NBA Offseason Guide 2022: How the Portland Trail Blazers can bounce back next season

If the second half of the season is an indication, expect a long rebuild in Portland.

Following the All-Star break, the Trail Blazers lost 14 games by at least 30 points, the most 30-point losses in a season in NBA history.

That type of losing doesn't sit well with Damian Lillard.

"A tough season, a lot of adversity this year. A lot of things came up that we didn't expect," Lillard told fans before the season finale. "But I want you to know one thing: This will not continue. Next year, we're gonna be back better than before."

Fortunately, the Trail Blazers have the resources with draft picks, trade exceptions and potential cap flexibility to make sure that the losing in Portland won't continue.

State of the roster

Roster status: Expedited rebuild

The Trail Blazers waved the white flag at the trade deadline, stripping down the roster and using the last 30 games as an audition for next season.

The challenge now comes with expediting a rebuild that is only two months old around the timeline of franchise guard Lillard.

"I still feel uncomfortable about it," interim general manager Joe Cronin said after the season. "We have a really competitive group. We didn't want to lose ballgames. Sometimes it's necessary. Sometimes you have to go with your youth movement ... this, theoretically, is a really quick step backward. We're not looking at two, three, four years of this. But as far as the discomfort, the willingness to accept losing, that was really hard for us and continues to be."

Cronin has torn down the roster since Neil Olshey's departure in December, and now ownership has a decision to make on whether to lift the interim tag and name Cronin the permanent head of basketball operations or go in a different direction.

Why the Trail Blazers do not have time on their side is because of Lillard.

He has three years left on his contract, and players of his ilk often would ask out when the word rebuild is mentioned. But Lillard, at least for now, has bought into the roster strategy of the Trail Blazers.

"We've positioned ourselves to do something that we haven't been able to do since I've been here, which is we've opened up money, we got picks, we got a $22 million trade exception, we got a $6 million trade exception, we got the full midlevel, we got the biannual," Lillard told Yahoo's Chris Haynes. "We have an opportunity, and we got flexibility. There are guys we can bring in that can make us a team that can compete for a championship, but we have to execute that."

The executing part, of course, is the most difficult part; and if the Trail Blazers stumble this offseason, it could take years before they are contending for even a play-in spot in the Western Conference.

The accelerated rebuild

Lillard is right that the Trail Blazers have the resources for a quick turnaround.

They have a lottery pick that they can package for an established player or keep and develop. A second lottery pick was lost when the New Orleans Pelicans earned a spot in the playoffs. Portland will now have a top-four protected 2025 first-rounder from the Milwaukee Bucks.

How the Trail Blazers add players around Lillard is dependent on whether they want to act as a team with room or operate over the salary cap. Creating cap space would come at an expensive price.

Not only would the Trail Blazers have to renounce their $20.9 million trade exception. They also would have to renounce all their free agents (including Jusuf Nurkic) except for Anfernee Simons and also waive Eric Bledsoe and Josh Hart. Bledsoe has $3.9 million in protection, and Hart's salary does not become guaranteed until June 25.

" is the type of player that we definitely want to build around," Cronin said of the center, who will be an unrestricted free agent.

The decision to waive Hart is a nonstarter because of the value he brings on the court (19.9 points in 13 games with the Trail Blazers), his locker room leadership and the team-friendly contract he is on.

In the scenario that Portland does create room, it would enter free agency with $35 million of space but a roster that except for Lillard resembles one of an expansion team. If Hart is on the roster, cap space would shrink to $23 million.

"As free agency goes, we're confident that we can go out and be competitive in our recruiting," Cronin said. "I think with Chauncey Billups, me and Lillard, I think that we will get in meetings and we will paint a very good picture of this organization and this city. And we're not going to run from players that we think make sense here."

Outside of Bradley Beal, Zach LaVine, Kyrie Irving, Jalen Brunson and restricted free agents Miles Bridges and Deandre Ayton, the 2022 free-agent class is below average. The likelihood is that each of the marquee free agents mentioned will remain with his current team.

The more likely and logical scenario is Portland staying over the cap and focusing on its own free agents (Simons and Nurkic), exploring trades with the $20.9 million exception (it also has a $6.5 million exception and a $3.3 million exception) and using its $10.3 million midlevel exception in free agency.

There is less risk involved by staying over the cap, and it gives Portland more options on how the roster is built.

"To win in this league, you got to have really good players," Cronin said. "We have the style of play we want to achieve and this mentality that's really important to us, but at the same time, we need these players to be high-end talent. We also want this roster to be sustainable, that it's not a two-year wonder; we want this roster to grow and be continually competitive."

Damian Lillard

Lillard is adamant that his future is in a Portland uniform and that he wants to be part of the solution.

"I sit in the office with Chauncey every day, and we trying to find solutions, and I'm dealing with these people every day that walk in our practice facility trying to find solutions," Lillard said. "So why would I be a part of trying to find solutions if I'm planning on an exit? That's not what's going on; but people want that so bad, and it's a good story and good things to talk about, and they know people gonna entertain it, so they continue with it. But my intentions are to be in Portland and to figure it out. As far as I know, that's all of our intentions."

Lillard is entering year two of the supermax extension he signed in 2019, and although he has three years left (there is a player option in the last year), he is eligible in July to tack on two additional years.

SEASON SALARY AGE

2025-26 $51.2M 35

2026-27 $55.4M 36

It is nearly impossible to predict the future, but that is exactly what the Trail Blazers' front office needs to do when weighing a $107 million extension for a player turning 35 in the first season.

Do the Blazers reward Lillard for the unwavering support and loyalty shown to the organization? Or do they table discussions until after the 2022-23 season?

Prior to this season, Lillard had been one of the more durable players, missing only 55 games since 2012. The abdominal injury and eventual surgery in January cost him the remainder of the season. While nobody wants to sit on the sideline rehabbing, the injury to Lillard could prolong his career.

"It's the first time that I can say I am pain-free since maybe 2016, 2017," Lillard told Yahoo Sports. "I haven't had a chance in 10 years to take a step back and let my mind relax and to let my body fully recover and relax and have a true opportunity to ramp up and train and start back with my foundation, who I am as a player and spend time with my family, my kids and my wife. So, I feel strong, mentally and physically."

Anfernee Simons and Nassir Little

Simons and Little are at the forefront of the Trail Blazers' rebuild.

Because there are roadblocks of adding in free agency and with trades, the development of both former first-round picks will play a big role in how quick this roster improves.

Simons is a restricted free agent, and the Trail Blazers have made it known how important he is to their future.

"A core piece, definitely," Cronin told the Washington Post's Ben Golliver. "We wanted to create a runway here for him."

The runway Cronin mentioned are the trades of CJ McCollum and Norman Powell at the deadline along with playing more of a feature role because of the injury to Lillard.

After Jan. 1, Simons was one of four players (Kevin Durant, Tyler Herro and Kyrie Irving) to average at least 20 points and 40% on 3-pointers, according to ESPN Stats & Information research. Simons also attempted 10.4 3-point attempts per game (converting 42%), second most in the NBA behind Fred VanVleet. In 2021-22, Simons shot 46.6% on catch-and-shoot 3s, the highest rate in the NBA among players with 200 attempts. This season, Simons had the biggest increase in points per game (plus-9.5) from the prior campaign.

The concern moving forward is not if a Lillard and Simons combination can work on offense but the liability on defense. Per Cleaning the Glass, the Trail Blazers gave up 119.3 and 124.3 points per 100 possessions the past two seasons when both players were on the court.

Those numbers should improve as the roster continues to evolve and in a second season under Billups.

As for a new contract, the five-year, $90 million deal that Powell signed in August is a comparable salary. An average of $16 million per year appears as an overpay especially when you consider Simons started only five games before this season.

However, when you consider that Simons will be only 23 years old when next season commences, the development he showed this season and teams like the Detroit Pistons and Orlando Magic that have significant cap space to make an offer sheet, Portland will need to take an aggressive approach.

Little is not a restricted free agent, but because he is entering the fourth year of his rookie scale contract, there isn't a sense of urgency to complete a new deal at the start of free agency.

While a priority, Portland can slow play negotiations, see how the free-agent market develops and formulate a plan as the mid-October deadline approaches.

Little started a career-high 23 games, averaging 11 points and 5.8 rebounds.

In the 690 possessions that Simons and Little played together this season, Portland was a plus-10.7 in points per 100 possessions, according to Cleaning the Glass.

Offseason cap breakdown

Portland Trail Blazers 2022-23 Salary Breakdown

PLAYER CAP CHANGE

1. Damian Lillard $42,492,492

2. Nassir Little $4,171,548

3. Justise Winslow $4,097,561

4. Keon Johnson $2,681,040

5. Didi Louzada $1,876,222

6. Greg Brown $1,563,518

7. Trendon Watford $1,563,518

8. Eric Bledsoe $19,375,000 (partial guarantee)

9. Josh Hart $12,960,000 (non-guaranteed)

10. Jusuf Nurkic $19,875,000 (free agent hold)

11. Joe Ingles $16,295,456 (free agent hold)

12. Anfernee Simons $11,816,454 (free agent hold)

13. Elijah Hughes $2,011,516 (free agent hold)

14. CJ Elleby $2,011,516 (free agent hold)

15. Ben McLemore $1,811,516 (free agent hold)

16. Keljin Blevins $1,616,044 (free agent hold)

17. First-rounder (own) $6,498,600 (draft hold)

-- Andrew Nicholson $2,844,429 (dead cap hit)

Guaranteed salary $68.8M

Dead money $2.8M

Non-guaranteed $28.4M

Free-agent hold $55.4M

Total salaries on cap $155.6M

2022-23 NBA SALARY CAP $122M

2022-23 NBA LUXURY TAX LINE $147M

Portland Trail Blazers Depth Chart

PG SG SF PF C

D. Lillard J. Hart NG N. Little J. Winslow

E. Bledsoe PG D. Louzada NG K. Johnson T. Watford

G. Brown

PG=Partially guaranteed

NG=Non-guaranteed

Team needs

• Starting power forward and center

• Bench depth

Resources to build the roster

• The draft: 3 picks, including one in the lottery

• Own free agents: Anfernee Simons and Jusuf Nurkic

• Cap flexibility: The possibility to create up to $35 million

• $20.9 million trade exception if room is not used

• Exceptions: $10.3 million midlevel and $4.1 million biannual

• Cash: $6.3 million to send or receive in a trade

Dates to watch

June 25: Don't expect to see Hart on the waiver wire. Hart has a $12 million non-guaranteed contract, and although the Trail Blazers can create room by shedding his salary, his value on the court outweighs cap flexibility.

June 29: The Trail Blazers will tender Simons a $5.8 million qualifying offer by the end of June. Simons had a career season but failed to reach starter criteria (41 starts or 2,000 minutes). If he had met the criteria, the qualifying offer would have been $7.9 million. They also have a decision on whether to tender Elijah Hughes ($2 million), CJ Elleby ($2 million) and Keljin Blevins ($1.8 million) a qualifying offer.

July 10: The decision on Bledsoe's $19.4 million partially guaranteed contract will be based on whether the Trail Blazers see the guard as a trade asset on an expiring contract or a dead cap hit that is taking up a roster spot. Bledsoe has $3.9 million in guaranteed salary, with the balance becoming fully protected if he is not waived by July 10. Bledsoe has been dealing with tendinopathy in his left Achilles tendon and did not play in a game for Portland since he was acquired in early February.

Restrictions

The salary that is guaranteed in the Hart contract (zero) and Bledsoe contract ($3.9 million) for next season counts as salary in a trade.

Portland owes the Chicago Bulls a lottery-protected first-round pick from 2023 to 2027 and is restricted from trading any of its own firsts in a deal. The Trail Blazers can trade their 2022 first on draft night. They also are allowed to trade the 2022 first they received from the Pelicans.

Extension eligible

Besides Lillard and Little, Bledsoe is the only player on the roster who is extension eligible. It is unlikely that Bledsoe is on the roster at the start of training camp.

The draft

The Trail Blazers' first-round pick in June was sent to Chicago as part of the Larry Nance Jr. trade. However, because the Blazers are in the lottery, they will retain it this season.

The first is top-14 protected over the next six years. From the McCollum trade, Portland has a top-four protected first from Milwaukee in 2025.

Here's how ESPN's Jonathan Givony and Mike Schmitz have Portland selecting in June:

No. 6 (own): Shaedon Sharpe, Kentucky, SG

Sharpe's best NBA-ready skill is his shooting. He sports compact mechanics that start with excellent shot preparation. The ball comes out of his hands cleanly, and he doesn't need to be perfectly on balance or set to knock down shots, which is a big part of what gives him so much upside as a scorer. He doesn't always need a ball dip to generate rhythm off the catch. He showed the ability to make shots off the dribble, as well, even if he looks better on pull-up 3s than midrangers at this stage. -- Schmitz

No. 36 (own): Christian Koloko, Arizona, C

Koloko's 7-foot-4 wingspan, outstanding mobility and quickness getting off his feet make him a force both around the rim and in covering ground on the perimeter, where the Pac-12 defensive player of the year and most improved player often is asked to guard smaller players in Arizona's jumbo lineups. He is an excellent finisher and a much-improved offensive player, in general. Koloko's thin frame, lack of physicality and developing feel for the game -- which manifests itself in foul trouble, point-blank misses and struggles keeping up with the speed of the game -- are things NBA scouts will want to learn more about in high-stakes matchups with pro-sized frontcourts as the competition stiffens. -- Givony

No. 57 (via MEM): Alondes Williams, Wake Forest, PG/SG