The 2023 NBA offseason has already been unusual for one reason: the Portland Trail Blazers find themselves at the epicenter of speculation. Speculation about their superstar point guard, Damian Lillard. Mutterings about what Portland’s General Manager, Joe Cronin, will do with the third overall pick in Thursday’s NBA Draft. Whether the Blazers will make the pick and trade Lillard, or maybe they’ll keep Lillard and trade the franchise’s highest overall selection since the infamous 2007 Draft for a veteran or two. Or maybe they’ll keep both Lillard and the pick and call Dame’s “bluff.”
Everything is on the table right now, it feels. As a fan, it’s both exciting and terrifying these fork-in-the-road scenarios. Either the Blazers build a bedrock capable of contending once the current top teams age out (or start that process), or they fall into the hamster wheel of mediocrity that franchises like the Washington Wizards and Sacramento Kings have been stuck in for years. That it took 16 years for the Kings to stop being the Kangzz should tell you how hard it is to drag a team out of that morass once it falls in.
What’s obvious is that Lillard is no longer capable of bringing a team to the postseason all by his lonesome, great though he is. Something must be done to shake things up. Resigning Jerami Grant, taking whomever the Charlotte Hornets leave them between Scoot Henderson and Brandon Miller, and making the kinds of marginal moves that were the basketball hallmark of Neil Olshey’s tenure as President of Basketball Operations will no longer satisfy Lillard, the fan base, or the Blazers themselves.
So what will Portland do? What exactly is on the table here?
Option #1: Trade Damian Lillard and use the third overall pick
For hardcore basketball degenerates like myself, this is the most attractive option. Dame’s value is still very high. He had what some consider to be his best season yet in 2022-23, averaging 32 points per game, five rebounds PG, seven assists PG, with 46-37-91 shooting splits (field goal percentage, three-point percentage, and free throw percentage) while shooting the most free throws per game in his career. 32 is also his career high in PPG.
Creating offense from nothing is a hallmark of a cornerstone player, and Lillard had to turn chicken blank into chicken salad constantly. The basic core of his game is still there, the insane shooting, the pick-and-roll mastery, the capable shot creation, and the willingness (and ability) to go to the rim and challenge the big fellas. He still has the total Point Guard Package that can be the foundation of a top-10 NBA offense.
Lillard’s accolades are legion. Although he never made an NBA Finals or won Most Valuable Player, he has a great argument as the most decorated Trail Blazer ever, with seven All-NBA selections (including a First Team nod in 2017-18), seven All-Star game appearances, a unanimous Rookie of the Year award, and 11 franchise records (including total points). If he plays in Portland next season, he’ll break a few more and become the first Blazer to reach the hallowed 20,000-point total exclusively in a Portland uniform.
Sounds like the kind of guy the Blazers would be nuts to trade, right? Lillard is a franchise icon, the one who stayed healthy, stayed loyal, and stayed transcendent. This isn’t like the situations with Bill Walton or Clyde Drexler. Walton was a broken mess and wanted out of Portland, while Drexler’s viability as a top guy disappeared very quickly after he got emasculated by Michael Jordan in 1992. Lillard’s decline has so far been graceful and is just beginning, and he hasn’t actually asked out of Portland yet.
Even for a colder kind of fan like myself, trading him away makes me feel queasy. I can’t imagine what a more partisan fan would be feeling right now, watching all this buzz and chatter flow back and forth.
Unfortunately, there are a few very good reasons to trade Lillard this summer and why it’ll be more challenging to get good value for him in later years. The two obvious starting points are his age and contract status; Lillard will be 33 when the 2023-24 season tips off in October, and he’s slated to make $45.6 million in Year One of the four-year extension he signed last summer. The numbers after that get increasingly eye-popping, especially once you factor in the new Collective Bargaining Agreement that the NBA and its Players Association agreed upon a few months ago.
The new CBA punishes teams that go over their “aprons” by removing mid-level exceptions, locking on certain roster-building actions, and so on. A detailed look at it will be linked here, but be warned–it’s archaic. With Lillard making $48.7 million in 2024-25, $58.5 million in 2025-26, and having a $63.2 million (!!!) player option in his age-36 season, such an expensive player being on the books is untenable if a team’s draft picks pan out–and those picks also need to be paid.
Health is another concern. While the Blazers were careful to term sitting Lillard at the end of the last two seasons as “shutting down,” the fact remains that Dame has only played 87 games combined in the last two campaigns, being available for slightly more than 50% of contests. Once such an ironman that he led the league in minutes played as a rookie (the only other player ever to do that? Some dude named Wilt Chamberlain), the minutes and hard work might be starting to pile on his six-foot-two, sub-200 pound frame.
Trading for Lillard still would be a great move for some teams, to be clear. His offensive talents are still amazing, and there were a few teams that could have used him in the playoffs that just concluded.
The Miami Heat are one popular hypothetical trade partner. The playoff run they made out of the eighth seed was spectacular. Still, they finally ran out of gas on offense when Jimmy Butler was stymied, Bam Adebayo’s limitations were exposed, and their cadre of undrafted players reminded everyone why they weren’t drafted.
A trade package centered around Tyler Herro (who didn’t play after Game 1 vs. the Milwaukee Bucks due to a broken hand), a Kyle Lowry-Duncan Robinson salary filler pu-pu platter, and as many picks as Cronin can squeeze out of Pat Riley sounds great at first look.
What makes me personally squeamish is that the Heat hardly ever bottom out; even after Butler and Lillard age into ineffectiveness (or leave/get traded), what’s to stop Miami from remaining competitive around Adebayo and decent players around him, and condemning Portland to the bitter fate of turning tons of picks into 11-to-17 draft range choices for the rest of the decade? Bam is still only 25. There’s an extra five-to-eight percent to get out of him from a ceiling standpoint, and Heat coach Erik Spoelstra is the NBA’s resident master at helping players be the best they can be. Maybe trading for Dame gets that extra out of him–possible Dame-Bam DHOs are Viagra to hoop nerds.
Perhaps the New York Knicks would like to make a splash. In one of the more shocking developments of recent NBA history, the Knicks have practiced responsible team-building habits! Stunning, I know!
New York has tons of draft capital, and despite good management from Leon Rose and World Wide Wes, they have a much longer history of terrible management. There’s always the chance that James Dolan, the failson owner of the team and charter member of the Lucky Sperm Club, loses his stuff and fires everybody, trades Jalen Brunson for spare parts and burning tires, and all of a sudden, the Blazers are picking in the top five in 2026 and 2028.
Dolan pressuring Rose and Co. to trade RJ Barrett, salary filler, and the whole damn farm for Lillard is an outcome that is possible, sure. Rose, however, surely paid attention to the Lillard-CJ McCollum backcourts of recent memory, especially to how defensively FUBAR they were. He and his team won’t want to recreate that dynamic with Lillard and Brunson; Mitchell Robinson might blow out his knees trying to cover for both of them on D.
The Philadelphia 76ers were floated around, but the Washington Wizards’ star guard, Bradley Beal, might be a more realistic trade target for them. The Tobias Harris expiring contract, Tyrese Maxey, and the dregs of Philly’s draft capital is not enough for Damian Lillard. The only way this happens is if Lillard tells the Blazers to send him here.
The Boston Celtics, Dallas Mavericks, Brooklyn Nets, and other fringe trade partners are even farther away from trading for Lillard than the Sixers. But what about trading the No. 3 selection for help for our hero Dame?
Option #2: Trade the third overall pick and keep Damian Lillard
This is another option, one with some surprising juice. Apparently, the New Orleans Pelicans are desperate to draft Scoot Henderson, the explosive point guard prospect out of the G League. If the Charlotte Hornets take Brandon Miller, the six-foot-nine wing player out of Alabama, at number two, the phone calls that Pels boss David Griffin places to Cronin over the following weeks would definitely be over 9,000.
Given that New Orleans’ first overall pick in 2019, Zion Williamson, is apparently set on eating himself out of the league (and creating tons of baby mama drama) after signing a $200 million-plus extension last summer, the Pelicans being desperate for a new tentpole superstar is very understandable. The question is, who will fool themselves into trading for this guy?
When available, Williamson is, without exaggeration, the Evolutionary Charles Barkley. A physical presence almost without equal, with efficient production and the potential to be a top-20 guy that ever played, the kind of player that can help a multi-time NBA champion squad. The first two words of that paragraph, when available, have been the main issue–until recently.
I also want to say to anybody that says to err on the side of talent and give the Pelicans Scoot, Grant, and assorted rubbish for Zion, or to fans of other teams that would advocate trading for him: what incentive does this filthy slob have for turning his career around? What motivation does he have to stop wrecking his body with an over-torqued appetite or other people’s lives with an over-torqued libido?
The dude already got paid by the toothless Pels and has shown no inclination to listen to anybody’s criticisms or advice. A man-child reminiscent of the kinds of tools and thugs I grew up watching waste their talents in the NBA at the turn of the century; Williamson and Ja Morant being the first star talents of the Zoomer Generation would make me fear for basketball’s future if David Stern and Adam Silver after him hadn’t done such a great job growing the game overseas and in Canada. We’ll probably have to get used to not medaling in basketball after 2032.
Anyway, that’s why the Blazers trading for Williamson is a stupid idea, though I imagine Voodoo Donuts and Portland’s curvy strippers would be very excited for that to happen.
Other trade partners don’t have the kinds of talent that would vault the Blazers to contending status by trading the third pick. The Nets and Mikal Bridges? The Phoenix Suns and Deandre Ayton? The Indiana Pacers and Myles Turner? The Atlanta Hawks and either John Collins or (gulp) Trae Young? The Toronto Raptors and either Pascal Siakam or OG Anunoby? Giving up No.3, No. 23, and Anfernee Simons for any of those players will not move the needle toward title contention.
Speaking of title-contending, this path might get the Blazers closer to that goal than trading the third overall pick:
Option #3: Keep the third pick AND Damian Lillard, and keep everyone else except Jusuf Nurkic
(Getting this out of the way: in no way, shape, or form is Nurkic a valid starting caliber NBA big right now. Drew Eubanks looked like a better option for much of the season. Sloughing off that contract, which pays him between $16 million and $18 million over the next three seasons, would be a nice way to stay under the tax aprons. Maybe a swap with Miami for Duncan Robinson, with a pick thrown in by Portland to sweeten the deal?)
A caveat is that this path is only valid if the Hornets pick Henderson and the Blazers take Miller. Playing Scoot and Dame together is a non-starter, in my opinion; you’re not drafting a talent like Henderson to be an Aaron Rodgers-style understudy for a few years, and Lillard won’t take kindly to spending the last of his prime years tutoring his replacement.
This path, or a version of it, was suggested by ESPN’s Zach Lowe on his The Lowe Post podcast a few days ago, and I have to admit, it’s grown on me. While I’m doubtful that Joe Cronin and Chauncey Billups can pull it off, it’s a nice splitting of the difference between keeping a franchise icon to the bitter end Kobe Bryant-style and detonating the roster to start again with Simons, Shadeon Sharpe, and whoever is taken at three on Thursday.
How would a rotation of Lillard, Jerami Grant, Simons, Sharpe, Miller, Matisse Thybulle, Duncan Robinson, Eubanks, Random Center X, and either Nassir Little or the rookie was taken at 23 this year do in the Western Conference next season? Maybe not as severely as one might think. While the Denver Nuggets are set up to crush everybody shortly, the other Western teams have significant questions of their own.
Phoenix has the dual Chris Paul and Deandre Ayton issues hanging over their heads, as well as how they can put the kind of roster around Devin Booker and Kevin Durant that won’t require those two to go Zeus and Poseidon on the league to have a chance. Their new governor is also hellbent on channeling 2000s-era Mark Cuban and making an ass of himself.
Sacramento still needs a few scars and maybe another veteran that isn’t Harrison Barnes. The LA Clippers are never healthy. The Other LA Team can’t count on LeBron James and Anthony Davis being relatively healthy for two straight months together again. The abyss is starting to look back at Golden State. Minnesota has stupid basketball players. Oklahoma City has newborn basketball players. We went over New Orleans’ issues above.
If Portland’s issues can be mitigated better than the other teams, and if they get some injury luck, one last deep run with Dame at the helm might be possible if finishing in the Western Conference Finals again is a result he’s willing to risk. Funnily enough, he just might be; Lillard is a smart dude, and there are rumblings that he hasn’t explicitly asked out of Portland because he realizes the team trading for him might have to cripple their own roster to acquire him. Dame might be overrating Cronin’s negotiating skills here, but if Dame thinks that, asking him to accept taking this third path might be more feasible than initially thought.
This is an exciting and terrifying time to be a Trail Blazers fan. The unknown can often be both of those things. One thing’s for sure, it’ll definitely be interesting–and that’s all a fan can really demand of their hometown team in the end.
