For months, the Portland Trail Blazers were in a holding pattern as they sought out a Damian Lillard trade that would come close to filling their needs for a rebuild. Trading a franchise star is never easy, particularly when they make clear they have a preferred destination, and even with that aside, you are almost never going to get full value in return for what that player provides.
That was the case with Lillard, but eventually the Blazers were able to get him to open his list of trade destinations up and found a team in the Bucks facing some pressure of their own to keep their superstar happy. With the Lillard trade (and the subsequent Jrue Holiday trade), the Blazers finally hit the reset button and come into 2023-24 with low immediate expectations but plenty of intrigue about their young core and some new additions from this offseason. Here, we’ll grade out their summer of moves starting with the Draft where they hope they’ve landed their new franchise cornerstone.
Draft: A
The Blazers landed the No. 3 pick in the Draft, but ended up with the second-best prospect in the eyes of many after the Hornets chose Brandon Miller over Scoot Henderson due to concerns about Henderson’s fit next to LaMelo Ball. That sends the former G League Ignite star guard to Portland where he ushers in a new era with the departure of Lillard, and will now join a fascinating young backcourt with Anfernee Simons and Shaedon Sharpe. Figuring out how those three work together — and if that trio should be the core long-term — is part of the upcoming evaluation process for the Blazers. Along with Scoot at 3, the Blazers also added Kris Murray (brother of Kings breakout rookie Keegan) with the 21st pick, providing some needed wing help and a 3-and-D type that should be able to contribute immediately. For those selections our Brad Rowland gave the Blazers an A and A- respectively, as they got great value from both pick spots.
In the majority of drafts over the last two decades, Henderson would’ve been the No. 1 overall prospect. With Victor Wembanyama involved, that wasn’t the case in 2023, but Henderson slipping to No. 3 on the board provides incredible value for Portland. Granted, the Blazers may have some interesting decisions to make in the future with Damian Lillard, but Henderson is too good to pass on with this pick.
Portland’s overall direction is quite interesting right now after the selection of Scoot Henderson and how that meshes with Damian Lillard. The selection of Murray works in any context, though, as he is a versatile combo forward that can shoot and defend. Yes, he’s older than most first-round prospects, but that is why he’s available now. It’s a very good value.
Free Agency/Contract Extensions: C+
The Blazers biggest free agency move was resigning Jerami Grant to a massive 5-year, $160 million deal. It was an eyebrow raising deal in the moment that became even more interesting after the Lillard trade request days later. For me, it’s the years, not the annual salary, that’s surprising in this deal, as I’m not sure who they were bidding against to need to give Grant that fifth year when he’ll be 34 and they’re going to have to start extending their youngsters like Sharpe and Henderson. The process there didn’t make a ton of sense, even though I absolutely see the value in having a veteran like Grant on the roster to help their young core. Portland also re-signed Matisse Thybulle, which is again a perfectly fine move to keep a solid defender on the roster you can pair with the young guards, and added Moses Brown, who will likely not touch the rotation now that they have Deandre Ayton and Robert Williams III. Overall this was never going to be a big summer in free agency for the Blazers and they did perfectly fine in bringing back who they did, it’s just the years on Grant’s deal that remain a bit of a mystery to me.
Trades: B
The Blazers may not be done wheeling and dealing this year, as they have taken a Russian nesting doll approach to point guards, trading Damian Lillard for Jrue Holiday for Malcolm Brogdon, who will absolutely be a trade target for contenders either prior to the season or at the deadline should Portland keep him around for the start of the year. It’s fairly clear after the return from Holiday became official that the Blazers did well in the Lillard trade and certainly seem to have gotten more out of it than they would’ve dealing with Miami. Holiday’s value was only raised by the Bucks getting Lillard, and the Blazers were able to ask for a very high price from other East contenders that now wanted an elite perimeter defender to deal with Milwaukee. Boston was willing to fork over Robert Williams III and Brogdon, along with two first round picks, to make that happen. All told, the Blazers netted three firsts, two swaps, Deandre Ayton, Robert Williams III, and Malcolm Brogdon (and Toumani Camara) for Lillard, which is a pretty good haul that could add even more draft assets in the future if they move Brogdon.
That’s not a return that replaces what Lillard provided and probably never will, but given the circumstances, they’ve done well. How you feel about the deal overall likely depends on your belief in Ayton, who they clearly valued as a better fit for their young team than Jusuf Nurkic. I still think Ayton has positive value and can be a particularly helpful player in Portland as a pick-and-roll partner for Henderson. Adding Williams as an elite rim defender is also a big help, and it’ll be fascinating to see how the Blazers deploy their two big men. They should have 48 minutes of good center play — which is somewhat ironic considering that was never the case in the Dame era — but how effective Ayton and Williams can be in two big lineup will likely determine if they can roll with those two long-term or if one (likely Williams) ends up back on the trade block.
Overall this was a wild offseason in Portland that was the culmination of a few years of decline that finally pushed Lillard to ask out — and I’m not so sure the Blazers front office wasn’t relieved by that request. They can now reset everything and try to build a contending roster again, but there are certainly no guarantees they hit the heights of the Lillard era.