Jrue Holiday Rumors | Hoops Rumors

Holiday Willing To Play Any Position For Blazers

July 29th, 2025 at 6:12pm CST by Dana Gauruder

Point guard Jrue Holiday believes he can co-exist in a backcourt pairing with Scoot Henderson. Holiday, who was traded to the Trail Blazers by the Celtics in June, is projected as the starter alongside Shaedon Sharpe with Henderson likely playing a sixth man role.

“Scoot is aggressive,” Holiday said, per Sean Highkin of The Rose Garden Report. “How he gets to the basket is amazing. Me being able to space the floor and shoot the three is something that will help him out. Being able to play off him and knowing that Scoot is the next one up and [helping him] showcase what he can do.”

Holiday doesn’t want to be pigeon-holed as a one-dimensional guard.

“I think I play every position,” he said. “I’ve proven that and shown that throughout my career. I’m a complete basketball player. You can’t put one position on someone, the way the game is changing now. Guys who have never played point guard are coming into the league and playing point guard. I’m a good fit with anyone.”

Holiday’s contract was the main reason for the deal. Boston was looking to shed salary and Holiday will make $32.4MM next season and $104.4MM in total over the next three years.

Holiday is going from a perennial contender to an organization trying to get into the postseason. He’s hopeful Portland can take that step next season.

“[I’m coming in] not just help out as much as possible, but try to win,” he said. “They have a great coaching staff that have done a lot, and a Hall of Fame coach in Chauncey (Billups). But I think as a current player who’s been through it not too long ago, as far as going through the struggle to win a championship, I still have that feeling and that itch. I’m closer to what that feeling is and how hard it is to actually win.”

Holiday won a championship with Boston with a big assist from Portland’s front office. The Trail Blazers acquired Holiday from the Bucks two years ago in the Damian Lillard trade. GM Joe Cronin then traded him to the Celtics. Holiday was grateful that the Blazers made that move and he’s willing to do whatever the organization asks of him.

“I really appreciate what they did for me the first time around. That really does mean a lot for me and my career,” he said.

Where Holiday fits in beyond this season remains to be seen. Lillard re-signed with the Blazers on a three-year deal after being waived by Milwaukee. He’ll spend the upcoming season rehabbing an Achilles tendon tear. Holiday would actually relish the opportunity to play with Lillard next season if he gets the chance.

Celtics Notes: Lillard, Starting Lineup, Davison, Gonzalez

July 26th, 2025 at 6:12pm CST by Arthur Hill

The Celtics were reported as a potential landing spot for Damian Lillard after he was waived and stretched by Milwaukee, but Lillard never gave serious thought to joining anyone but the Trail Blazers, writes Brian Robb of MassLive. At an introductory press conference this week in Portland, Lillard expressed his excitement over returning to his former team and mentioned a recruiting effort by Jrue Holiday.

“As soon as I was waived and obviously [Jrue] knows that I live here and built my home here and stuff,” Lillard said. “He sent me the eyeball emoji. I kind of knew already like — I already knew where I was pivoting to when he sent it but I didn’t want to say nothing too soon, so here we are.”

Although Lillard isn’t expected to play this season while recovering from a torn Achilles, he could have been an intriguing long-term investment for Boston once Jayson Tatum returns from his own Achilles injury. However, Robb points out that the Celtics couldn’t have come close to matching the three-year, $42MM deal Lillard got from the Blazers. They are currently limited to the $5.685MM taxpayer mid-level exception, and using that exception would have required other moves to get far enough below the second apron.

There’s more from Boston:

In a mailbag column, Robb projects Neemias Queta to be the Celtics’ starting center on opening night if the current roster remains in place. Jaylen Brown and Derrick White are the only certain members of the starting five, and Robb expects the other two positions to come down to decisions between Payton Pritchard and Anfernee Simons, and between Sam Hauser and Georges Niang with Josh Minott as a possible wild card.
This week’s release of JD Davison was a result of him not showing sufficient NBA potential during his three years with the organization, Robb adds in the same piece. He puts the chances of Ben Simmons being signed to fill the open roster spot at “10-20%,” stating that the former No. 1 overall pick will likely get better financial offers elsewhere.
Spanish basketball legend Rudy Fernandez offers a ringing endorsement of Celtics’ first-round pick Hugo Gonzalez, per Zack Cox of The Boston Herald. Fernandez watched the 19-year-old shooting guard develop from a young prospect into a regular contributor with Real Madrid. “I always tried to instill in him the idea of committing to improving the team whenever he’s on the floor, and he’s done that perfectly,” Fernandez said. “He’s got the physical tools, good hands, a strong understanding of the game on both ends, and he’s a solid standstill shooter. Maybe he could improve his movement shooting, especially coming off screens, but he’s the type of player who gets better every day.”

Lakers Notes: Doncic, Smart, Vanderbilt, Kleber, More

July 21st, 2025 at 8:56am CST by Luke Adams

“External fretting” about whether or not Luka Doncic will make a long-term commitment to the Lakers has subsided significantly in recent weeks, according to Marc Stein of The Stein Line (Substack link), who says the star guard and his camp have worked closely with the front office this summer as it has bolstered the roster in free agency.

As previously reported, Doncic played a major role in the Lakers’ efforts to recruit both center Deandre Ayton and guard Marcus Smart to Los Angeles. According to Stein, Doncic’s pitch to Smart “particularly resonated” with the former Defensive Player of the Year, who ultimately chose the Lakers despite the division-rival Suns making a “determined push” to land him.

As of August 2, Doncic will be eligible to sign an extension that could be worth up to a projected $222.4MM over four years. While there’s no guarantee he’ll sign for the maximum four years or that he’ll get a deal done immediately on Aug. 2, it seems increasingly likely that the five-time All-Star will have a new extension in hand before the 2025/26 season begins, as reporting over the weekend indicated.

Here’s more on the Lakers:

Like Doncic, Smart has been working hard this offseason on his body and his conditioning, according to Stein, who writes that the Lakers are optimistic about getting a “sleeker” version of the 31-year-old next season after he battled health issues over the past couple years.
Stein has also heard that forward Jarred Vanderbilt is healthier now than he was at any point during the 2024/25 season. Although both players were on last season’s roster, healthy versions of Vanderbilt and big man Maxi Kleber could feel sort of like offseason additions for the Lakers, Stein writes. Vanderbilt played a very limited role in 36 regular season outings last season, while Kleber didn’t make his debut as a Laker until the playoffs — both of them missed time while recovering from foot surgery.
People around the league believe Trail Blazers veterans Jrue Holiday and Robert Williams are potential trade targets to watch for the Lakers this season, according to Grant Afseth of Fast Break Journal. I’m skeptical of the Holiday fit, given that Los Angeles has shown no interest in taking on long-term money (Holiday is still owed $104.4MM over three years) and Portland was prepared to give up a pair of draft picks along with Anfernee Simons to acquire him (those two second-rounders ultimately weren’t included due to minor concerns about Holiday’s physical). However, if he proves he’s healthy, Williams might make some sense for the Lakers due to their limited depth behind Ayton in the middle.
In case you missed it, the Lakers waived both Jordan Goodwin and Shake Milton on Sunday in order to create the cap flexibility necessary to sign Smart using their bi-annual exception.

Blazers, Celtics Finalize Holiday, Simons Trade Without Draft Picks

July 7th, 2025 at 12:40pm CST by Luke Adams

The Trail Blazers and Celtics have officially completed their trade sending Jrue Holiday to Portland and Anfernee Simons to Boston, according to a press release from the Blazers.

However, the terms are slightly different than what was reported last month. Portland had originally agreed to send the Knicks’ 2030 second-round pick and the Blazers’ own 2031 second-rounder to Boston, but those draft assets are no longer in the deal, which is now a straight one-for-one player swap.

Aaron Fentress of The Oregonian hears from a source that a review of Holiday’s medicals prompted the Blazers to alter the initial terms of the agreement.

There wasn’t enough concern on Portland’s end to nix the deal entirely, Fentress explains, adding that the veteran guard is considered healthy and is working out this summer in preparation for training camp in the fall.

As a result of taking back more salary than they’re sending out in the trade, the Trail Blazers are now hard-capped at the first tax apron for the rest of the 2025/26 league year.

The Celtics, meanwhile, have officially completed both of their major offseason trades on Monday, having also finalized the three-team deal sending Kristaps Porzingis to Atlanta.

You can read more about the Holiday/Simons swap in our original report on the deal.

Celtics Notes: Stevens, Horford, Kornet, Mazzulla, Gonzalez, Tatum, Brown

June 26th, 2025 at 10:59am CST by Arthur Hill

Celtics president of basketball operations Brad Stevens had a new first-round pick to discuss in Hugo Gonzalez, but there were more pressing issues to address as he met with the media following Wednesday’s draft, writes Gary Washburn of The Boston Globe. After agreeing to separate trades this week involving Jrue Holiday and Kristaps Porzingis, Stevens talked about their contributions to the franchise and whether any more cost-cutting measures might be on the way.

“The biggest thing is there clearly is a need to prioritize regaining our flexibility,” Stevens said. “Maximizing from an assets standpoint what we can. As far as whatever moves those are a part of, those are all separate, hard, and things that you’re going to have to do your best to make sure you’re in the right position. We knew this was coming. We’ve got to prioritize flexibility.”

Parting with Holiday and Porzingis enabled the Celtics to move below the second apron, freeing them up to aggregate salaries in future trades, send out cash in deals and use trade exceptions. They’re projected to save nearly $200MM in luxury tax penalties, but Stevens emphasized that flexibility rather than frugality was the main motivation for trimming salary.

“Our owners are committed to spending,” Stevens said. “There’s a lot of things that go into these moves and a lot of things that are really important. The second apron basketball penalties are real and I’m not sure I understood how real until they were staring me in the face in the last month. I do think that can’t be overstated.”

There’s more from Boston:

Without a reliable center currently on the roster, Stevens said the team hopes to re-sign free agents Al Horford and Luke Kornet, per Brian Robb of MassLive. Horford made $9.5MM this season while Kornet played for the league minimum and has a chance to get a significant raise on the open market. “I think the biggest thing is, as you look at the rest of the team and what we’re trying to do, there is no question our priorities would be to bring Al and Luke back,” Stevens said. “Those guys are huge parts of this organization,” Stevens said. “They’re going to have, I’m sure, plenty of options all over the place, and that’s well-deserved, but I think that would be a priority. At the same time, I don’t want to put pressure on them. It’s their call ultimately. But, yeah, we would love to have those guys back.”
Stevens revealed that Joe Mazzulla received a contract extension at some point since he was promoted to head coach two years ago, Robb adds in a separate story. “I keep any of those discussions in house,” Stevens said. “But we’ve got Joe under contract for multiple years right now. So, we certainly want Joe to be around here for a long time.”
Regarding Gonzalez, Stevens confirmed the 19-year-old Real Madrid wing won’t be a draft-and-stash project, according to Souichi Terada of MassLive. “Just a big fan of how he plays,” Stevens said. “He’s tough, he’s hard playing, he cuts, he goes after the ball, he competes. He’s got all the intangibles of a winning basketball player. There’s things he can get better at just like everybody else at that age, but competitiveness is at a high level.”
Stevens also provided updates on injured stars Jayson Tatum and Jaylen Brown, relays Kyle Hightower of The Associated Press. Stevens is pleased with Tatum’s progress since undergoing Achilles surgery and emphasized that the team won’t do anything to rush his rehabilitation process. “We won’t put a projected timeline on him for a long, long time,” Stevens said. “… It’s baby steps right now. He’s actually progressed great, but I don’t know what that means in regard to projected timelines. But that will be in consultation with him … and everybody else to make sure when he hits the court he is fully ready, and fully healthy. And that will be the priority.” Brown, who recently had a minimally invasive procedure on his right knee, has already returned to the Celtics’ facility to do some light ball-handling and work around the rim, Stevens adds.

Kings Rumors: Sabonis, PG Targets, Westbrook, Kuminga, LaVine

June 26th, 2025 at 12:14am CST by Luke Adams

The Kings are viewed as “open for business” this offseason and appear willing to discuss a wide variety of potential trade scenarios, according to Sam Amick of The Athletic.

However, while that stance suggests Sacramento wouldn’t immediately shut down inquiries on Domantas Sabonis, team and league sources tell Amick that the club has continued to “signal a commitment” to its star center.

As Amick explains, Sabonis was frustrated by how the De’Aaron Fox situation played out, but he hasn’t asked for a trade and has had positive conversations with new head of basketball operations Scott Perry about the Kings’ plans going forward.

Here’s more on the Kings:

Following up on comments he made during a radio appearance, Amick confirms the Kings had some interest in Jrue Holiday before Boston agreed to send him to Portland, but were concerned about his age and contract. Amick also notes that some of the team’s “power-brokers” were interested in pursuing Hawks guard Trae Young, but the Kings opted against it due to his offense-first style of play and his sizable contract.
Confirming that the Kings have serious interest in Dennis Schröder and are eyeing Tyus Jones, as has been previously reported, Amick says former MVP Russell Westbrook is among the other free agent point guards the front office is considering. Westbrook is on track for unrestricted free agency after declining his player option with Denver.
While Amick classifies it as a long shot, he says the Kings will be among the teams with interest in Warriors restricted free agent forward Jonathan Kuminga this summer. Miami and Chicago have previously been mentioned as possible suitors for Kuminga, who is hoping for an increased role whether he remains in Golden State or ends up elsewhere.
Zach LaVine will become extension-eligible this offseason, but Sacramento has no plans to make a new deal for LaVine a priority, league sources tell Amick. The former Bull has one guaranteed year worth $47.5MM left on his current contract, with a $49MM player option for 2026/27.

Trade Rumors: Brown, White, Holiday, Hawks, NAW, Collins

June 25th, 2025 at 8:06am CST by Luke Adams

After having agreed to trades that send out Jrue Holiday and Kristaps Porzingis, the Celtics have moved below the second tax apron. However, they may not be done dealing yet. Appearing on ESPN’s SportsCenter on Tuesday night (YouTube link), Shams Charania reported that Boston is fielding calls from teams with interest in Jaylen Brown and/or Derrick White.

According to Charania, the Celtics’ preference is still to hang onto Brown and White, and they’ve set “high price thresholds” for both players. But they’re also not entirely shutting down inquiries on those guys, so it remains possible that there will be a team willing to meet Boston’s high asking price.

“At minimum,” Charania says, the Celtics are still a strong candidate to make additional deals involving role players who are a little less valuable than Brown and White. Charania specifically identifies Sam Hauser and Anfernee Simons as players who might fit that bill.

Simons technically isn’t even a Celtic yet, so the agreed-upon deal involving him and Jrue Holiday could be expanded to include more pieces and send Simons to a third team before it’s officially finalized. Even if that trade is completed as currently constructed, Simons could be flipped to another team immediately — his salary simply couldn’t be aggregated with another player’s salary for two months after he’s traded.

Here are a few more trade rumors from around the NBA:

According to Aaron Fentress of The Oregonian (Twitter link), he has heard from two sources who refuted the report claiming that Holiday is unhappy about being traded to the Trail Blazers. We passed along that rumor on Tuesday, but suggested taking it with a grain of salt.
As the Hawks continue to mull various scenarios for how they could use the $25MM+ traded player exception they generated in last summer’s Dejounte Murray deal, one possible target to watch is Nickeil Alexander-Walker, according to Marc Stein and Jake Fischer of The Stein Line (Substack link). The Hawks are expected to show interest in Alexander-Walker, who will be a free agent this summer, and could potentially use that TPE to acquire him via sign-and-trade. The Timberwolves have expressed a desire to retain the three-and-D guard, but will also have Julius Randle‘s and Naz Reid‘s contract situations to resolve.
Although John Collins is considered a potential offseason trade candidate, his market is still taking shape, so a deal seems more likely to happen after the draft than before or during it, per Stein and Fischer. Collins also must exercise his $26.6MM player option before he officially becomes trade-eligible. His decision is due on Thursday.
Heat forward Andrew Wiggins, Raptors forward RJ Barrett and guard Immanuel Quickley, Jazz guards Collin Sexton and Jordan Clarkson, Wizards guard Marcus Smart, and Bucks wing Pat Connaughton are among the other players viewed as candidates to be on the move this summer, according to Stein and Fischer.

Reaction To Jrue Holiday-Anfernee Simons Trade

June 24th, 2025 at 8:08pm CST by Dana Gauruder

The Celtics pulled off a tremendous swap by not only getting off of Jrue Holiday‘s contract but also getting draft capital in return, John Hollinger of The Athletic opines.

Holiday has three years and $104.4MM left on his deal and it was fair to wonder whether the Celtics would have to attach a first-round pick or two to deal him, Hollinger writes. Instead, they’ll receive Anfernee Simons and two second-rounders from the Trail Blazers.

Boston could extend Simons’ deal — he’s got one year left on his contract, Hollinger notes. It’s also quite possible Simons could be flipped for a player with a lower cap hit as Boston looks to continue shedding salary. The Celtics reached an agreement on another cost-cutting deal on Tuesday, dealing Kristaps Porzingis to the Hawks in a three-team deal that will drop them under the second tax apron.

On the flip side, Hollinger believes this is a baffling move for Portland. The Blazers could have spent another year acquiring young talent and developing players. Instead, they’re trading one of their key sources of offense and handing the point guard duties to Scoot Henderson, who has struggled through his first two seasons.

Aaron Fentress of The Oregonian believes top executive Joe Cronin and coach Chauncy Billups are now in a must-win situation with an ownership change looming (Twitter link). The acquisition of Holiday could help the team reach the postseason and his long-term contract is irrelevant to the current regime, Fentress suggests, since Cronin and Billups might not survive an ownership change if the franchise endures another losing campaign.

The Trail Blazers don’t view themselves as a rebuilding team anymore, according to Sean Highkin of The Rose Garden Report (Substack link), who notes that making the postseason was a stated goal when Cronin and Billups received contract extensions after the team won 23 of its last 41 games.

According to Highkin, Holiday is the type of player that Billups has pined for since Damian Lillard was dealt. Holiday is not only a tough, defensive-minded guard but will provide much needed leadership in the locker room.

Highkin also points out that Cronin effectively picked Henderson over Lillard two years ago by drafting him with the No. 3 overall pick and is now choosing Henderson over Simons. Additionally, Highkin believes Holiday will be more willing to come off the bench behind Henderson than Simons would have been during his walk year, though Fentress (Twitter link) expects Holiday to end up in the starting lineup.

Finally, it’s worth noting that Steve Bulpett of Heavy.com has a source who claims Holiday is upset about being sent to Portland.

“If he winds up staying there, I’m sure he’ll be the professional he’s always been and make a positive contribution,” that source told Bulpett. “But he’s not happy with this deal. I’ll be surprised if Portland doesn’t move him on if they can, because right now he does not want to go there. I’m sure if he has to go to Portland, he’ll end up going and it’ll be OK, but right now they want to be somewhere else. But with that contract, it’s not going to be that easy.”

The idea that the Blazers would give up multiple draft picks to acquire Holiday only to try to trade him to another team doesn’t really pass the smell test, nor does it align with the reporting in the past 24 hours. We’ll see if any other reports corroborate the claim that Holiday is unhappy about the deal, but for now, the comments from Bulpett’s source can probably be taken with a grain of salt.

Celtics Trade Porzingis To Hawks In Three-Team Deal

June 24th, 2025 at 6:07pm CST by Dana Gauruder

July 7: The trade is official, according to the Hawks. The final terms are as follows:

Hawks acquire Kristaps Porzingis and a 2026 second-round pick (from Celtics).
Celtics acquire Georges Niang, the Cavaliers’ 2031 second-round pick (from Hawks), and cash (from Nets).
Nets acquire Terance Mann and the draft rights to Drake Powell (No. 22 pick).

“Kristaps is a unique and versatile talent with championship pedigree,” Hawks general manager Onsi Saleh said in a statement. “His ability to stretch the floor, protect the rim, and make plays on both ends adds another dimension to our team. We are fortunate to add a player of his caliber to our group. We’d also like to thank Terence and Georges for their contributions last season and wish them the best.”

June 24: One day after agreeing to trade Jrue Holiday, the Celtics are moving another starter. Kristaps Porzingis is headed to the Hawks in a three-team trade, ESPN’s Shams Charania reports (Twitter link).

Atlanta will acquire Porzingis and a second-round pick in the deal; Terance Mann and Atlanta’s No. 22 pick in Wednesday’s draft are headed to the Nets; and the Celtics are acquiring Georges Niang and a second-round pick.

That second-round pick headed to Boston is coming from Atlanta and is the Cavaliers’ 2031 second-rounder, per Jake Fischer of The Stein Line (Twitter link). In exchange, the Celtics are sending a 2026 second-rounder with “least favorable” language to the Hawks, tweets Michael Scotto of HoopsHype.

The trade, coupled with the agreed-upon Holiday deal with Portland, will allow the Celtics to drop below the second tax apron by $4.5MM, Spotrac contributor Keith Smith tweets. The two deals will reduce their projected luxury tax penalty by nearly $210MM, estimates cap expert Yossi Gozlan (Twitter link).

Porzingis has an expiring $30.7MM contract, while Niang’s expiring deal totals just $8.5MM. Shedding salary has been a goal this offseason for the Celtics, who were facing second-apron restrictions and substantial repeater taxpayer penalties with Jayson Tatum expected to miss most or all of next season while he recovers from a torn Achilles.

A 6’7″ marksman with a career average of 39.9% from beyond the arc, Niang will fit right in as the newest member of the NBA’s leading three-point shooting team in his hometown of Boston. The 32-year-old forward played some of the best basketball of his career after being traded from Cleveland to Atlanta in February, averaging 12.1 points and posting a 41.3% mark on 6.6 threes per game in 28 games for the Hawks.

While the deal gives the Celtics another shooter and creates substantial tax savings, it depletes their depth in the frontcourt, where Al Horford and Luke Kornet are eligible for free agency. Re-signing one or both of those players while potentially adding another big man figures to be a top priority for Boston this summer.

Meanwhile, with Clint Capela headed to free agency, it appears Porzingis will slot in as the Hawks’ starting center ahead of Onyeka Okongwu. He’ll give Atlanta a quality pick-and-pop partner to team up with franchise player Trae Young and will become extension-eligible in July, though it’s unclear whether his new team will look to extend him right away.

Porzingis has an extensive injury history and was hampered this past season by a lingering illness that affected him during the second half and into the postseason, but the expectation is that he’ll be fully recovered by the fall. The veteran big man continues to produce at a high level when he’s available, having averaged 19.5 points, 6.8 rebounds, 2.1 assists, and 1.5 blocks in 28.8 minutes per game across 42 starts for the Celtics in 2024/25, with a shooting line of .483/.412/.809.

The Hawks were rumored to have interest in free agent big man Myles Turner, another rim-protecting, floor-stretching center. Their acquisition of Porzingis will presumably take them out of the mix for Turner, but they’re still well below the projected tax line and continue to explore opportunities to use a trade exception worth $25MM+, either on the trade market or in free agency (via sign-and-trade), tweets Fischer.

Atlanta made “a lot of calls” about Mann this week, according to Fischer (Twitter link), before eventually finding a taker for the 6’5″ swingman.

Mann, a Brooklyn native, has three years and $47MM remaining on his contract. Acquired from the Clippers at this year’s trade deadline, he had a solid finish to the season on Atlanta’s second unit alongside Niang, averaging 9.8 points, 3.1 rebounds, and 2.1 assists in 22.7 minutes per game across 30 outings. He posted a shooting line of .541/.386/.667 as a Hawk.

Accounting for Mann’s $15.5MM salary and the $3.4MM cap hold for the No. 22 overall pick, the Nets will use up roughly $19MM in cap space to make the deal, which can’t be completed until July 6, after the new league year begins and the July moratorium lifts.

Brooklyn still projects to have substantial cap room and now controls an amazing five first-rounders in this week’s draft — Nos. 8, 19, 22, 26, 27 — which figures to lead to more deals.

Luke Adams contributed to this story.

Celtics To Trade Holiday To Blazers For Simons, Second-Round Picks

June 23rd, 2025 at 10:38pm CST by Luke Adams

The Celtics and Trail Blazers have agreed to a trade that will send Jrue Holiday to Portland in exchange for Anfernee Simons and a pair of second-round picks, reports Shams Charania of ESPN (Twitter link).

The second-rounders going to Boston will be the Knicks’ 2030 pick and the Trail Blazers’ own 2031 selection, according to Jake Fischer of The Stein Line (Twitter link).

The move comes less than two years after the teams got together to make a trade sending Holiday from Portland to Boston in October 2023. In that deal, the Blazers – who had just acquired Holiday from the Bucks in the Damian Lillard blockbuster, acquired Malcolm Brogdon, Robert Williams, and two future first-round picks from the Celtics.

Holiday helped the Celtics win a championship in 2024, but had seen his role dialed back significantly since arriving in Boston, having taken a back seat offensively to higher scorers like Jayson Tatum, Jaylen Brown, Derrick White, Kristaps Porzingis, and even Sixth Man of the Year Payton Pritchard.

In 2024/25, Holiday averaged just 11.1 points per game, his lowest mark since his rookie year in 2009/10. He also contributed 4.3 rebounds, 3.9 assists, and 1.1 steals in 30.6 minutes per night, along with a .443/.353/.909 shooting line in 62 outings (all starts).

Given Holiday’s relatively modest role in Boston and a contract that will pay him $32.4MM next season and $104.4MM in total over the next three years, he was considered a strong trade candidate this summer for a Celtics team looking to reduce its payroll.

Boston will do just that in this deal, as Simons is on track to earn approximately $27.7MM in 2025/26, which is the final year of his contract. Although that’s only about $4.7MM less than what Holiday will make, the swap will generate a projected $40MM+ in tax savings for the Celtics, tweets ESPN’s Bobby Marks. Boston is deep in luxury-tax territory and will face more punitive “repeater” taxpayer penalties next season.

The Celtics are still projected to be about $18MM above the second tax apron for ’25/26, per Marks, but they continue to engage in trade discussions involving other players on their roster, sources tell Charania (Twitter link), so more cost-cutting moves are likely coming.

Besides saving some money in the trade, Boston will add a talented 26-year-old guard in Simons, who has averaged 19.9 points and 4.5 assists per game with a .436/.381/.901 shooting line over the past four seasons in Portland since taking on a featured role with the club. Simons should help make up some of the offense the Celtics lost when Tatum went down this spring with an Achilles tear that is expected to sideline him for most or all of next season. Simons will also be eligible to sign a contract extension with the C’s beginning in July.

The Trail Blazers, meanwhile, will bring in a defensive-minded veteran who will help shore up the team’s perimeter defense while serving as a veteran mentor for Scoot Henderson and Shaedon Sharpe, two young guards still on their rookie scale contracts. Holiday turned 35 earlier this month and the back end of his contract could become cumbersome, but Portland presumably believes he can help the team take another step forward after it improved from 21 wins in 2023/24 to 36 victories this past season.

Although Simons was the Blazers’ leading scorer last season, the team had a better net rating when he was off the court (-0.2) than when he was on it (-4.6) and went 8-4 in games he didn’t play.

Assuming the trade doesn’t expand to include additional pieces, the Blazers will become hard-capped at the first tax apron for the 2025/26 league year as a result of taking back more salary than they send out in this deal. The team projects to be roughly $6.6MM below the luxury tax line and $14.7MM below the first apron once the move is finalized, notes Keith Smith of Spotrac (Twitter link).

The Kings, Raptors, and Mavericks were among the other teams who had interest in Holiday, tweets Jared Weiss of The Athletic. They’ll have to look elsewhere for point guard help now, as the Blazers intend to hang onto Holiday in the hopes of making a push for a playoff spot next season, per Fischer (Twitter link).