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10 Potential Trade Deadline Deals for the Portland Trail Blazers

Let’s discuss how Josh Hart and Justise Winslow could help upgrade the roster mid season.

New York Knicks v Portland Trail Blazers Photo by Sam Forencich/NBAE via Getty Images

The Portland Trail Blazers still “aren’t good enough”. Honest words spoken by the franchise’s General Manager Joe Cronin at his offseason press conference last month. While decent-enough progress has been made in recent weeks, it’s unlikely further upgrades occur between now and the end of the calendar year — unless of course the Blazers get in on the Donovan Mitchell or Kevin Durant sweepstakes.

However, come 2023, the Blazers will no doubt be involved in trade discussions as teams take stock of where they are in the standings. Expiring contracts also become crucial at the deadline with certain franchises looking to get off long-term money, freeing up cap space for the following summer.

Portland goes into this season with a handful of expiring contracts, including Jerami Grant, Justise Winslow, Drew Eubanks, Nassir Little (restricted free agent) and Josh Hart (player option). From all reports, Grant is almost certain to be extended, Eubanks will yield virtually zilch and Little appears to be in the team’s future plans. That leaves Hart and Winslow as pieces the Blazers might use to upgrade at positions of need.

Both arrived in Portland via deadline deals earlier this year. Hart from the New Orleans Pelicans in the CJ McCollum trade and Winslow in the transaction that sent Norman Powell and Robert Covington to the Los Angeles Clippers. Hart is one of those role players who’s as valuable to his incumbent employer as he is to the other 29 franchises, offering playmaking, shooting, defense, rebounding and, from all reports, good vibes.

Great, but the Blazers aren’t struggling for guard talent. Damian Lillard, Anfernee Simons, Gary Payton II, Keon Johnson and Shaedon Sharpe all exist on this roster. Dealing Hart could bring back someone of equal capability at small forward or center. We discussed Winslow’s bona fides last week. Suffice to say he’s a big body on a team-friendly deal that does pretty much everything but shoot from distance. He’s also got some competition at back up power forward with Trendon Watford and potentially Jabari Walker waiting in the wings.

Below are 10 targets the Blazers could pursue using Hart’s $12.9 million and Winslow’s $4 million. Ideally, Cronin is seeking two-way players at the three with multiple years left on their contract.

Three years left

Jonathan Isaac (Orlando Magic), F - $17.4 million

Isaac is one of those high-risk, high-reward talents. The soon-to-be 25-year-old hasn’t played in two years thanks to posterior lateral corner and ACL injuries. Thankfully, we’ll be able to see how he returns when the season starts, before the Blazers make a decision on whether his body is still up to the rigors of the NBA. Isaac is already an elite defender who started showing offensive glimpses before he went down. His injury history might also help the Blazers snag the rangy forward for Hart and Winslow straight up. Any more than that and it might be an overpay. Important note, Isaac’s 2023-24 and 2024-25 contracts are partially/non-guaranteed, giving the Blazers an out if a deal is executed and he doesn’t hold up/play enough games.

Points: 9.3 3-Point percentage: 33% Rebounds: 5.4 Assists: 1.1 Steals: 1.1 Blocks: 1.5

OG Anunoby (Toronto Raptors), SF - $17.3 million

The man the Blazers reportedly chased this offseason could still be had. You’d have to imagine it’d take at least Hart, Winslow and a first to get it done, which means the Blazers will have to remove protections on the pick it owes to the Chicago Bulls next year. Anunoby would fit seamlessly onto this roster, serving as the ideal small forward aside the low-defense backcourt of Damian Lillard and Anfernee Simons. For the Raptors, there’s currently a logjam at the three with the arrival of Scottie Barnes and really only Gary Trent Jr at the two, so Hart slots in nicely next to Fred VanVleet in the Toronto backcourt. Winslow becomes another big body off the bench.

Points: 10.4 3-Point percentage: 37% Rebounds: 4.1 Assists: 1.4 Steals: 1.1 Blocks: 0.5

Two years left

Joe Harris (Brooklyn Nets), SF/SG - $18.6 million

Depending on what happens to Kevin Durant this summer, the Nets might be looking to clear space. Harris is 6’6 and has played more than half his career at small forward thanks to his ability to guard bigger wings. Like Isaac, we’ll have to see how he returns from injury but the Washington State-born wing has a career average of 44 percent from three, which is insane. The 30-year-old almost certainly starts in front of Little at the three, offering depth, defense and shooting.

Points: 11.1 3-Point percentage: 44% Rebounds: 3.2 Assists: 1.6 Steals: 0.5 Blocks: 0.1

Kyle Kuzma (Washington Wizards), PF - $13 million

NBA Champion Kyle Kuzma was probably the best player involved in last summer’s Russell Westbrook trade. Perhaps tainted with that Lakers brush, Kuzma is still a wing capable of playing both forward positions while carrying an acceptable three point percentage. The Wizards currently have both he and Rui Hachimura playing the four, with the Japanese-born talent younger and on a cheaper deal. So Kuzma might actually be available.

Points: 15.6 3-Point percentage: 34% Rebounds: 6.2 Assists: 2.2 Steals: 0.6 Blocks: 0.5

Cedi Osman (Cleveland Cavaliers), SF - $7.4 million

Osman is a Jack of all trades, master of none. You know exactly what he’s capable of and it isn’t bad. Standing a solid 6’7, Osman averages 10.7 points on 35 percent three point shooting. 2.2 rebounds, 2 assists and 0.8 steals a contest. But Portland might need another piece in return if it’s Hart heading to Cleveland, given the current Blazer’s larger pay packet and increased impact on and off the court.

Points: 10 3-Point percentage: 35% Rebounds: 3.2 Assists: 2.1 Steals: 0.7 Blocks: 0.1

Expiring contracts

Bojan Bogdanovic (Utah Jazz), PF - $19.5 million

Getting on in years, the 33-year-old is still an effective NBA player, holding a near 39 percent career three point percentage. There might be some duplication with Jerami Grant but as the Jazz continue the demo of their roster, the Croatian might be one of the pieces that shakes free. The thought of negotiating with Danny Ainge worries me a little though.

Points: 15 3-Point percentage: 39% Rebounds: 3.6 Assists: 1.6 Steals: 0.6 Blocks: 0.1

Harrison Barnes (Sacramento Kings), PF - $18.3 million

Every year Barnes shows up on a list of players the Blazers should target. Similar to Bogdanovic, Barnes does a little of what Grant does. But he may also be of use to the Kings who, dare I say, might actually be good enough to make the play-in tournament this year. Oh, and we’re not sure whether Monte McNair is actually interested in Hart and Winslow. There is, however, the arrival of with Keegan Murray. The number four pick is likely to play minutes at the four this year. Does Sacramento want Barnes blocking Murray’s opportunities? Perhaps the Blazers can help relieve this tension.

Points: 14.1 3-Point percentage: 38% Rebounds: 5.1 Assists: 1.8 Steals: 0.7 Blocks: 0.2

Kelly Oubre Jr. (Charlotte Hornets), SF - $12.6 million

Last summer, Damian Lillard reportedly asked Neil Olshey to go after Kelly Oubre Jr. who eventually ended up with the Charlotte Hornets for more money. Fair enough. But perhaps a Hart for Oubre Jr. deal works for both sides. Hart could start next to LaMelo Ball, pushing Terry Rozier to the bench in a super-sub role. Like Osman, Oubre Jr. offers a little bit of everything while also being able to play the same glue guy role at a position of need for the Blazers. Not sure what the former Kansas standout’s market is next summer, but by then Jody Allen, or whoever owns the Blazers, might be perfectly happy in the luxury tax.

Points: 12 3-Point percentage: 33% Rebounds: 4.3 Assists: 1 Steals: 0.9 Blocks: 0.5

Dillon Brooks (Memphis Grizzlies), SF - $11.4 million

A polarizing figure for some Portland fans but the former Oregon Duck could prove valuable to this roster. Whether the Grizzlies would part with the Canadian is another question with all reports suggesting he’s not only an effective wing on this young energetic team, but a true glue guy and galvanizing presence off the court. Brooks is an above-average defender and has the ability to get hot on the offensive end. I do wonder whether Memphis would want Winslow back in the fold so this would have to be a straight swap for Hart — still think the Blazers can do better.

Points: 14.5 3-Point percentage: 35% Rebounds: 3 Assists: 2 Steals: 1 Blocks: 0.3

Cam Johnson (Phoenix Suns), F - $5.8 million (Restricted)

The Blazers were reportedly interested in the pending restricted free agent earlier in the summer. Nassir Little’s former college teammate and fellow 2019 draftee might also be suffering a lack of court time thanks to teammate Mikal Bridges. In Portland, Johnson would prove a more NBA-ready option at starting small forward over Little. The salary might get in the way here with Winslow not good enough to pry Johnson away and Hart making too much money so the Blazers might have to get creative.

Points: 10.4 3-Point percentage: 39% Rebounds: 3.6 Assists: 1.4 Steals: 0.7 Blocks: 0.3

Quick note: for those clamoring for Jarred Vanderbilt, I honestly don’t think Danny Ainge would part with him for anything less than a first round pick, considering his age and talent so I’m not sure this is a frugal use of the Blazers’ resources.


Josh Hart and Justise Winslow will likely be on the free agent market in roughly 11 months time. Unless Cronin believes them to be crucial to the future of the roster, it’s in his best interests to move the pair for someone that does. Of the two, Hart is probably more important to the Blazers, however he probably has more value to the other 29 GMs so it’ll be interesting to see if he’s still in Oregon after the deadline clock hits zero.

This list of names that might be available six months from now. But as we all know, a lot can change in the NBA in a very short period of time, potentially vaulting other players onto the trade block as the season progresses.

I’ll just finish by adding how refreshing it was to hear a General Manager so openly admit that the team wasn’t good enough. Portland fans have been starved of this type of candor for the past decade. But that candor also demands action. So Cronin will no doubt be on the phones working hard to improve the roster at the deadline, regardless of how the team starts the 2022-23 season.