The Blazers may have traded Damian Lillard, but they likely are not done yet. As part of the package to get Lillard, the team acquired Jrue Holiday, and the veteran guard represents a chance for the Blazers to receive substantial assets to accumulate talent as their Scoot Henderson-led core grows.
There is “a good chance” Holiday is on the move before Monday, according to The Athletic’s Shams Charania, and the trade market for Holiday should end up being much wider than the one for Lillard. Though Holiday is not as good as Lillard, every team could use a player like him, and his contract status (a guaranteed $36.8 million this season, plus a 2024-25 player option) makes him an attractive target. He also is eligible to sign an extension now, so the team that gets him could lock him in for longer.
Holiday is an All-Star-caliber player who impacts winning on both ends, with a reputation as one of the best teammates in the league. He averaged 19.3 points, 7.4 assists and 5.1 rebounds per game with Milwaukee last season while shooting 48 percent from the field and 38 percent from 3. Holiday’s 3-point shooting has improved in the latter half of his career, as he’s made 39.5 percent of his 3-point attempts over the last three years. He succeeds on the ball as a playmaker due to his drive-and-kick game, as well as off the ball with his catch-and-shoot ability.
Holiday is also one of the league’s premier on-ball defenders. He made first-team All-Defense last season and has made one of the two All-Defense teams in five of the last six campaigns. All told, Holiday finished eighth among guards in All-NBA voting last season, the first year in which he received genuine consideration for the honor.
However, Holiday also is 33 years old and plays a physically taxing brand of basketball. Will he hold up into his late 30s? His shooting improvement helps, and he’s a high IQ player. But over the last three seasons in Milwaukee, Holiday’s efficiency in the playoffs has dropped as opposing teams have made him beat them instead of Giannis Antetokounmpo or Khris Middleton. In those three playoff runs, Holiday shot just 39.6 percent from the field and made only 30.5 percent of his 3s. It would help him to land in a situation where he is not required to create as much of his own offense consistently, particularly late in the shot clock.
Even with his playoff troubles, Holiday is an incredibly valuable player who will command enormous interest. He is the best player who seems to be readily available on the market — with apologies to James Harden, I think a wider swath of teams have more trust in Holiday as a significant acquisition. This allows the Blazers to continue to dictate his trade market.
Before we jump into my six most likely Holiday suitors, a few notes on seven other teams that have reason to get involved.
• Clippers acquire Jrue Holiday
The case for the Clippers: This is the easiest one to lay out: The Clippers are in an all-or-nothing season, with Paul George and Kawhi Leonard on contracts they have yet to extend (both have player options for 2024-25). The Clippers have talked throughout this run about adding players with “Clipper DNA,” and Holiday has that to a ‘T.’ He’s tough, competitive and one of the most talented scrappers in the league. His addition would allow George to take on fewer difficult defensive assignments, potentially keeping the Clippers’ wing healthier. Holiday would give LA a reliable lead guard when Russell Westbrook gets over-aggressive but wouldn’t overtax Holiday with initiation responsibilities with George and Leonard around. Holiday, George and Leonard would also give the Clippers the best defensive perimeter trio in the league, with enough shot creation to hopefully make things work.
Pursuing Holiday makes more sense for the Clippers than their long-reported flirtation with Harden. Holiday fits the Clippers’ needs much better, considering Westbrook is set to play a part as well. Harden can’t play effectively off the ball. Holiday can. That provides greater flexibility for lineups including Westbrook with the dominant George and Leonard duo, who have posted a plus-10.8 net rating in over 2,300 minutes together on the court over the last three years. Given how much Harden likes to dribble, adding him will take the ball out of George’s and Leonard’s hands, which, to me, is a net negative.
Additionally, Holiday’s contract can be extended this season, while Harden’s cannot because he only signed a two-year deal last offseason. The effect of bringing Harden home to Southern California also exists with Holiday, who attended Campbell Hall High School in Studio City and was named California’s Mr. Basketball in 2008.
Does this make sense for the Blazers? This represents the floor of what the Blazers can expect in a Holiday trade. Even if the Clippers don’t actually offer it, I think it’s quite easy for the Blazers to make it seem like they have an offer like this on the table from the Clippers when talking to other teams. It would give Portland two more unprotected picks in exchange for dealing Lillard (bringing their total to three unprotected firsts and two pick swaps), in addition to Deandre Ayton and interesting fliers on Boston and Toumani Camara. They could then try to flip Morris and Covington for picks closer to the February trade deadline. If the Blazers get a better offer than this from another team, they could persuade the Clippers to include Terance Mann in the deal instead of Covington if LA is desperate enough to put all its chips in.
The downside to this deal is that none of those picks would come before 2028, which may not be ideal for general manager Joe Cronin. But he could perhaps flip these further-out picks to a team like the Utah Jazz or Thunder, who may need to clear the deck of some of their excess draft assets coming down the pike sooner. The Thunder, in particular, have a deep roster of young players already and multiple first-round picks in all of the next four drafts. It’s unlikely they’ll be able to use all of those selections.
• Sixers acquire Jrue Holiday
• Clippers acquire James Harden• Blazers acquire Marcus Morris Sr., Robert Covington, Amir Coffey, Brandon Boston, an unprotected 2028 first-rounder from the Clippers; an unprotected first-rounder, second-rounders and a future first-round pick swap from the 76ers.
The case for the 76ers: There would be no bigger home run for Philadelphia than if the Harden nightmare ended with them getting Holiday. He would be an awesome partner for the rapidly improving Tyrese Maxey in the backcourt and is the kind of exceptional drop-coverage defender the 76ers desperately need to build a defense around Joel Embiid. It’s the kind of deal that could avert a disastrous Embiid trade request crisis if the Harden situation doesn’t turn out well. The 76ers should be doing everything in their power to make something like this work.
Does this work for the Blazers? It returns slightly more than the straight deal with the Clippers above. The 76ers also have their own draft picks moving forward, meaning the Blazers could try to extract an unprotected first-rounder from Philadelphia as opposed to only getting picks five years out from the Clippers.
Does this work for the Clippers? While I’d rather have Holiday than Harden and would be willing to give up the extra first-round pick to bring Holiday to LA, getting Harden instead in this potential deal would allow the Clippers to keep that pick to make another trade down the road. If the Clippers don’t see as much of a difference between Harden and Holiday as I do, maybe this works better for them.
• Celtics acquire Holiday
The case for the Celtics: Boston has a two-year window it must maximize before Jayson Tatum’s next contract kicks in and the money owed to he and Jaylen Brown becomes a real burden. The Celtics should be going all-in to acquire players who can help them now. Holiday replaces what Marcus Smart brought to the team defensively while also adding more consistent offensive play. The Celtics could close with a foursome of Derrick White, Holiday, Tatum and Brown, a perimeter group that can defend at an exceedingly high level plus create quality shots offensively. Holiday would also be an awesome fit next to Kristaps Porziņģis in drop-coverage scenarios.
To make the trade math work, the Celtics have to include Brogdon and one of Al Horford or Williams. I opted for Williams because Horford has proven to be more reliable at this stage due to superior health and a more well-rounded offensive game. Williams’ defensive upside is vast, but I don’t love the idea of playing him with Porziņģis, whereas I can envision Horford doing so occasionally. The Celtics would need to make an additional preseason trade to add further frontcourt depth. Maybe they could rope in Oklahoma City as a third team to get one of their surplus youngsters like Jeremiah Robinson-Earl, in exchange for one or two second-rounders.
Acquiring Holiday gives Boston the offensive floor spacing and rim protection it seemed to want from Porziņģis in addition to the perimeter defense of the departed Smart. Remember: The original Porziņģis deal reportedly included Brogdon over Smart, so combining shooting and defense was obviously on Boston’s mind from the get-go.
Does this work for Portland? I think the Blazers will likely get a better offer than this. The Celtics could provide Portland draft picks that are closer to conveying — they own all of their own selections, plus a 2024 Golden State first-rounder — but those picks would not have nearly the same upside as ones from the Clippers or 76ers at the end of the decade. The Celtics are going to be good for a while due to the ages of their core players. Pritchard would be a nice get as a backup point guard, and he’d be an immediate fan favorite as a Portland-area kid. The Blazers might be able to flip Williams and Brogdon later in the season for additional draft capital, but I don’t think either would return much more than late first-rounders, if that, due to their injury histories.
• Heat acquire Holiday
• Blazers acquire Kyle Lowry, Nikola Jović, Haywood Highsmith and two unprotected first-round picks
The case for the Heat: A deal for Lillard would have forced the Heat to give up all of their assets, but a trade for Holiday could allow them to hang onto Tyler Herro, Jaime Jaquez Jr. and/or Caleb Martin, thus maintaining their depth. Holiday would be an awesome fit within the Heat’s culture and would take a ton of pressure off Herro and Jimmy Butler defensively.
Having said that, this would be a substantial enough move to preclude the Heat from putting together competitive offers for bigger stars that theoretically could come available in the future, such as Antetokounmpo or Embiid — at least without including Bam Adebayo. Perhaps there is a case to move Adebayo anyway if Antetokounmpo or Embiid is the return. But is it worth trying to acquire Holiday to maximize this season for Butler and Adebayo if it potentially makes it harder to make a bigger splash in the future? That’s a calculation Miami has to make, as I think this is the minimum price point for the Heat to top potential Holiday deals from the Clippers and 76ers. I’m not totally sold that they would or should do it.
Does this work for the Blazers? If the Heat are willing to top a potential Clippers offer by including Jović and two unprotected first-rounders, then yes, there is a chance this is the best offer. If the Heat are not, they will likely get outbid. The Heat and Blazers could also ask Oklahoma City to give Miami its 2025 lottery-protected first-rounder back for its 2028 first-rounder and an additional asset, while also perhaps slightly diminishing the protections on the 2028 pick. That would allow the Heat to send the Blazers their 2024 and 2026 first-rounders if the Blazers wanted more immediate draft capital.
Still, all of this would be contingent on Miami and Portland putting aside their differences after the contentious Lillard situation.
• Knicks acquire Holiday
The case for the Knicks: I don’t love this one as much as others. I get the idea that acquiring a complementary star like Holiday may make New York more enticing for another superstar in the future. It’s also extremely easy to imagine Tom Thibodeau enjoying Holiday’s defensive attitude and aggression next to Jalen Brunson. The Knicks would immediately become the most miserable team to play in the league with Josh Hart flying around and crashing the glass; Holiday, Grimes or Barrett, Donte DiVincenzo and Immanuel Quickley defending hard on-ball; and Mitchell Robinson and Julius Randle playing physically inside. That team would have a puncher’s chance in a seven-game series against a lot of teams in the East by bogging games down.
But the Knicks are already a miserable team to play against, and I’m not sure they’re close enough to winning a title to invest significant long-term resources into a 33-year-old borderline All-Star guard. Barrett’s upside remains interesting to me, at least. His nine-game playoff run, after struggling in the first two games of New York’s first-round series against Cleveland, was superb. In that stretch, along with aggressive defense, he averaged 21.2 points, five rebounds and three assists while shooting 47 percent from the field, 36 percent from 3 and 75 percent from the line. At 23 years old, I wouldn’t want to give up on him yet, even if his inefficiency and week-to-week shooting inconsistency can be maddening. The same goes for Grimes: He already is a strong two-way starting wing who can knock down shots and defend, which has real value on a rookie-scale deal with two years remaining.
With Holiday turning 34 years old in June, I’m not sure the theory that he’d make the Knicks drastically more appealing for a superstar holds up. To me, acquiring Holiday seems like the kind of “skipping steps” move an old Knicks regime would attempt, as opposed to this new, more patient front office under Leon Rose.
Does this work for the Blazers? Depending on the picks, it could be the best offer available. Barrett would be a fascinating wing scoring option for a Henderson-Anfernee Simons–Shaedon Sharpe core; he fits their age timeline, and his power game offers an interesting complement on the wing to their more skill- or athleticism-based styles. Grimes would also make all of their lives easier as a defensive player who can knock down shots.
But I’m skeptical the Knicks would actually offer this much, given the situation laid out above and the deliberate approach they have taken recently. I think they’d be willing to offer Quickley, given his forthcoming contract talks that will result in him getting paid handsomely by someone (possibly even by the Knicks in the next two weeks). But with Henderson and Simons in tow, Quickley doesn’t make as much sense for the Blazers.
• Warriors acquire Jrue Holiday
Why would the Warriors do this? I can’t imagine a better fit for the Warriors than Holiday. He is everything the organization wants, especially on defense. More than anything, the Warriors need a backcourt player who can shoot and take on tough defensive assignments at the point of attack. Klay Thompson has been great on offense since his return from multiple serious leg injuries but has lost a step on defense and cannot take on the toughest assignments anymore with the same level of success. Holiday would give the Warriors one of the league’s best options there while also providing offensive firepower.
I love Holiday’s potential to play both on and off the ball in the Warriors’ offense. They can use him to run the second unit or use him in sets with the starters that involve running Stephen Curry off some sort of exotic action to get loose for a 3. They can also use Holiday off the ball with the starters and let his improved shooting and quality decision-making thrive. In recent years, the Warriors have had a lot of players in this spot who are good on one side of the ball (Jordan Poole on offense; Gary Payton II on defense). Having all of those skills contained in a single player would give them tremendous lineup flexibility.
To get someone like that, the Warriors will have to give up real value. While some Warriors fans might not be excited about surrendering Kuminga, I think the team’s roster decisions over the past eight months have made it more difficult to imagine Kuminga on the floor in important moments anytime soon. It’s not a bad thing that the team reacquired Payton, re-signed Draymond Green and cemented Kevon Looney’s role, but it becomes hard to construct lineups with enough floor spacing featuring two of those three and Kuminga. That’s a big reason Moses Moody played rotational minutes in the playoffs even though Kuminga closed the regular season well. Warriors brass has spoken highly of Kuminga’s work this summer, so if they feel his shooting has improved drastically, keeping him is the right call. But if it hasn’t, cashing in Kuminga for a veteran like Holiday who would immensely help their championship aspirations makes a lot of sense.
Does this make sense for the Blazers? I think it does. The Blazers should be making as many high-upside swings as possible around Henderson, Simons, Sharpe, Ayton and company. That core with Kuminga would be among the most athletic in the NBA and would provide an exciting product while Portland progresses in its rebuild. The full Lillard package would essentially become Ayton, Kuminga, two firsts, three pick swaps and whatever the Blazers are able to flip for Paul.
If this deal were to occur, my first call as Portland would be to Brooklyn to see if the Nets had interest in taking on Paul while giving up a first-rounder and additional draft capital in exchange for Portland absorbing Ben Simmons’ contract. Paul’s ability to organize an offense would help the Nets this year, considering they have no incentive to tank with their first-rounder slated to go to Houston. Meanwhile, with Portland rebuilding for the next couple of years, taking on Simmons’ deal this year isn’t as big of a deal; then he’d become an expiring contract in 2024-25 that could fetch value in a subsequent move. Portland could turn this into a single three-team deal using the trade exception created from the initial Lillard deal, though that would require the Blazers to take on real money and would put them over the luxury-tax line until the trade deadline, when perhaps they can move Jerami Grant.
While the Warriors deal is my favorite, the easiest answer remains the Clippers. They have enough incentive to get a deal done because it’s hard to envision where they go f they don’t at least make the conference finals. They need to do something to add to their roster, and it makes sense for them to cut out Philadelphia and go after Holiday instead of Harden.
If draft capital is what the Blazers covet, it’s hard to see them doing much better than the two unprotected first-rounders the Clippers can toss in, unless another team decides to add in a high-value young player like Grimes. Even then, the Clippers can include Mann to sweeten the pot.
Other teams can offer more, but the Clippers are the team most likely to be desperate enough to offer everything they can. If they don’t, or if the Blazers decide to play hard ball and try to call the Clippers’ bluff, it’s not impossible that the 76ers step in and pull off a miracle end to the Harden situation.
— This article originally appeared in The Athletic.