And we're off
The Trail Blazers kicked off their offseason transaction cycle with a massive trade. Which is also a massive bet on Scoot Henderson.
Monday night marked the end of an era for the Portland Trail Blazers.
They traded Anfernee Simons to the Boston Celtics, ushering out the final member of the 2019 Western Conference Finals run. ESPN broke the news late on Monday night that Simons was traded, along with two second-round picks, to the Celtics for Jrue Holiday.
Holiday, you may remember, was on the Blazers for just over three days in 2023 following the Damian Lillard trade. The Blazers sent him to Boston, where Holiday became the missing piece for the Celtics on their run to the 2024 NBA Championship.
This time, according to Sean Highkin of the Rose Garden Report, they plan to keep Holiday around.
While there has been a lot of analysis about the financial ramifications of the trade, it would be wise to hold off on that for at least a few days. The Kevin Durant to Houston trade cannot officially be completed until July 6, and it’s very possible this move gets folded into that deal, or perhaps another deal that has yet to be reported. The order of operations matters in these NBA mega deals, so it would be wise not to treat this entire trade as complete or overindex the financial impact of the trade as of right now.
Adding to more fuel to this, the day before the Durant trade, The Ringer’s Zach Lowe said there was a lot of Jrue Holiday smoke in connection to Durant rumors as a potential multi-team deal.
While we still have yet to hear from the Blazers brass about their plans for the team, we likely won’t hear any specifics from them until after the first days of free agency. But by bringing in an aging veteran who has seen his minutes per game steadily decline in Holiday, it allows them to have an easier succession plan to give Scoot Henderson the keys to the offense.
Trading for Holiday is undoubtedly a win-now move, giving Portland another dogged defender to add to their defense-first identity, even at this stage of his career. Holiday has also been an above-average 3-point shooter his entire career, improving from distance as he’s aged, shooting a cumulative 39% from distance throughout the last five seasons. But at 35 years old, coming off an injury-plagued season, Holiday likely cannot play consistent starter’s minutes and still avoid injury. Last season, he missed most games since the 2014-15 season.
If the Blazers made this trade and Henderson doesn’t start on opening night, then I have a lot more concerns about the team’s decision-making apparatus. If this is the move I think it is, a move made to make Scoot the starting point guard, then this is the exact kind of move they needed.
As I wrote in the last newsletter, the Blazers’ offensive rating was +6.9 points per 100 possessions better with Scoot on the floor, the highest on-court differential on the team. If Henderson has another poor start to the season, Chauncey Billups likely won’t hesitate to make the switch. But going into opening night, there’s no reason to keep Henderson out of the starting lineup.
In 10 games as a starter last year, not only were Henderson’s stats better across the board, but the Blazers were also better, going 6-4 in games where Scoot started. While Simons’ 3-point shooting is an asset to an offense, passing the ball, getting your team organized, and getting to the free-throw line are other ways to improve your team’s offensive output. Henderson did that last year in limited opportunities, so there’s very little reason to gatekeep him from doing more of that in a bigger sample size.
At this point, if he doesn’t start despite the eye test improvement and the statistical evidence showing that the Blazers were a better team with Henderson, what exactly are the Blazers doing here?
Nevertheless, there’s more work for Cronin and the front office to do before we can talk more in-depth about where this roster is and how they should approach it. With the 11th pick, as well as the Jerami Grant question, there are a lot of moves still left for the Blazers to make before we can truly analyze the roster.
And to address the remaining three years on Holiday’s contract, his contract is only slightly more expensive than what Simons wanted in an extension (around $30 million average annual value), making the financial concerns somewhat of a moot point. Also, with Deandre Ayton’s current contract expiring at the end of next season, Portland should have cap flexibility next offseason to absorb Holiday’s deal and sort out extensions for players like Toumani Camara and Shaedon Sharpe.
For months, I was selling myself on significantly worse returns for a Simons trade. If he even got traded at all. I had mostly resigned myself to thinking he would never be traded, but I let myself wonder about trades like Jonathan Isaac, Cole Anthony, and the 25th pick in the draft from Orlando, thinking it could be a get out of jail free card. That the Blazers ended up with a two-time champion who played 30 minutes a game on a 60-win team, who just last summer won an Olympic gold medal, is a major come-up from that reality. And to me, the 2nd round picks they sent out are not a material concern. 2nd round picks can be bought anytime.
We all know Portland doesn’t attract NBA free agents, so what were they going to do if they had let Simons walk, or worse, signed him to an extension knowing that extension talks are coming for Camara and Sharpe this summer, as well as Scoot Henderson next summer? Also, selling the 35-year-old Holiday on the back-end of his career on a bench role is a much more tenable ask than it would be to ask a 26-year-old Simons to do the same. Not to mention that there is already some amount of goodwill between Holiday and the Blazers after the Blazers sent him to Boston, which came with a championship ring and a contract extension.
Simons’ role in Blazers history will likely be most remembered for his unlikely 37-point outburst in the 2019 season finale, ruining management’s plans to lose the game in hopes of avoiding the Russell Westbrook and Paul George-led Oklahoma City Thunder. Ruining the plan was the best thing that happened to the Blazers, because it matched them up against a flawed and injured OKC team. They beat OKC and then beat Denver on their way to the first Conference Finals birth since 2000. His game-winning hook shot against the Phoenix Suns in the 2022-23 home opener was another one of his best moments.
Simons was in a no-win situation when Lillard left town and the Blazers drafted Henderson, and it’s impossible not to empathize with him. If the Celtics don’t move him in another deal, he projects to have a monster season in Joe Mazzulla’s 3-point crazy system that many refer to as “Mazzulla Ball.” Without Jayson Tatum, the Celtics badly need another shot-creator, and Simons fits the bill.
So salute to Simons for a great run in a Blazers uniform, lasting longer than most and having a major impact on the team’s best playoff finish since the turn of the century. He also became a pretty candid interview over the years as he grew into his voice, so he will be missed on that front as well. Not that you care about that part.
However, it was time for the Blazers to move on and figure out what they truly have in Henderson, Sharpe, and their other backcourt prospects.
Stay tuned. Things are just getting started.