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Which Trail Blazers Free Agents Will Come Back Next Season?

Six Blazers head into free agency in July, but who returns?

NBA: Oklahoma City Thunder at Portland Trail Blazers Soobum Im-USA TODAY Sports

There are no doubt thousands of Portland Trail Blazers fans sick of stories talking up possibilities for General Manger Joe Cronin to execute this summer.

But sorry, here’s another one.

Though it might be a bit early to speculate on NBA free agency, there are still six Blazers up for grabs in July — two unrestricted, two restricted and two veteran minimums.

The obvious concern for the front office is Jerami Grant. The high-level two-way forward has reportedly already turned down an extension to stay with the Blazers after joining the team in a trade with the Detroit Pistons last June.

While it might look like panic stations, the inside word is that Grant has no interest in leaving, he just wants a more lucrative, longer-term deal with the Blazers.

No issue with this, he’s earned it.

Other Blazers set to hit the market include Justise Winslow, restricted free agents Cam Reddish and Matisse Thybulle and vet minimum guys Drew Eubanks and Ryan Arcidiacono.

While obviously lower on the priority list, the quintet’s next contracts will have an impact on where this roster goes down the line.

As we heard from Cronin last week, the team is “borderline anxious” to push its chips and give Damian Lillard enough time to legitimately contend. So we may see some of the boldest trades this franchise has done in more than a decade this summer. Fingers crossed.

Having said all that, if any of these guys are brought back, they’re likely on this team come opening night in October, given the complexities surrounding sign and trades.

Jerami Grant

As mentioned, Grant is a must re-sign, despite already turning down a four-year, $112 million extension. If he does leave — the only likely team that could have cap space is the Los Angeles Lakers — the Blazers would be left with limited avenues to improvement.

The soon-to-be 29-year-old has exceeded all expectations since his arrival, offering above-average one-through-five defense while hitting more than 40 percent of his threes on more than five attempts a game.

If he does secure an annual $30 million salary, he’ll be worth it. And if there is a deal already on the table at the stroke of free agency, the Blazers should have no regrets executing it.

Aside from swinging a franchise-changing trade to support Damian Lillard, Cronin’s priority come July 1 should be Grant’s return.

This season: 54 games, 20.8 points, 40% 3pt, 4.3 boards, 2.3 assists, 0.8 steals, 0.8 blocks

New deal: Four years, $122 million

Verdict: Stays

Justise Winslow

For regular readers, you know how much I appreciate what Winslow brings to this team. But with the Blazer’s only holding Winslow’s Early Bird Rights, they’re limited to what they can offer.

I’m not sure he gets big money, but I also think there will be multiple suitors willing to pony up more than $4 million he's currently taking home. Whether the Blazers are prepared to match such an offer remains to be seen but despite his lack of shooting, Winslow offers a plethora of skills that contribute to winning. There’s every chance he returns but I wouldn’t be shocked to see him sign elsewhere if his price is too much for the Blazers to meet.

Also important to note, that if the Blazers bring back its two restricted free agents (listed below), the roster will already be well endowed with — not necessarily starting — but rotational wing talent on both sides of the floor.

This season: 29 games, 6.8 points, 31% 3pt, 5.0 boards, 3.4 assists, 1.0 steals, 0.4 blocks

New deal: Two years, $12 million

Verdict: Gone

Cam Reddish

One of two restricted free agents brought in at the deadline, Reddish is a reclamation project. And while this team doesn’t have time for players to find themselves, Reddish sill has the ability to contribute in the short term.

Restricted free agents rarely fly the coop and my gut tells me Cronin sees Reddish as more than just salary filler in the deadline deal with the New York Knicks.

If Reddish meets the potential that saw him selected 10th in 2019, then he’s the prototypical small forward, big, long, athletic and able to compete on both sides of the ball. Best case scenario, he’s a carbon copy of Grant, offering a serious two-way option at the starting forward positions.

You’re not giving up on him after two months.

This season: 24 games, 9.4 points, 32% 3pt, 1.7 boards, 1.2 assists, 0.8 steals, 0.4 blocks

Qualifying Offer: $8.1 million

New deal: Three years, $21 million

Verdict: Stays

Matisse Thybulle

I’m probably a little biased given his national team representation, but Thybulle performs a sought-after NBA skill at an absolutely elite level, it just a shame he’s not able to contribute on the offensive end.

Sure, he hit four threes in his Blazers debut, but until Thybulle is able to deliver on that end consistently, he’s limited.

On defense, limiting is what he does — arguably the best wing defender in the league, well according to Cleaning The Glass, he’s in the 99th percentile in both steals and blocks.

Like Reddish, he was probably more than just filler in the Hart deal and, as such, you’re not parting with him after such a short stint.

This season: 52 games, 2.9 points, 35% 3pt, 1.4 boards, 0.5 assists, 1.0 steals, 0.3 blocks

Qualifying Offer: $6.2 million

New deal: Four years, $20 million

Verdict: Stays

Drew Eubanks

The hometown hero stays. Not much to say here. He’s a third string center that started the last seven games before the All Star break, primarily due to the lack of size on the roster.

If he was a couple of inches taller, he’d be a regular rotation piece on a contending team. Regardless, he deserves a spot in the NBA thanks to his athleticism and energy. Absolutely no issue with him sitting at the end of the Blazers bench next season.

This season: 56 games, 6.0 points, 5.0 boards, 1.2 assists, 0.5 steals, 1.2 blocks

New deal: veteran minimum

Verdict: Stays

Ryan Arcidiacono

Arriving in Portland as a likely thrown-in in the Josh Hart deal, there’s every chance Arcidiacono is kept but average third-string point guards can easily be had on veteran minimum contracts. Unlike Eubanks, Arcidiacono has spent only two weeks in Portland. He should find another place in this league but he shouldn’t be a high priority for the Blazers.

This season: 14 games, 0.9 points, 0.7 boards, 0.6 assists, 0.1 steals,

New deal: veteran minimum

Verdict: Gone


That’s four out of six returning. But I wouldn’t be shocked to see Cronin bring all six back. If we’re believing the vibe coming out of the front office, the Blazers will be eager to execute a franchise-changing trade this summer, potentially bringing back less players than they send out.

If that’s the case, they’re going to want to secure rotation-level players to fill out the roster with Lillard, Grant and whoever they bring in. Yes, I realize I didn’t mention Anfernee Simons, but perhaps he’s used as a contract in said big deal.

Grant is a must return and is worthy of the money suggested. Reddish and Thybulle are decent enough rotation restricted free agents that can be had on relatively decent deals. There is a deal of sentimentality surrounding Drew Eubanks who’s perfectly fine rounding out the 13th, 14th or 15th roster spots.

This summer is set to be one of the more interesting in recent Blazers memory. All of the above could be completely wrong, but at this point in time, the four players mentioned seem more likely to return than not.