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Step By Step Through the Trail Blazers Decision Tree

Every inflection point for Portland this summer laid out and explained,

Detroit Pistons v Portland Trail Blazers Photo by Amanda Loman/Getty Images

The Portland Trail Blazers have a long road ahead of them in the Summer of 2023 if they want to transform from their current 33-win status into a contending team, fulfilling the promise they’ve made to superstar Damian Lillard. The process will not be simple.

The Blazers have specific tools to employ at given stages of the off-season, while others will be denied to them, or at least muted in a competitive disadvantage to other franchises.

This post will lay out the steps and decisions points the Blazers will face in their quest to build, in roughly chronological order. You might want to bookmark it for reference as the summer unfolds.

If you haven’t already listened to our year-end podcast on Portland’s situation, you can find it here. It spells out some of these items in a conversational manner, plus a few tidbits besides.

Step 1: Where Does the Lottery Pick Fall?

The 2023 NBA Draft Lottery will be held on Tuesday, May 16th at the Barclays Center in Brooklyn. This will be the first major inflection point for the Blazers. They earned the fifth-worst record in the league this year, giving the following lottery odds for each pick:

  1. 10.5%
  2. 10.5%
  3. 10.6%
  4. 10.5%
  5. 2.2%
  6. 19.6%
  7. 26.7%
  8. 8.7%
  9. 0.6%

As you can see, it’s likely Portland will get either the 6th or 7th selection (46.3% total chance) but it’s also quite possible they’ll advance to the Top 4 (42.1% total chance). Those six spots encompass 88.4% of Portland’s probability.

No matter which selection the Blazers get, they have two options: use it or trade it.

If the Blazers receive the first overall pick, the discussion is over. Like every other team in the league, they’d select French center Victor Wembanyama.

Wembanyama has the disadvantage of being one of those 19-year-olds that Damian Lillard said he wasn’t interested in adding to the team during his exit interview following the season. But he has the distinct advantage of profiling as a generational superstar with every bit as much impact as Lillard himself. If Wembanyama were the teenager in question, Lillard would probably change his tune. If he didn’t, the Blazers would likely override his objections, anticipating the worst outcome as rebuilding around their new talent while trading Dame for even more future assets.

Between Wembanyama, Shaedon Sharpe, and Anfernee Simons, a 2023 lottery win would yield a roster revolution every bit as significant as Brandon Roy, LaMarcus Aldridge, and Greg Oden did in 2006 and 2007, hopefully with a better outcome.

If the Blazers end up in the 6th or 7th spot, the outcome is also clear. They lucked out with Sharpe last season via the 7th pick, but he’s not ready to play on a contending team yet. There’s no guarantee they’d get that kind of talent again from a similar position. If they did, the learning curve could take just as long. Because of the Lillard Mandate, that’s time they can’t afford.

Falling to the mid-lottery, Portland would try to use the pick as one of the tent poles in their quest for a Three Ring Circus deal to alter the course of the franchise. (More on that soon.)

The Blazers will face an interesting decision if they get the 4th, 3rd, or especially the 2nd selection. Those are expected to yield excellent players, but they also increase Portland’s trade capital correspondingly. Having publicly vowed to build a quick contender around Dame, they’d likely view trading the pick as a first option. If they could not find a fantastic deal, they’d need to think about using it. There’s no guarantee they can win a ring with Lillard even under ideal circumstances. Coming off of 33 wins, they can’t trade away a potentially great player later for a merely good one now. It’s not just that the swing wouldn’t be good; they might not even get out of the on-deck circle.

Step 2: Appease the Bulls?

There’s another little hitch in the giddy-up. The Blazers still owe the Chicago Bulls a conditional first-round pick as payment for the Larry Nance, Jr. trade in the summer of 2021. Nance is long gone, but the debt remains, as the pick was lottery-protected. Since the Blazers were in the lottery last year and returned this year, Chicago remains unsatisfied.

The Blazers are holding the 23rd overall pick in this year’s draft, though. They got that from the New York Knicks in exchange for Josh Hart in February.

Technically, that Knicks pick doesn’t belong to Chicago, as the deal was for Portland’s own non-lottery pick, the first one available between 2022 and 2028.

The Blazers and Bulls can come to an agreement to use the 23rd pick in payment for the debt, though. In essence, Chicago would trade that future (owed) pick back to Portland in exchange for Pick 23 this year. The Bulls would have their first-rounder and the Blazers would be free of the obligation.

Why is this important? Because picks potentially owed to another team in the future cannot be used in trades, at least not without putting even more conditions on the deal and compounding the problem. Nor can teams make trades that would leave them without first-round picks in consecutive future years. As long as Portland owes this pick, using first-rounders in trade becomes complicated.

If Chicago would agree to take the Knicks pick as satisfactory compensation, the Blazers would free up all of their future firsts to use pursuing the Big Daddy deal they need to reinvigorate their lineup. (More on that soon.)

If necessary, throwing cash or a future second-rounder Chicago’s way to sweeten the incentive might be prudent. That said, the Bulls don’t have a first-rounder this year. Next year’s draft is not expected to be deep. If the Blazers make the playoffs in 2024, the 23rd selection this year may yield better talent than whatever pick they’d get next summer. Therefore they may jump at the opportunity without enticement.

Step 3: Which Free Agents Come Back?

A full salary cap rundown for the Blazers would be its own essay. We’ll give you a detailed breakdown before July, but for the purposes of this post, here’s what you need to know.

  • The NBA salary cap for 2023-24 is expected to be $134 million.
  • The Blazers have approximately $110 million in current salary obligations for 10 players, very little of which is disposable. They also have around $4 million in “dead money” obligation to players now departed who still count towards the cap ledger. That totals $114 million, leaving roughly $20 million available.
  • The following players are not covered by that figure: Jerami Grant, Cam Reddish, Matisse Thybulle, Justise Winslow, Drew Eubanks, Ibou Badji, John Butler, and Portland’s first-round lottery selection in the upcoming draft. (The Knicks pick isn’t either.)
  • In order to generate that $20 million in usable cap space (which would really look more like $18 million after incomplete roster charges), the Blazers would have to relinquish their rights to all of the above. If they don’t waive all those players, the cap hold on the lot would total $80 million, obliterating Portland’s space to sign free agents.

Since there’s no way the Blazers would waive Jerami Grant, let alone all of those players, just to generate $18 million of cap space to sign an upper-mid-tier free agent, Portland will have zero cap space to work with in July. They’ll probably have a mid-level exception of around $11 million and a bi-annual exception of $4.5 million. That’s it as far as outright signings.

That does leave the Blazers with an interesting question: Which of their own free agents will they try to retain? The answer to that may depend on a critical follow-up question: Are they willing to go into the luxury tax next season?

The luxury tax threshold for 2023-24 projects at $162 million. Remember, Portland has $114 million or so in hard-to-dodge obligations already.

Grant is the most obvious target for re-signing. He’s rumored to be up for a $30+ million annual salary. It’s impossible to account for all possibilities, but it’d be reasonable to expect Grant’s contract to cost Portland $28 million next year. (The balance of the average would come via raises in subsequent years.)

$114 million plus $28 million makes $142 million in salary.

Cam Reddish and Matisse Thybulle have qualifying offers of $7.7 million and $6.3 million respectively. If the Blazers retained them, they’d add $14 million to the $142, making $156 million.

The 6th or 7th pick in the draft, if retained, would cost $5.5-$6 million, putting Portland right at the tax threshold. A higher pick would cost more, up to $9 million for the first overall pick.

As you can see, the lottery rookie would eat up the remainder of the Blazers’ room under the tax threshold, or might even cause them to exceed the barrier.

They do have options to avoid this. They could trade the pick, obviously, and plenty of other players on the roster besides.

Failing that, they could stay away from the tax by letting Thybulle or Reddish go, perhaps keeping a cheaper player like Winslow in the stead of one of them.

The Blazers could also opt to start the season over the threshold, depending on mid-year trades to bring them below. Salaries are not counted for tax purposes until the end of the season.

Or the Blazers could say, “To heck with it!” and just go into the tax. The problems with that approach are two. First, their current record doesn’t justify it. Second, the players they’re retaining aren’t likely to give them enough of a boost to change that story.

For those reasons, it’s likely that Portland will try to stay below the tax unless they’re presented with a no-brainer deal that would propel them over as the inevitable cost of leaping into clear contention.

If the Blazers do want to stay out of the tax, they’re going to have to be selective about who they keep this summer after the presumably-obligatory Grant signing. It’s getting harder to make bald salary-dump deals, as more and more teams are exceeding the cap. Of 30 NBA franchises, only one—the San Antonio Spurs—retained meaningful cap space this season. You may seem them pass over some of their incumbent players to avoid the whole conundrum.

Long story short, it’d be a major shock if Jerami Grant isn’t inked to a new deal early in free agency. His cap hold of $31 million exceeds his projected salary and the Blazers can’t possibly replace him with the money they’d save by not re-signing him. If Grant doesn’t sign immediately, that’s not good news.

Presuming the Blazers and Grant do come to an agreement, it’ll be super interesting to see which other players they try to re-sign. They’ll need to walk a tightrope between maximizing bench talent, avoiding exorbitant costs, and leaving themselves flexibility in future deals through the season so they’re not forced to lose players mid-season (or forego trading for them) simply to save money.

Step 3A: Use Cap Exceptions?

As mentioned above, the Blazers could have up to $15 million in cap exceptions available to sign free agents this summer. These are bonus coupons, allowing a team to sign a roving free agent even if the team is over the cap and doesn’t have money to do so organically.

After the explanation about the luxury tax just above, it’s easy to understand why they’ll probably think twice before using those exceptions.

This will probably be a minor matter compared to the other decision points, but it might make sense if the Blazers opt against re-signing one or more of their current players, instead using their exception to sign a non-incumbent free agent with that money.

Using their exceptions might also make sense if the Blazers go into “talent at all costs” acquisition mode and blow past the tax threshold.

Either way, it’ll be easy to see the costs and benefits of these exception-related decisions as they happen.

Step 4: The Big Trade?

Having gone through all those steps, we can now admit that this is where the summer is headed.

With Damian Lillard demanding action, General Manager Joe Cronin promising the franchise’s priority is to contend, and the team needing serious help in order to make either manifestation even close to reality, the infamous Big Trade has become the new Portland mantra.

A move could happen before the draft, on draft night, or after free agency opens in July. Either way, a swing for the fences on the trade market remains Portland’s best non-Wembanyama chance at relevancy.

It’s worth noting once again the conditions that make this necessary:

  1. If this year’s results are any indication, no incremental move is going to revive this franchise quickly (or far) enough. They’re now to the point of needing something dramatic.
  2. The Blazers have no money to spend on free agents.

Here are the critical sub-questions governing trade decisions.

What Assets do the Blazers Have?

Assuming the Blazers will not trade Lillard—which would make the quick rebuild no longer necessary—they will be offering young talent and draft picks.

First-round picks are conditional on freeing up obligation to Chicago, as described above. If the Blazers do that, they have their full suite of current and future picks to deal. That’s a strong position.

The caveat here is that draft picks don’t seem as valuable in the current market as they were a few years ago. First-rounders were once prized as the way to find hidden talent at a cheap price. In 2023, scouting is so pervasive and ubiquitous that “draft steals” are harder to find. The salary cap is rising annually, sometimes dramatically, with broadcasting windfalls. This gives teams more money to spend overall. In addition, almost all teams have gotten better at managing the cap, fully comfortable operating in the zone between the cap and tax. Saving a couple million on the roster doesn’t mean as much as it used to.

A high lottery pick will always spend. They’re the gold standard. But lower-level picks are coming closer to cryptocurrency: traded for established players and accumulated, not just to use, but to “bank” and turn around for other established players in future swaps.

We saw some of the effects of this at the 2023 NBA Trade Deadline. Second-round picks flowed like water, a half-dozen per trade. The Toronto Raptors reportedly turned down three first-rounders for OG Anunoby.

We’ll not overstate; draft picks are still an effective enticement. But their quality and purpose matters as well. They’re no longer an automatic gate to Trade Paradise.

Fortunately, the Blazers also have a pair of young guards in Anfernee Simons and Shaedon Sharpe to offer. Expect those names, singly or in tandem, to lie at the heart of trade talks this summer.

The Blazers would probably be willing to include Jusuf Nurkic alongside for salary and talent purposes. His $16 million contract makes a nice bridge between young players and veteran salaries.

Grant has been brought up as a potential sign-and-trade, but accepting that kind of deal hard caps the receiving team, so there are complications.

That talent pool is not overwhelming, but it’s not bad. The Blazers have the ability to make an attractive offer.

Who’s Available?

Only huge names need apply for this list. Portland cannot afford to overpay for a not-quite star. They have a couple of those already. Mortgaging their future for another doesn’t make sense. Guarding against Fool’s Gold will be one of the main missions of the summer.

Two names have arisen prominently so far: Joel Embiid and Jaylen Brown.

Unless the Sixers flame out entirely—and Embiid starts punching teammates, fire extinguishers, and assorted small hamsters—I don’t see any way Philadelphia considers moving him. He’ll either be the reigning MVP or the next thing to it. They’d need to go into a total rebuild to make an Embiid trade make sense. And it’d take all of the capital listed above to snag him.

Brown is intriguing, but a couple of questions hover.

First, would he agree to extend with the Blazers? His current contract ends in 2024. Portland would be copying their pattern with Grant, looking to acquire him from a team he wouldn’t re-sign with, pledging to spend whatever it takes to keep him. That’s going to get expensive next summer.

Second, what is Boston looking to do? Everything in Portland’s package screams “new evolution”. The Celtics are trying to win a title right now and they’re not that far off. Wouldn’t they be more intrigued by veteran forwards the Raptors could offer than a package of guards and picks from Portland?

Speaking of the Raptors, Pascal Siakam definitely qualifies, but the Raptors are reportedly looking to move Anunoby instead. Whether he’d make enough of a difference—or anyone named Bridges, Towns, Plazas, or even Hamlets would—is up to debate.

Can It Be Done?

This is the thorny question. The fever that appears to have swept the franchise, fan base, and a portion of the media exists because of need, not probability. Those are two different things.

Nothing is impossible. Let’s get that right. It could happen.


If you were to describe, blindly, a 33-win team whose plan was to trade future assets for a franchise-transforming superstar in order to leap into contention in the next two years, the response would be, “Better be the Lakers.” Offering that the franchise was non-marquee, with no real track record of success and no huge draw, the response would change to, “Heh. Good luck.”

Appropriately so. If we’re going to opine that the Blazers could do this, why not the Washington Wizards? Or the Thunder? Or the Jazz? If trades like this were easy, why aren’t multiple teams succeeding this way?

We need to acknowledge that this “Big Trade” step is the question mark line in the old meme:

  1. Do X
  2. Do Y
  3. ?????
  4. Profit!

If the Blazers pull it off...YASSSSS! But if we acknowledge this as the central move of the summer—let alone the one all the others are built around—we also need to acknowledge that it’s probably on the same “dream” level as a Wembanyama lottery win. Maybe less so.

If the Big Trade doesn’t materialize, Portland is no better off than they started, give or take whomever they select with that lottery pick. It’s a get-rich-quick solution to issues that are usually solved over time, shrewdly, or at least with options and safety nets.

Every other decision point listed above involves multiple forks in the road ahead. The Big Trade doesn’t. It may not be all-or-nothing, but it’s definitely all-or-get-stuck, or failing that, having to re-frame the journey altogether. That should absolutely scare Blazers fans, especially with the low probability of actually getting it done.

What Didn’t We Ask?

You will note that we’ve left out two questions causing a fair amount of angst in Portland’s universe right now.

The first is whether the Blazers will retain Head Coach Chauncey Billups after two losing seasons. The team has given no indications of wanting to dismiss him. Until they send up a signal of some sort, we can’t regard it as part of their decision-making package this summer.

The second, and more pervasive, is whether Damian Lillard will demand a trade. As we explained in the above-mentioned podcast, this is completely beyond the franchise’s control. They’ve indicated that they want to keep him at all costs. They’ve already made their decision. The fate of the relationship now lies solely in his hands.

From a franchise—and fan—point of view, the only thing to say at this point is that Damian Lillard will do what Damian Lillard decides to do. It’ll be up to the Blazers to react appropriately either way.

Every bit of worry spent over someone else’s decision is energy diverted from the issues you’re called to manage. Portland will need to handle their own business well, then see what their superstar has to say as the results unfold. Nothing anybody does or says otherwise will change that.