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What If the Trail Blazers Don’t Get It Done this Offseason?

It’s worst case scenario time.

Golden State Warriors v Portland Trail Blazers - Game Four Photo by Jonathan Ferrey/Getty Images

As we know, the Portland Trail Blazers have a big summer ahead of them. The franchise’s short- and long-term future could very well be decided by the annual rigmarole of trade season, the NBA Draft and free agency.

What makes this particular offseason so poignant is urgency. And by urgency, I mean contemplating a reality where Damian Lillard doesn’t play his career out at the Moda Center.

It’s been discussed for years but it seems Blazers General Manager Joe Cronin has three months to swing a significant trade or the door opens to the potential end of Lillard’s time in Portland. This is no mean feat, considering how the roster finished the 2022-23 season and the assets Cronin has managed to build from virtually nothing over the past two years.

Of course we’re all hoping he gets it done, but by his own admission, Cronin is a relative neophyte in his role and nothing is guaranteed when it comes to team building in the NBA. Just ask New York Knicks fans who thought they were getting Kevin Durant and Kyrie Irving in 2019 — maybe not the best example four years on.

A front office might have the best of intentions, but if it’s unable to execute then there’s nothing to celebrate. And because of this, plans B-through-Z need to be firmly established.

The case isn’t hopeless. Cronin methodically executed under-the-radar deals at the 2022 trade deadline, setting up the Jerami Grant trade four months later. The new regime has done a decent job, cutting fat, bringing in picks, young talent and salary-appropriate players over the past 17 months. Cronin has also publicly vocalized eagerness — reinforced at his exit interview — to take a swing, something his predecessor avoided like the plague.

Also re-assuring is that the General Manager seems to be in step with his star player. During Lillard’s-own exit interview he highlighted a confidence he had in his front office, despite emphasizing the widely-felt impatience for more mediocrity.

It’s clear that with Lillard’s 33rd birthday approaching, there’s no more time to beat around the bush. No more 19-year-olds, it's time for veterans and contention. Lillard is done watching other franchises play deep into May and June.

The franchise is going to try to keep it’s arguably greatest player happy. But if it all falls through, this franchise and fanbase might need to get used to another couple of losing seasons.

It’s easy to hope for the home run swing. But what does it look like if the Blazers can’t follow through? What might Steps B-Z entail. It won’t be pretty, but let’s look.

What does not getting it done mean?

With free agency an unrealistic avenue given the Blazers’ current cap situation, trade is their only path to basketball nirvana. In order to get a huge deal done, the Blazers are going to have to part with this year’s lottery pick and possibly others, which means re-negotiating current obligations to the Chicago Bulls.

Combining picks with an asset like Anfernee Simons is likely the only way Cronin even comes close to big names like Jaylen Brown, Pascal Siakam, Mikal Bridges, or Jimmy Butler.

There is, of course, one caveat. If the Blazers land the number one pick in the 2023 NBA Draft, they make an initial call to the Milwaukee Bucks for Giannis Antetokounmpo. If that fails, they should remain supremely confident about Victor Wembanyama’s impact on the NBA over the next decade or so.

If there’s no number one pick and the trade isn’t done, then the Blazers probably need to rebuild, again. And ideally it happens sooner than later.

Ultimately, it’ll be up to Lillard if he wants to move on. But from what we’ve heard, he’s probably not prepared to go through another average-to-disappointing season.

So, not getting it done means the Blazers don’t get the first overall pick and are unable to execute a trade that brings in a difference-maker. It’s as simple as that. Maintaining the existing roster with minor upgrades here and there — also known as the Olshey Way — does not work.

What happens then?

First and foremost, if it’s time, the Blazers and Damian Lillard move on amicably, sending the seven-time All Star to a preferred destination while getting the franchise an optimal return.

As far as timing goes, the Blazers can probably move Lillard at any point during the offseason and still yield a haul of picks, legitimate young talent, and/or contract-friendly players. There are no time pressures here.

However, in order to set the team up and bounce back as well and as quickly as possible, it’d be better for a decision to be made earlier than later.

Why? Because of Jerami Grant. If a decision on Lillard’s future is made before the free agency clock starts on June 30, the Blazers may be able to work 29-year-old unrestricted free agent into a sign and trade, a deal that brings real pieces back to Oregon.

The free agency moratorium runs between July 1 and 6, after which players can start signing deals. If the Blazers pen Grant to a new contract before making a call on Lillard, they won’t be able to trade him until midway through the 2023-24 season.

A Grant sign-and-trade gets the rangy wing to a situation of his choosing, a team that probably hasn’t got the cap space to sign him outright, while bringing the Blazers a collection of players and picks.

Jusuf Nurkic would also need to be dealt for the best deal possible. Expectations aren’t high but if they received anything of value, it’s a win.

What would the team look like on opening night?

Assuming this dreary future becomes reality, I’d prefer nobody on the roster older than 27. Sure, Cronin said he wants more veteran-laden talent, but re-booting without Lillard changes things.

Salary will obviously have to come back for Lillard, Grant and Nurkic, but as long as the Blazers don’t gum it up with other expensive veterans, the books will likely be considerably cleaner down the road with picks aplenty.

Anfernee Simons and Shaedon Sharpe would become the beneficiaries and move forward as the franchise’s future backcourt, a promising one at that. They might be able to snag Brandon Miller with that lottery pick, becoming the third name in a trio that could eventually lead the Blazers back to the top of the tree.

You’d imagine Matisse Thybulle and Cam Reddish come back, surrounded by Nassir Little, Trendon Watford and the prospects yielded in Lillard and Grant trades.

This gang of young players gets more time to make mistakes and develop, sinking the Blazers back into the lottery.


Cronin can’t wait until late July and August to swing a franchise-changing deal. The sooner it’s done, the more options he’ll have in building a contender around Lillard.

The odds of him getting a deal done aren’t great though. A lot has to go the Blazers’ way. if It doesn’t happen, Cronin may have to turn to Simons, Sharpe, and the yet-to-be-named lottery pick to take the franchise into the future.

I want to be abundantly clear, I am in no way wanting this to happen — it’s a worst-case scenario. How bad would it be? That would be determined by the players who are staying, plus the quality of the haul Cronin got in exchange for his veterans.

How about you? How disappointed would you be if Portland had to start the season with Simons, Sharpe, a lottery pick, plus hopes and dreams for the future?