Trailblazers must rely on Justise Winslow in Free Agency

I’m not a fan of people saying “I told you so”. But, I mean, I told you all that Justise Winslow would play an important role in that Portland Trail Blazer Franchise.

I said it in February, August and October.

Right, Schadenfreude out of the way.

Now the Blazers have a decision to make. And they have until the close of trading to make it.

The decision to either try to re-sign Winslow in July or trade him up to ensure they don’t lose him for nothing after February 9th.

The 26-year-old was part of the controversial trade in February Los Angeles Clippers, along with Eric Bledsoe, Keon Johnson and a second-round pick for Norman Powell and Robert Covington. This deal is looking better for the Blazers every day.

And while his arrival met with little to no expectation for some, the 6’6 forward has proven to be an incredibly handy NBA player for some national pundits of late Compare him to Golden State Warriors mainstay Draymond Green.

And for a good reason. Winslow’s team-first focus and ability to competently defend positions one through five have made him a revelation from the Blazers bench. Yes, he probably doesn’t score enough goals to enter the sixth man of the year debate, but he’s everything this franchise needs from a larger, athletic, and skilled reserve.

Sure he can’t shoot. But this team has a lot of shooters. However, defense, ball handling, passing and basketball IQ have been invaluable since his arrival and are even more important this season as the Blazers sit at the top of the Western Conference.

Like Draymond Green, the man does intelligent things on the floor. It’s innate, whether it’s a pass, a parry and save, or a slash, it’s an ability to be in the right place at the right time.

There was a reason the former duke was supposedly worth it four first-round picks by the Boston Celtics to Danny Ainge on draft night 2015. Yes, injuries, reduced opportunities and periods of poor form have held him back, but natural ability will always find a way to prevail.

Statistically, his season numbers — 7.9 points, 31 percent from three, 5.1 boards, 3.5 assists and 1.3 steals — despite a nearly triple-double against the Phoenix Suns on Nov. 4, don’t do justice to his contribution. Do you see what I did there?

But Winslow isn’t necessarily needed to come up with gaudy numbers. His value lies behind stats by doing all the little things that make his teammates and the team better.

If the Blazers are looking to keep Winslow beyond the 2022-23 season, there are a few factors at play. Given the nature of his $4.1 million contract, particularly his early bird rights, the franchise doesn’t have the same options as other contract players. We discuss this below.

Other moving parts

As mentioned countless times before, Josh Hart seems to be the Blazers’ best trading chip. He’s capable at both ends of the floor, and with his $12.9 million deal this season and a likely unclaimed $12.9 million player option next season, Hart almost certainly has to be on the be block.

Cronin has said openly that he still has it work to improve this team and given the franchise’s payroll, it seems commerce, internal growth, and smart, deep decisions are the only way forward.

While Winslow didn’t contribute as much as Hart, the difference is relatively negligible. Neither are great shooters, but thrive on ball handling, relief, rushing, rebounds and defense.

And as with other free agents, Jerami Grant has already proven himself an integral part of this team, no doubt writing an overtime at some point this season. Drew Eubanks is on a veteran minimum contract, so would be nothing more than a throw-in as part of any trade.

A deadline trade

The blazers are somewhat restricted. As previously mentioned, Winslow’s $4.1 million contract won’t add up to much. We’ve already discussed them Possibility of combining Winslow and Hart in one trade ($17 million total), but it’s probably not the smartest move, narrowing the franchise’s chord.

I don’t really want to speculate on any other potential deals because, to be honest, I’m not sure what $4.1 million gets you. The only thing I will address is a report that suggests the Boston Celtics could still play be interested in Winslow, the player they coveted seven years ago. If that is indeed the case, Grant Williams would be the only player with a similar salary that I would look twice at. But the soon-to-be 24-year-old faces the limited free hand next summer and is likely to face pay.

Free agency

Winslow’s early bird rights mean the Blazers won’t be able to renew him mid-season. This leaves unrestricted agency as the only route they can take to keep it for the long term.

Early bird rights allow franchises to re-sign players regardless of their cap situation. However, it limits the size of the deal to no more than 175 percent of the previous season’s salary, bringing Winslow’s highest salary in 2023-24 with the Blazers to about $7 million.

Or, if it’s higher, and it almost certainly will be, 105 percent of the previous season’s average player salary, which is expected to be around $11 million. The full midlevel exemption is also expected to be a similar amount.

This is where gambling comes in. If Winslow continues to beat his current deal, he may be able to earn more than another team that has actual cap space.

Assessing Winslow’s market outside of Portland is difficult. At this very early stage, the cap space teams will be overwhelmingly the tanking franchises – Utah jazz, San Antonio Spurs, Houston missiles, Detroit piston, Orlando magic, Indiana Pacers, Charlotte Hornets and Oklahoma City Thunder. But there are two others that may be further up the food chain – the Memphis Grizzlies who Winslow has played for but didn’t really enjoy speaking for and the Los Angeles Lakersfinally free from Russell Westbrook’s terrible business.

Just to be clear, I’m not suggesting that Winslow is aiming for anything more than full midlevel exception, but it’s interesting to look at non-Blazer teams that might be able to offer something.


Like I said, I’m a Winslow fan so maybe I’m not the best person writing this. But even the most indifferent Winslow watcher would agree that the Blazers need to make decisions about the Texan’s future in Portland before February.

He seems to like it in Oregonand maybe “find a home” may cause him to choose Portland regardless of the money on offer, and honor the franchise for helping to redeem its worth.

One thing is for sure, Winslow cannot be renewed mid-season, meaning the Blazers will either let him go by deadline or take a gamble and try to re-sign him in July. While the latter is less secure, you must try to hold the big wing simply because it helps this team in a multitude of ways.

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