Trail Blazers Need To Gamble on Justise Winslow in Free Agency

I’m not a fan of people who say “I told you so.” But, I mean, I did tell you all that Justise Winslow was going to be an important part of this Portland Trail Blazers franchise.

I said it in February, August and October.

Right, gloating out of the way.

Now, the Blazers have a decision to make. And they have until the trade deadline to make it.

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

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

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

And for good reason. Winslow’s team-first focus and ability to competently guard positions one-through-five have made him a revelation off the Blazers bench. Yes, he’s probably not scoring enough to enter the Sixth Man of the Year conversation, but he is everything this franchise has needed from a bigger, athletic, skilful reserve.

Sure, he can’t shoot. But this team has plenty of shooters. The defense, the ballhandling, the passing and the basketball IQ, however, have been priceless since his arrival and more crucially this season as the Blazers sit atop the Western Conference.

Like Draymond Green, the man does intelligent things on the floor. It’s innate, whether it’s a pass, a screen and defensive swipe or a cut, being in the right place at the right time is a skill.

There was a reason the former Duke standout was reportedly worth four Boston Celtics first round picks to Danny Ainge on draft night in 2015. Yes, injury, diminished opportunity and stints of poor form have held him back but natural ability will always find a way to shine through.

Statistically, despite registering a near triple double against the Phoenix Suns on November 4, his season numbers — 7.9 points, 31 percent from three, 5.1 boards, 3.5 assists and 1.3 steals — don’t do his contribution justice. See what I did there.

But Winslow isn't necessarily needed to put up gaudy numbers. His value sits behind statistics, doing all the little things that make his teammates and the team better.

Now, if the Blazers want to keep Winslow beyond the 2022-23 season, there are a few factors at play. Given the nature of his $4.1 million contract, specifically his Early Bird Rights, the franchise doesn’t have the same options it has with other contracted players. We discuss this further down.

Other moving parts

As mentioned countless times before, Josh Hart appears to be the Blazers' best trade chip. He’s capable on both ends of the floor and with his $12.9 million deal this season and likely non picked up $12.9 million Player Option next season, Hart almost certainly has to be on the block.

Cronin has openly said he still has work to do to improve this team and given the franchise’s salary sheet — trade, internal growth and crafty deep draft decisions seem to be the only way forward.

While Winslow hasn’t contributed as much as Hart, the difference is relatively negligible. Neither are great shooters, but thrive on ballhandling, facilitating, hustle, rebounding and defense.

And as for other free agents, Jerami Grant has already proven to be an essential part of this team and no doubt pens an extension at some point this season. Drew Eubanks is on a veteran minimum deal so would be nothing more than a throw in as part of any trade.

A deadline trade

The Blazers are somewhat restricted. As discussed, Winslow’s $4.1 million contract isn’t going to bring back a lot. We’ve already discussed the possibility of combining Winslow and Hart in a trade (a combined $17 million) but it’s probably not the shrewdest of moves, depleting the franchise's wing depth.

I don’t really want to speculate on further potential deals because honestly, I’m not sure what $4.1 million gets you. The only thing I will bring up is a report suggesting the Boston Celtics might still be interested in Winslow, the player they coveted seven years ago. If that actually is the case, the only player at a similar salary that I’d even look at twice would be Grant Williams. But the soon-to-be 24-year-old hits restricted free agency next summer and will probably be expecting to be paid.

Free agency

Winslow’s Early Bird Rights mean the Blazers can’t extend him midseason. This leaves unrestricted free agency as the only path they can go down to hold onto him long term.

Early Bird Rights allow franchises to re-sign players regardless of their cap situation. However, it does restrict the size of the deal to no more than 175 percent of the previous season’s salary, which puts Winslow’s highest 2023-24 salary with the Blazers at about $7 million.

Or, if it’s higher and it will almost certainly be, 105 percent of the average player salary for the prior season, which is projected to be around $11 million. The full Midlevel Exception is also expected to sit at a similar amount.

Here’s where the gamble comes into play. If Winslow continues to outperform his current deal, he might be able to earn more than this from another team that has actual cap space.

Gauging Winslow’s market outside of Portland is tricky. At this very early stage, cap space teams are predominantly going to be the tanking franchises — Utah Jazz, San Antonio Spurs, Houston Rockets, Detroit Pistons, Orlando Magic, Indiana Pacers, Charlotte Hornets and Oklahoma City Thunder. But there are two others that might be higher up the food chain — the Memphis Grizzlies who Winslow has already played for but has not really spoken fondly of and the Los Angeles Lakers, finally free of Russell Westbrook’s awful deal.

Just to clarify, I’m not suggesting that Winslow is going for more than the full Midlevel Exception, but it is interesting to look at non-Blazer teams who might be positioned to offer something.

Conclusion

As I said, I’m a Winslow fan so I might not be the best person writing this. But even the most indifferent Winslow watcher would agree the Blazers have decisions to make before February on the Texan’s future in Portland.

He seems to like it in Oregon, and perhaps “finding a home” may prompt him to choose Portland regardless of the money being offered, honoring the franchise for helping rehabilitate his value.

One thing is for sure, Winslow cannot be extended midseason, which means the Blazers either deal him at the deadline or take a gamble and try to re-sign him in July. While the latter is less certain, you have to try and hold onto the big wing purely for the fact that he helps this team in multiple ways.