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The Portland Trail Blazers sit in the middle of the Western Conference with the worst part of their schedule arguably in the rear-view mirror. While the past couple of weeks have been disappointing, their 17-16 record places them on par or ahead of where the majority of pundits initially foresaw the team by Christmas.

But there’s still a lot of work to do to get this team into serious championship contender status.

The Blazers also face the conundrum of three pending expiring contracts in Jerami Grant, Justise Winslow, and Josh Hart (player option). Grant is likely to be extended in January, however the jury is out on Winslow and Hart’s respective futures with the franchise.

The contracts and the quest to improve the roster makes the February 9th trade deadline an important milestone. General Manager Joe Cronin has previously indicated his office’s future plans to push all chips in. But whether all those chips are pushed in at the deadline or in the offseason, remains to be seen.

For any large-scale deal, the first thing Cronin needs to do is get on the phone to Marc Eversley at the Chicago Bulls and negotiate the removal of the protections on the first round pick owed to the Illinois franchise this coming off-season.

It’s a gamble though. If the Blazers do this and then freefall down the standings after the deadline, they potentially cost themselves a chance at a generational talent in Victor Wembanyama.

But if they’re brave enough to remove the protections, it frees Cronin to deal future picks. I’m not sure whether the Blazers get anything of real value back in negotiations with Chicago. I guess it depends on how badly the Bulls think the rest of the season goes for the Blazers.

But, hey, let’s say Chicago is prepared to part with a second round pick and Goran Dragic, who can slot into one of the Blazers’ two remaining trade exceptions — $6.5 million generated in February’s Clippers deal and $3.2 in subsequent Utah Jazz trade.

If both parties agree, the Blazers will be able to trade future first rounders. Obviously, the 2024 pick can’t be dealt due to the Stepien Rule, however picks swaps can still be negotiated.

Once this is done, which teams are under-performing against initial expectations and might want to offload players that might be of value to this Blazers team? I’m not going to spell out specific deals. Instead highlight players and picks that might be needed to secure said player.

OG Anunoby

Despite Scottie Barnes’ stunning 2021-22 Rookie of the Year performance, the Raptors appear to have gone backwards this season. But President of Basketball Operations Masai Ujiri is no fool. If Toronto decides to move out its championship winning veterans, they won’t come cheaply.

We have a pretty good sense that the Blazers asked about OG Anunoby over the summer, falling short of the reported ransom requested. Anunoby, 25, is earning between $17 and $19 million a season over the next two a bit years (including a final year player option) and is the archetypal modern day, two-way small forward.

Every team should want this type of player, a player that should have been taken by teams picking just outside the lottery in 2017. That Zach Collins pick still hurts. Anunoby is an elite defender and, placed alongside Jerami Grant presents one of the most formidable defensive forward duos in the league.

Career numbers – 11.1 points. 36 percent from three, 4.3 rebounds, 1.5 assists, 1.2 steals.

What are you giving up? For Anunoby, Ujiri likely demands nothing less than a couple of players, perhaps a veteran that can be moved again for further assets, say Josh Hart, one or two young players, perhaps Keon Johnson, and one or two first round picks.

Pascal Siakam

Siakam, 28, is a different proposition. Earning $35 million this season and $37 million the next requires the Blazers to send back more salary/players to ensure the legality of the deal. The NBA champion, All Star and Most Improved player recipient also plays on both ends of the ball, however offers more of an offensive punch compared to his small forward counterpart.

Career numbers – 16.2 points. 33 percent from three, 6.4 rebounds, 3.3 assists, 0.9 steals.

What are you giving up? Jusuf Nurkic needs to be included in this deal to ensure salaries can get close to matching. From here, it gets tough. You might have to send Shaedon Sharpe home to Canada. Siakam is the kind of player that demands that kind of return because with him, Lillard, Simons and Grant, you’re cooking. Hart goes too, as well as a first rounder. Cronin would also need to consider roster balance as both Siakam and Grant play the same position and now you have no starting center, but i think you can work around this.

DeMar DeRozan

The Bulls have plummeted in the Eastern Conference, despite being in win-now mode before a ball was jumped. They’re paying DeMar DeRozan, Zach LaVine and Nikola Vucevic more than $86 million. Ouch.

Dealing with the Bulls could be particularly convenient for Portland as it could use the removal of those pick protections discussed above as part of its offer.

I’m not really interested in either of LaVine or Vucevic’s bloated contracts but Siakam and Anunoby’s former teammate DeRozan, 33, is another story. The five-time All Star is earning $27 million this year and $28 million next year. He is close with Damian Lillard and if we learnt anything about the Grant deal with Detroit, Dame likes playing with his friends. Adding DeRozan would solidify the Blazers as one of the best offenses in the league. Yikes, Lillard, Simons, DeRozan Grant. But it doesn’t do a whole lot for the squad’s already lowly defense.

Career numbers – 25.9 points. 29 percent from three, 4.4 rebounds, 3.9 assists, 1 steal.

What are you giving up? For DeRozan, the Blazers remove the protections on its 2023 pick and throw in its 2025 first rounder. Along with the picks, Josh Hart, Justise Winslow, Nassir Little and Keon Johnson make their way to Chicago. This sends the Blazers into the tax with three roster spots to fill. Not sure it happens but it’s an interesting thought exercise.

Kyle Kuzma

I really do feel sorry for Wizards fans. That franchise is the very definition of mediocrity. The DC squad is floundering outside Eastern Conference Play-In picture.

Washington picked up Kuzma in the deal that got Russell Westbrook off their payroll. A solid improvement but still not enough to get them into the relevance conversation. The 27-year-old Kuzma has thrived after escaping LeBron James’ shadow, contributing at both forward positions — another player that could have been taken with the Blazers two first rounders in 2017.

Career numbers – 16.1 points. 34 percent from three, 6.3 rebounds, 2.3 assists, 0.6 steals.

What are you giving up? In this scenario, we’re trading former teammates, selected in the same draft, who are both on expiring deals — subject to a player option. Josh Hart goes home to DC and Kuzma lands in Portland. Hart earns $40,000 less than Kuzma so the money is almost perfect. Heck, the Wizards can have a second round pick for their troubles.

John Collins

Something is rotten in the state of Georgia. I don’t know what’s going on with the Hawks but there seems to be issues between Trae Young and coach Nate McMillan. It doesn’t help that a team that made the Eastern Conference a couple of years ago seems to be stuck in Play-In range, even after offloading most of it draft capital for Dejounte Murray this summer.

John Collins seems to have been in trade rumors for at least two, almost three, years. He is a dynamic, athletic offensive bad man who isn’t as bad on the defensive end as some might think. Another 2017 draftee, the 25-year-old was also rumored to be on the Blazers’ radar during the offseason. They instead chose Jerami Grant, wisely. But, in the unlikely case the Blazers can’t get a Grant extension done in January, I’d perhaps have Collins there as a back up. They can’t co-exist on the same team through skills and position duplication. Collins is contracted through 2025-26 at between $23 and $26 million with the final year a player option.

Career numbers – 16.2 points. 36 percent from three, 8.3 rebounds, 1.5 assists, 1.3 blocks.

What are you giving up? It’s Collins for Grant and some sort of draft compensation back to Portland. Again, unlikely because I’m confident-ish Grant extends with the Blazers.

De’Andre Hunter

Hunter is less likely moved by the Hawks, but if the season continues to trend south, it’s definitely worth a try. When he’s not injured — playing 165 games in three and a bit seasons — he’s a genuine two-way small forward. Taken with the fourth pick in the 2019 draft, the 6’8 Hunter is able to do a little of everything on both sides of the floor at a position of desperate need for the Blazers. They might be taking a gamble on the 25-year-old’s durability in the hope that can find consistency with the Blazers. And there is also a poison pill consideration with the former Virginia star signing his rookie extension before the start of the season. However, if that gets worked, he’s earning between $20 and $24 million over the next four years.

Career numbers – 13.5 points. 36 percent from three, 4.1 rebounds, 1.5 assists, 0.7 steals.

What are you giving up? This is honestly a pipe dream, as I doubt the Hawks give him up. The poison pill situation probably means a third team needs to get involved but even then it’s a slog. Let’s say it’s the New York Knicks who get Josh Hart and Aaron Holiday. the Blazers get Hunter and Cam Reddish and the Hawks gets Nassir Little, Justise Winslow, Miles McBride, Jericho Sims and two Portland firsts. I know it’s messy, I might just move on.

Players on teams we all thought were going to be bad from day one

I won’t spend too much time here because many of these names have been mentioned in trade rumors not just for the Blazers but right across the league over the past couple of months.

Orlando Magic

Mo Bamba, 24, is 7 foot tall with a 7’10 wingspan. He’s probably the ideal backup to Nurkic and while I do enjoy watching Drew Eubanks, he just doesn’t have the size to play the five. Bamba is a rim protector and a floor spacer, opening up all kinds of opportunities for teammates to get to the rim. He’s locked into $10.3 million this year with a non-guarantee deal for 2023-24. So hear it is. Justise Winslow and Nassir Little for Bamba straight up.

Indiana Pacers

Over the past 12 months, Myles Turner has been included in more trade-related tweets than any other Pacer before him. Suffice to say, the Blazers will be coughing up Jusuf Nurkic, Keon Johnson and at least one first rounder for the Indiana big man.

Utah Jazz

Yes, we know they started strong but they’re coming back to Earth. Jarred Vanderbilt was discussed earlier this month, so I’ll just re-iterate what I said then. It’ll take a first rounder and either (1) Justise Winslow, or (2) Keon Johnson and one of Trendon Watford or Drew Eubanks.

San Antonio Spurs

Jakob Poeltl is the only name I’d seriously look at here. While the trade is lopsided, the Spurs have space to take on more money. Similar to Myles Turner, Nurkic, Johnson and a protected first rounder would work here. This might be a little high but it appears the market for the big Austrian is crowded.

Charlotte Hornets

PJ Washington is set to hit restricted free agency next summer and we’re unsure whether the Carolina franchise is ready to pay up. Nassir Little and a couple of second-round picks might get it done. There’s also Kelly Oubre Jr. who we know Lillard likes and he does work positionally, but I’m not sure I’m prepared to offer something like Josh Hart for the expiring up and down wing.

Detroit Pistons

The Blazers were this week linked to Nerlens Noel. Meh. But if the Pistons were willing to include Saddiq Bey who might be gettable after being demoted to a bench role this season, then I’m interested. Something like Josh Hart and Keon Johnson works for me as it addresses Portland’s needs at wing and back up big.

Conclusion

The Blazers need to work themselves out of their current funk. Sure, they keep their first round pick this year if they dip back into the lottery, but I get the sense this isn’t the plan. Cronin seems focused on upward movement after last season’s tankathon.

The above summary is nothing more than observations from within my own skull so please take none of it as official scuttlebutt. It’s obviously important to be aware of the state of other teams around the league, particularly those franchise’s whose seasons have nosedived after initial expectations were high-ish.

I don’t expect you all to agree on the players or the proposed packages put forward. All I’ll say, is that I don’t envy Joe Cronin’s job over the next six weeks as he tries improve this roster, not just for this season but over the next few years.

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