert with other assets remains to be seen. If Portland is going to make a move, I would expect it to be early so that it frees up space or allows the next domino to fall into place. Portland isn’t a team that can just hold out until the deadline.

4. Secondary Trades

Making a move around the margin is easier when you have the bodies and assets in place to do so. Right now, Portland has 10 players under contract- 3 of them are Anfernee Simons, Gary Trent Jr. and Skal Labissiere (they combined to play 1.62% of the total available minutes last season). Portland does not have the depth and/or experience on their side right now. If Portland is going to move one of their expiring contracts it has to accomplish a handful of goals: create cap space, bring in talent, and allow for future moves. That’s a tough ask, but those are the waters they have to navigate now.

5. Cap Flexibility (refer to graph above)

This is completely out the window if Portland opts to bring in a top tier asset and switch fully into “go for it” mode. If not, Portland has to be careful how it treats their expiring deals, making sure they are able to get as much capital in return as possible so that they can restock and try again. One thing that Portland has to consider is what Lillard’s supermax deal may or may not mean for McCollum’s future once his contract expires. Asset management will have to be very strict for the immediate future if Portland is unable to get much out of this offseason and a big part of that will be how they manage the cap.

That’s my 30,000 foot view on how I’m looking at this offseason thus far. As the weeks and events progress, I’ll get into more and more detail. Let us know in the comments below what you think—how are you going into this offseason?