The Portland Trail Blazers are trying their best to balance between two different paths. They want to continue competing with Damian Lillard as their leader, refusing to trade their franchise icon. At the same time, they have held onto their recent draft picks and have the No. 3 pick in tonight’s NBA Draft.
At some point, they have to pick a path, and that decision could come as soon as today. The latest intel from NBA insiders is overwhelmingly in support of the Charlotte Hornets drafting Alabama forward Brandon Miller at No. 2, thus leaving G League Ignite point guard Scoot Henderson to fall to the third pick.
This does a couple of things for Portland. First, it increases the trade value of the pick right now; it’s almost a lock that a team trading up will be able to draft Scoot Henderson. They can negotiate with teams and be ready for a deal when they come on the clock.
The other thing that it does is put pressure on Portland. It could draft Henderson, but that communicates to Lillard the franchise isn’t serious about putting a contender around him. If they’re keeping Lillard, the Blazers need to flip the pick for a star; Dame and Scoot aren’t a pairing to win, next season or long-term.
If they’re going to make the trade, which package is the best? Let’s power rank four packages from four different teams rumored to want Scoot, aligning them from “worth taking” to “slam dunk”. We begin in Canada and the potential addition of a two-time All-NBA forward.
Trade No. 4: Raptors claw up to No. 3
The Toronto Raptors were the early team to get into the Scoot Henderson rumor mill, and the reason makes sense. They are at a franchise crossroads, much like Portland is: do they commit to their current core or move the veterans to get younger and retool around Scottie Barnes?
Adding Scoot makes sense for either path, honestly, but especially so if they are going to undergo a youth movement. Their best player is Pascal Siakam, and he would be the centerpiece for their offer for No. 3:
For Toronto, they can pair Henderson and Anfernee Simons in the backcourt with Gary Trent Jr. coming off the bench or flipped to another team. Barnes and OG Anunoby would man the forward spots. That team probably has more balance than the current roster, and it’s a whole lot younger.
The Trail Blazers would get off of the contract of Jusuf Nurkic and would pair Pascal Siakam and Jerami Grant in the frontcourt, with plenty of optionality to play Siakam at the 5. With the No. 12 pick, they could add a wing like Gradey Dick or a center like Dereck Lively II to the mix.
Is it enough? Probably not, considering that Siakam is a shaky shooter (although an underrated passer) and is already well into his prime. Henderson looks like an All-Star lock and could be a Blazer for the next decade; they would need more of an upgrade to make it worth the move.
Trade No. 3: Celtics duck the payday as Blazers add Jaylen Brown
The Boston Celtics have an All-NBA forward in Jaylen Brown that they aren’t sure if they want to keep around. Brown is eligible for a massive supermax contract extension this summer, and if the Celtics pay Brown and then Jayson Tatum next summer, they will owe well over $100 million to just two players. In the era of the second tax apron, that’s a punitive position to be in.
After trading Marcus Smart for Kristaps Porzingis, the Celtics can give their backcourt a makeover by adding Henderson and Simons. They get out of paying Brown, can bring Henderson along behind Malcolm Brogdon and Derrick White, and suddenly have a lot more playmaking juice.
Here’s how it would look:
The Trail Blazers get the two-way wing they haven’t had since…well, maybe Nic Batum? Brandon Roy? For a team that excels at developing guards, they have been a wasteland at small forward, so adding Brown would be a godsend. The Blazers don’t need him to be an elite on-ball creator and dribbler, because they have one of the league’s best in Lillard.
This is a lot to give up for Brown; Simons is a high-scoring guard in his own right, Henderson looks like a future star, with another pick to boot. That’s why this deal isn’t higher on the list.
But Brown is a player the Blazers aren’t going to find any other way, and he’s ready to compete right now. That’s a tempting move for Portland to consider.
Trade No. 2: Portland lands a rising star
The Orlando Magic are a wild card heading into the draft tonight. Armed with the No. 6 and No. 11 picks, they are a threat to trade up or trade down. If they offered a package of 6, 11 and Wendell Carter Jr., Portland likely thinks long and hard about it.
This is another path for the Magic to get up to three to take Scoot, who looks like an excellent fit and the solution to many of their team needs. It’s a painful one, but it involves swapping a player they hit on two years ago to get a player with an even higher upside:
The Magic get to draft Scoot, they get another first-round pick to add a shooting wing, and they will find a way to move forward without Franz Wagner. The deal, pitched by Danny Leroux on an episode of the Dunc’d On podcast, lets the Magic chase MVP upside in Henderson at the expense of two solid starters.
Portland gets an incredibly talented building block at the league’s most important position. Wagner and Grant would be a great pairing on the forward line, and Wagner is young enough to form a young nucleus with Shaedon Sharpe and Simons, even as Lillard ages out.
The Blazers would have a young and talented starting five and could build for contention over the next few seasons instead of pushing all of their chips in for the next season or two.
Trade No. 1: Blazers swing for the fences
Finally, we come to the No. 1 trade on our list, a deal that, without a question, has the highest chance of blowing up in Portland’s face. It also is the only deal on this list that can realistically lead to a championship while Dame is still on the team, which is why it lands as the top deal.
The New Orleans Pelicans are hungry to find their long-term point guard, and at the same time are growing weary of Zion Williamson‘s lack of maturity and discipline. Even while recognizing that he is being dealt at a low point in his value due to his injuries, the Pelicans might just decide the time is right to move on from Zion.
They certainly get a large return, as Williamson’s star power and upside when healthy demand a significant package. Henderson can be the point guard of the future, running the show for a young core headlined by Brandon Ingram that also includes Herb Jones, Trey Murphy III and Dyson Daniels. They can keep Simons and try to move CJ McCollum, or more likely reroute Simons to another team for more draft capital.
Why does Portland do it? Because when he was healthy, Zion was one of the 10 to 15 best players in the league. His package of handling, scoring and explosion are truly special. The Blazers aren’t going to win a title with a low-end All-Star as Lillard’s wingman; they need another star, and Zion would be that star.
It’s an incredibly risky bet, but it has the most upside, and at this point in Lillard’s career, it’s time to swing for the fences. Drafting Scoot and trying to straddle two timelines is playing it safe. The Blazers need to stop being afraid of the risks and take a chance.