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Trail Blazers Muted at Deadline, But Summer Offers More Trade Options

The Blazers are strategically setting up their pawns.

Minnesota Timberwolves v Detroit Pistons Photo by Brian Sevald/NBAE via Getty Images

The Portland Trail Blazers edged their way into two four-team deals at last week’s NBA trade deadline, neither of which moved the proverbial needle. In evaluating the transaction window, some could successfully argue that, on paper, the team got worse. While others might be right in suggesting the roster stayed the same or even got marginally better. But only the most cockeyed of optimists would be any more positive than that.

Suffice to say, if General Manager Joe Cronin’s goal was to build a contending team around Damian Lillard, there’s still a lot of work to do.

For those who haven’t been paying attention, the Blazers brought in Cam Reddish, Australia-American Mattise Thybulle, Ryan Arcdiacono and a protected 2023 New York Knicks first rounder for Josh Hart and a couple of seconds.

The team also received Kevin Knox II and five second rounders for Gary Payton II as part of a controversial deal involving the Golden State Warriors.

With Hart unlikely to pick up his $12.9 million player option for 2023-24, the Blazers got away from a player they were unlikely to re-sign while bringing in two young rotation pieces, a veteran backup point guard and a first rounder — a decent return. As for Payton II, if you want to believe the rumors about his discontent, then getting off his two years and remaining $18 million was probably a pretty shrewd move.

Both deals also generated trade exceptions for the Blazers, which may come in handy over the next 12 months with the payroll almost certainly set to remain above the salary cap.

Individually, Reddish and Thybulle probably won’t be as impactful as Hart, but together form two very playable guys on the wing. And while second rounds picks don’t do you any good on the court — can’t imagine Knox gets too much time — they aren’t terrible negotiation chips moving forward.

As far as contract statuses go, Knox hits unrestricted free agency in 2024 after being taken with the 9th pick in 2018. He earns $3 million this season and the same in 2023-24.

Both Reddish and Thybulle, taken as first round picks in 2019, hit restricted free agency in July. Reddish’s (10th pick) qualifying offer is set at $8.1 million while Thybulle’s (20th pick) is almost $6.2 million.

Portland will enter this summer with six players up for free agency, two unrestricted (Jerami Grant, Justise Winslow), two restricted (Reddish, Thybulle) and two veteran minimums in Drew Eubanks and Arcidiacono.

That leaves Damian Lillard, Anfernee Simons, Jusuf Nurkic, Shaedon Sharpe, Nassir Little, Kevin Knox, Keon Johnson, Trendon Watford and Jabari Walker as the remaining contracted players in 2023-24.

The Blazers also approach the summer with the potential for two first round picks, the lottery-protected Knicks selection and their own if they fail to escape the lottery.

But as I mentioned two weeks ago, the Blazers should be doing all they can to make the postseason and send that pick to the Chicago Bulls.

Even if it’s getting swept in the first round, the franchise can get some closure on that horrid Larry Nance Jr. deal executed by Neil Olshey in 2021.

Why? It means the Blazers finally convey their pick and Cronin can get on with doing what he has been talking about doing since he took the top job. He’s “anxious” to go all in.

“We’re borderline anxious to push all of our chips in. We cannot wait for that moment to happen, it just hasn’t come up yet. It’s my job to be the voice of reason, to be very diligent to not make a big mistake, to not get the wrong guy, to not overpay, to not give up on somebody that could eventually become a really good player. I’ve got to be really smart about this because it’s trying to thread a really thin needle here. We don’t have room for error, we need to get this right. We wanna maximize Damian’s time.

“I know it’s hard when I come out, like, ‘Oh, well, we’re looking forward to this summer,’ or ‘have faith we can get something done.’ It feels a little empty like it’s false hope or unrealistic promises, but hopefully our track record has shown that we’re willing to be really aggressive.”

“Certain things come into play whether it’s, we got a first and potential now five seconds. Those are good currency in the marketplace and definitely help enhance a package.”

“We’re definitely in position with a better asset pool than we started with and for me that’s really important.”

How do the Blazers get control of their first rounders this summer?

There are three ways this happens.

Option One. The Blazers make the playoffs and the pick conveys to the Chicago Bulls this summer. As simple as that and the most ideal option.

Option Two. The Blazers drop back into the lottery but offer the Bulls either the New York Knicks lottery protected pick or the five second rounders to get their 2023 pick back.

Option Three. The Blazers remove the protections on this year’s pick, regardless of where they finish, resulting in the pick certain to convey to Chicago.

I’d much rather the first two options, especially if the Blazers torpedo the rest of the season and come close to a mid lottery pick. If Option Two is in play they get to use their pick or incorporate it in a larger deal for a difference maker.

Thanks to the draft assets acquired at the deadline, Option Two becomes a real possibility and a real back-up plan if the Blazers miss the playoffs.

Once they have control of their first rounders

All types of options now open up for the Blazers to “push all their chips in”. Once the summer comes, Cronin is free to offer picks and pick swaps up until 2030. Assuming it’s Option Two, the Blazers will also have their 2023 pick, which gives them eight first rounders that can either be moved or swapped.

Eight picks combined with any combination of players that are not Damian Lillard and or are not entering any type of free agency.

As mentioned above, that’s Anfernee Simons, Jusuf Nurkic, Shaedon Sharpe, Nassir Little, Kevin Knox, Keon Johnson, Trendon Watford and Jabari Walker.

We have no idea which “push their chips in”-type player might be available come the summer. But I guarantee you, that at least one team will underperform through April and May, which may lead a star or two asking out of their current situation.

And so, with the Blazers regaining control of their draft destiny, an attractive trade package can be put together that would, at the very least, prompt a trade partner to consider.

I really don’t like suggesting trades but I’m also a glutton for punishment, so here goes.

If I’m Cronin, I’m looking at Pascal Siakam (Toronto Raptors), Karl-Anthony Towns (Minnesota Timberwolves), maybe Jimmy Butler or Bam Adebayo if the Miami Heat flame out, Wendell Carter Jr (Orlando Magic) and Mikal Bridges, now of the Brooklyn Nets.

You might make a play for Jaylen Brown of the Boston Celtics, perhaps the Los Angeles Lakers’ Anthony Davis or Los Angeles Clippers’ Paul George. I might also be dreaming but perhaps Joel Embiid if the Philadelphia 76ers fall flat in their face over the next few months.

I’m finally at the point where I’m allowing myself to think big.


I know a lot of people weren’t happy with the moves made at the deadline. But the draft compensation acquired removes one of the main roadblocks to this team making a big move to bring another star in alongside Damian Lillard.

This front office is well and truly changed since Olshey. They’re not giving up first round picks for the likes of Larry Nance Jr. or multiples for Robert Covington. Dare I say, and this is just my opinion, but I wouldn’t have been shocked if Olshey had found a way to give up a first for Jarred Vanderbilt at the deadline.

Cronin is going to make a bold move, but it’s a move that makes a real change and real sense next to Lillard. Think about the fact that through the CJ McCollum deal with the New Orleans Pelicans last year, Cronin was able to secure Jerami Grant with a trade exception and a distant Milwaukee Bucks first rounder. This instantly won my trust and patience.

We know Lillard is 32 but he and Cronin appear to be on the same page and he is clearly prepared to give him time to make that deal. But we can’t wait forever, a deal needs to happen this summer — so if this team is essentially unchanged by the end of August, I might start dusting off my pitchfork.