Trail Blazers end disastrous season with big offseason plans — again: ‘We have to be aggressive’

The Portland Trail Blazers began the 2022-23 season with a victory at Sacramento in October that sparked a 10-4 start.

On Sunday, the Blazers ended the season by losing their 15th game in 17 outings, fueled by the franchise’s desire to better its chances of winning the NBA draft lottery.

Sound familiar?

It should because this is also how last season ended.

What also should sound familiar were the declarations made by general manager Joe Cronin, coach Chauncey Billups and superstar Damian Lillard that the franchise can make major moves this offseason to not only turn the franchise around, but make it a contender.

Of course, that would require Cronin pulling off what would be the greatest trade in franchise history.

Confidence or delusion? Tough to say.

The only real difference between this offseason and those of the past is that maybe, just maybe, the Blazers have enough assets to finally make a splash in the trade market that could change the fortunes of the franchise before Lillard’s superpowers begin to fade.

Lillard, 32, said after Sunday’s season-finale loss to Golden State that he feels good about the upcoming offseason and definitely sees a road toward bringing in the talent needed to contend. However, he has felt that way in the past when even the best-laid plans ultimately fell flat.

“I’m always optimistic,” Lillard said. “I’ve been in the league long enough to know that things don’t always work out the way you want to see it all work out. There’s a lot of moving pieces. So, I feel like over the last few years I go into it with these high expectations that it’s going to be different. Obviously, I feel how I feel about Chauncey. I feel how I feel about Joe. And I feel how I feel about myself. I think that the optimism is there. I feel optimistic about it. But I think it’s just time to just get the work done for all of us.”

The “work” Lillard referred to is not merely about adding minor pieces, although that will also be within the framework of the offseason. The Blazers need an All-Star-caliber player to give Lillard a chance to bring a championship to Portland.

“I think we’ve done the tweak thing a few times,” Billups said. “I think we’ve got to be more aggressive than that. That’s just my opinion. If we want to actually do right by the best player in the history of this organization, we have to be aggressive.”

So, why could this offseason be different?

The Blazers are loaded with arguably more attractive assets to pull off a major deal than they’ve ever had, save for when they landed the No. 1 pick in 2007.

By finishing with the fifth-worst record in the NBA at 33-49, the Blazers will have a 10.5% chance of winning the NBA draft lottery on May 16. Receiving the No. 1 pick would likely lead to the Blazers drafting Victor Wembanyama, a 19-year-old, 7-foot-5 center out of France, who is viewed as a potential instant franchise-changer along the lines of LeBron James when he entered the NBA in 2003.

Falling into any other draft slot, however, likely would lead to that pick being dangled in trade talks.

The Blazers will have their lottery pick as well as the New York Knicks’ first-round pick (likely No. 23). Plus, the development of rookie Shaedon Sharpe, 19, and guard Anfernee Simons, 23, could make them attractive in a deal with a team seeking to go young and rebuild.

The key questions then would be, what team could seek to unload a star and what would their asking price be? Also, how would the Blazers value that desired player against their lottery pick.

“The goal is to get better as soon as possible,” Cronin said. “The pick itself, we’ll see where it lands. We’ll see what its value is. You have to go through that whole process, kind of like we did last year with the pick. But, timeline-wise, it’s time for us to start moving quicker towards having a roster that’s ready to compete at the highest level. So, if that means using that pick or other picks in deals, where it’s getting aggressive to go get stuff done, yeah, we’re open minded to that.”

Lillard certainly is. When asked if he would want to see the team land another young player like Sharpe, taken with the No. 7 pick in last year’s draft, Lillard made it clear that the Blazers need veteran, proven winning players now.

“I don’t have much of an appetite for bringing in guys two and three years away from really going after it,” Lillard said. “I think we get Shaedon at 19 and he’s just different. Just being around him, his disposition, how he listens, his frame, his natural talent and his ability. I think, that’s enough 19-year-olds. You probably won’t find one that will come along the way he has. I’m just not interested in that.

“And this is not a secret. I want a chance to go for it. And if the route is to do that, then that’s not my route. I think we’re all in line with doing what we got to do to put a team together that we can actually go out there and get something done.”

One of the main issues for the Blazers during past pursuits of star players has been finding one who wants to be in Portland. Last offseason, it was a virtual lock that the Blazers would trade for Jerami Grant. He and Lillard were pals. Detroit wanted to trade Grant and didn’t want to take on salary. The Blazers had a $21 million trade exception and a 2025 first-round pick to offer. Boom! Done deal.

But are there players a level up from Grant who could be had?

Yes, according to Lillard.

“I know there’s guys that really move the needle that want to do it,” Lillard said. “But knowing that and then actually making something happen to make that a reality is a completely separate thing.”

Cronin agreed.

“We have our target group,” he said. “The guys that we really like, that we think would be terrific fits here. Many of them, we pursued last trade deadline but just weren’t able to get anything done. But, obviously, we’ll circle back on that group and hopefully add to it. You want that list as broad as possible.”

What Cronin wants to avoid is making a mistake with the lottery pick. Last season, trades were on the table for the No. 7 pick and Cronin said he is glad he rejected those and instead selected Sharpe.

Consequently, any player targeted in a trade involving the Blazers’ 2023 lottery pick must be a can’t-miss piece who makes giving up a potential young star easier to stomach.

“If we’re committed to winning now, we have to be able to live with what the future holds for some player that we’ve traded,” Cronin said.

Whether the Blazers land a star or not, an area of need that cannot be ignored is adding more veteran talent.

When injuries hit the roster this season, the Blazers found themselves turning young and/or relatively inexperienced players such as Sharpe, Trendon Watford, 22, Nassir Little, 23, Jabari Walker, 20, Drew Eubanks, 26, and Keon Johnson, 20.

“All of the sudden, we’re starting to count on players that weren’t ready to help us yet,” Cronin said.

That reality often left Billups in bad situations, trying to piece together functional lineups.

“I think we all, if we’re watching this game close enough, and we understand what teams in this league, as the playoffs start, and these teams start to get eliminated, you get to the final four, you’re not gonna see teams with four and five, six and seven young guys,” Billups said. “It just doesn’t happen.”

Last offseason, Cronin said he knew that he left Billups with more talent after the acquisition of Grant and seeing Sharpe develop. But Cronin said he also knew that there wasn’t enough balanced depth on the roster to overcome injuries.

“I think if we can get out of this offseason with some key additions at some key positions throughout our rotation, and if we can walk out of, say, we leave August and we’re full, or we feel like we have nine, 10 guys that can really play,” Cronin said, “I think we’re doing a pretty good job.”

Pretty good would make the Blazers better. But the goal is become very good, and that is going to require something major to happen.

— Aaron Fentress | afentress@Oregonian.com | @AaronJFentress (Twitter), @AaronJFentress (Instagram), @AaronFentress (Facebook). Subscribe to Oregonian/OregonLive newsletters and podcasts