NBA trade grades 2023-24: Breaking down the Knicks trade for Anunoby

The NBA trade deadline is on the horizon, the market is starting to heat up and a popular name in trade talks has been dealt.

After relative quiet following the blockbuster trade of James Harden from the Philadelphia 76ers to the LA Clippers in late October, there’s been another shake-up in the association after the New York Knicks acquired forward OG Anunoby, center Precious Achiuwa and guard Malachi Flynn from the Toronto Raptors in exchange for guard Immanuel Quickley, forward RJ Barrett and a 2024 second-round pick (via Detroit).

Could the addition of an All-Defensive second-team wing in Anunoby impact the Knicks’ hopes of a deep playoff run this year? What might the Toronto homecoming of Barrett and the hot shooting of Quickley mean for future of the Raptors?

We grade this trade — and all the trades! — below:

LATEST DEALS

Dec. 30: Anunoby to Knicks, Barrett and Quickley to Raptors

New York Knicks get:

F OG Anunoby

C Precious Achiuwa

G Malachi Flynn

Toronto Raptors get:

F RJ Barrett

G Immanuel Quickley

2024 second-round pick (via Detroit)

New York Knicks: A-

This is an interesting trade for many reasons, not least the Knicks playing against their history by prioritizing a role player who’s effective at both ends of the court over bigger names potentially available for trade.

Too often throughout New York’s history of underperforming its market, the Knicks have gone after All-Stars just as they’re about to hit the decline phase of their career, from Bob McAdoo to Amar’e Stoudemire. Having peaked at 17.1 PPG, Anunoby is both not that kind of star and, at age 26, just reaching his NBA peak.

Anunoby gives the Knicks the ace perimeter defender they’ve lacked in the Tom Thibodeau era. An All-Defensive second-team pick a year ago, Anunoby was still probably underrated at that end of the court after leading the league in steals per game. I had him on my first team.

Offensively, New York is giving up a lot of shot creation in this deal. Barrett (27%) and Quickley (24%) were third and fourth on the team in usage, respectively, behind leading scorers Jalen Brunson and Julius Randle. Only once in his career has Anunoby’s usage rate been higher than league average (20%), and it’s down a bit to 18% this season as Toronto has shifted more of its offense to ascending star Scottie Barnes.

In terms of the starting lineup, that’s surely not a bad thing. Barrett has never scored with anything approaching league-average efficiency. This season’s .536 true shooting percentage, a career high, still ranks 52nd of the 57 NBA regulars who have a usage rate of 25% or higher this season. A 34% career 3-point shooter (33% this season), Barrett did little to space the court for Brunson and Randle. Opponents will have to give more respect to Anunoby, who’s at 37.4% this season and 37.5% for his career.

The real question is how this trade affects the Knicks’ strong bench lineups. For the third consecutive year, Quickley has the best on-court net rating among New York full-season regulars, per NBA Advanced Stats. (And, last year, when Quickley was bested by trade deadline pickup Josh Hart, Hart too was part of the Knicks’ second unit.)

To some degree, that says less about Quickley vis-à-vis New York’s starters — particularly Brunson — and more about how the Knicks were able to beat up on weaker opposing benches. To maintain that same success, Thibodeau will probably have to change his approach on staggering the minutes of Brunson and Randle to mix them in with the reserves.

Brunson and Randle have played 986 minutes together, per NBA Advanced Stats, accounting for about 90% of their total playing time this season. For the most part, they’ve played separately only because of foul trouble. With two of New York’s other best shot creators from the second unit promoted to the starting five (Donte DiVincenzo and Isaiah Hartenstein, the latter because of Mitchell Robinson’s injury) and Quickley gone, the Knicks would be wise to keep one of their leading scorers on the court at all times.

It would be a nice bonus if New York got significant contributions from either Achiuwa or Flynn, making them more than throw-ins to this trade. There’s an opportunity for Achiuwa to play at center, with the Knicks losing both Robinson for the long term and backup Jericho Sims (ankle sprain) in the short term. New York is down to Thibodeau-security-blanket Taj Gibson behind Hartenstein. New York could also use Achiuwa as a power forward in bigger lineups that shift Hart to his natural position on the wing.

Flynn was only adequate as Toronto’s backup point guard this season after Fred VanVleet’s departure. A plus shooter in college, he has never hit better than league average from the NBA line, limiting his value as an undersized defender. Similar players have thrived at times in Thibodeau’s pick-and-roll-heavy offense, but the Knicks’ coach may well prefer to use Miles McBride, a better defender, as Quickley’s replacement at point guard.

Just how well Thibodeau can prop up second units without Quickley will determine how much upgrading the starting lineup with Anunoby helps New York this season. A small upgrade could make a big impact. Having gone 5-5 since Robinson’s injury, the Knicks have dropped a half-game back of the Cleveland Cavaliers for the last guaranteed playoff spot in the East.

At the same time, New York is just two games back of the fourth seed and home-court advantage in the first round. Although a deeper playoff run than last year’s loss to the Miami Heat in the conference semifinals appears unlikely, the Knicks have the ability to win a playoff series for a second straight season, something they haven’t done since the year 2000.

The best part of this deal for New York is the way it maintains future flexibility. The Knicks didn’t dip into their stockpile of additional first-round picks, giving up only the Detroit second-round pick (likely to be Nos. 31-33) they nabbed in a draft-night trade down that landed Quentin Grimes as well. Notably, New York didn’t have to give up the contract of Evan Fournier, maintaining the possibility of using him as expiring salary in a trade through next season (if the Knicks exercise their team option).

Given those factors, New York hasn’t exactly punted on adding a star down the road by making this trade. Assuming the Knicks can sign Anunoby to a contract extension — completing this trade Saturday would make him eligible for a four-year deal June 30, the last day extensions are possible, ESPN’s Bobby Marks notes — or re-sign him as an unrestricted free agent, he will likely be more attractive to other teams as the centerpiece of a return than Barrett.

As a result, I think this was a deal New York couldn’t pass on. The Knicks will surely miss Quickley, but his trade value was at its highest leading up to this year’s trade deadline. Having failed to agree to a contract extension before the October deadline for players in the last season of their rookie contracts, Quickley will command a massive raise on his current bargain $4.2 million salary as a restricted free agent next summer.

If they can replace Quickley’s production, it’s possible New York could improve both the rest of the season and in terms of trade flexibility with this deal, which would make it an enormous win.

Toronto Raptors: C

I’d love to give the Raptors’ front office truth serum and see how they rank the two players and pick they received in this deal in terms of importance. For most observers, Barrett will be the key part of what Toronto is getting back.

It’s a homecoming for Barrett, a native of the GTA and the No. 3 pick in 2019 behind All-Stars Zion Williamson and Ja Morant. Though the book is not closed on Barrett’s development at age 23, a similar outcome seems unlikely. Barrett’s scoring average has declined each of the past three seasons, and part of the benefit for the Knicks making this deal now might be moving before his trade value slips.

The expectation when Barrett was drafted was that he would excel at creating his own shot. That’s never proven the case. Based on analysis of shooting data from NBA Advanced Stats, Barrett peaked at a 46% effective field goal percentage last season on shots with more than two seconds of touch time, which typically represent self-created shots. That was still nowhere close to the league average of 50% on these shots.

Over time, Barrett has decreased the rate of his shots that are self-created from 62% in 2021-22, prior to Brunson’s arrival in New York, to 53% this season. But that hasn’t made him any more efficient because, aside from fluky 40% 3-point shooting in 2020-21, Barrett has been below average beyond the arc. It’s possible Barrett can improve in this regard, with fellow Canadian Andrew Wiggins’ development into an All-Star with the Golden State Warriors as a template. With each passing year, however, the odds of Barrett becoming a star decrease.

I think Quickley has the best chance of making this a positive trade for the Raptors. Because he’s exclusively come off the bench after starting 21 games last season, Quickley’s minutes per game are down to 24.0 from the 28.9 he averaged as the runner-up in Sixth Man Award voting in 2022-23. Yet Quickley is scoring the same number of PPG (15.0 vs. 14.9), which means his per-minute scoring is up dramatically to 22.5 per 36 minutes — the same as Barrett, with more playmaking and better efficiency.

The worst true shooting percentage of Quickley’s four-year career (.543) was better than Barrett’s best (.536). He’s up to .598 this season thanks to career-best 39.5% accuracy beyond the arc. That shooting makes Quickley an intriguing fit with Barnes, capable of providing him more floor spacing than current Toronto starting point guard Dennis Schroder. Given how much both are playing, we’ll surely also see some of Schroder and Quickley together in the Raptors’ backcourt.

With Toronto mired out of the play-in at 12-19, moving Anunoby before the deadline was undoubtedly the right decision ahead of his unrestricted free agency. The lingering question is how much the Raptors’ desire to compete now motivated making a deal built primarily on young players rather than picks — or whether pick-heavy offers were no longer available for Anunoby in the last season of his contract.

Although not landing a single first-round pick in this trade is surely a disappointment for Toronto fans dreaming of a draft bounty, the Pistons’ second-rounder has plenty of value in its own right as one of the top picks in the round and possibly No. 31 overall.

It’s possible the Raptors believe they can be more competitive with better depth, and while that’s not unreasonable given Toronto’s point differential (minus-1.3) has been far better than a 12-19 record that’s tied for 11th in the East, that shouldn’t be the goal. Instead, the Raptors would be wise to continue tearing off the bandage by trading All-Star forward Pascal Siakam, also an unrestricted free agent at season’s end.

Given the top-six-protected pick Toronto owes the San Antonio Spurs from the Jakob Poeltl trade, the best course would be losing enough games to have a reasonable chance of keeping their pick. The Raptors would need to have one of the league’s two worst records to assure that outcome, but they would have better than 50-50 odds if they finish in the bottom five.

As a result, trading Anunoby should only be the first step toward Toronto remaking its roster to build around Barnes.

Oct. 31: Harden, Tucker and Petrusev to the LA Clippers for Covington, Batum, Morris, Martin and picks

LA Clippers get:

G James Harden

F P.J. Tucker

F Filip Petrusev

2027 Least favorable first-round pick swap with Oklahoma City or Denver (if 6-30)

Philadelphia 76ers get:

F Robert Covington

F Nicolas Batum

F Marcus Morris

F Kenyon Martin Jr.

2026 first-round pick (the least favorable of OKC, LA Clippers and Houston (if 5-30)

2028 unprotected first-round pick from LA Clippers

2024 second round pick from either Indiana, Toronto, Cleveland or Utah

2029 second round pick from LA Clippers

2029 first-round pick swap via LA Clippers

Oklahoma City Thunder get:

2027 first-round pick swap via Clippers

LA Clippers: B-

So after months of speculation, how does Harden fit with the Clippers? That depends largely on whether — or perhaps more accurately for how long — they get the happy-to-be-here version of Harden we saw take on a pass-first persona when he first arrived in Brooklyn and Philadelphia.

That kind of playmaking is surely something that will help the Clippers, who haven’t had a player average even 6 assists per game over a full season since Paul George and Kawhi Leonard arrived in 2019-20. (Russell Westbrook averaged 7.6 assists in 21 games late last season, and is at 6.7 APG through the first three games this season.) Harden has averaged more than that for a decade running, including a league-high 10.7 last season.

With Harden in the role of lead ball handler, there will be an adjustment for George and Leonard. They combined to possess the ball 51% of the time they were on offense last season, per Second Spectrum tracking on NBA Advanced Stats, with George at 28% and Leonard 23%. That frequency won’t likely be possible with Harden, whose 8.6 minutes time of possession (47% of the time he was on offense) was second highest in the NBA.

In their case, however, the change appears a welcome one they’ve already begun to make. With Westbrook in the starting lineup, their combined possession percentage had dropped to 42% over this season’s first three games, with each at 21%. The results have been positive, with George and Leonard getting the best shots of their Clippers careers, according to Second Spectrum’s quantified shot probability metric, which considers the distance and type of shot as well as the location of nearby defenders.

It’s Harden who will likely be asked to sacrifice the most, at least among the stars. None of the role players the Clippers are trading had a usage rate higher than 18% this season, making it hard to fit in Harden’s 25% usage in last season’s pass-first role — already his lowest since being traded to the Houston Rockets in 2012. Granted, some of that will come from Westbrook, but even Westbrook’s usage had dropped to 17% in the early going playing alongside both George and Leonard.

Perhaps the Clippers hope to resolve the issue by letting Harden and Westbrook lead the offense in games George and Leonard miss while putting them in smaller roles (Westbrook presumably off the bench) when at full strength. That could work, at least for a time. Eventually, Harden has seemed to tire of playmaking, one apparent factor in his decision to seek a trade from the 76ers.

For the Clippers, that shoe dropping may not matter because of their timeline for winning during the late primes of George (33) and Leonard (32). It’s not exactly now or never for the Clippers in the George-Leonard era, but it’s awfully close.

Although the Clippers came up short in a comeback attempt in Utah on Friday, only the Dallas Mavericks have a better offensive rating through three games. And while the Clippers’ top-five defensive rating is due in part to a favorable schedule opening against three teams projected to be in the lottery, they’ve shown enough so far to believe they can legitimately contend in the West so long as George and Leonard are healthy.

I suspect that the fourth quarter against the Jazz was a factor in the Clippers’ decision to push forward with the Harden trade. Down 10 with 9:58 left, they went to a five-out lineup with no traditional center, similar to the one they used to eliminate Utah during the 2021 playoffs without the injured Leonard, reaching the conference finals for the first time in franchise history.

Replace Westbrook with Harden, and the Clippers have the makings of a devastating small-ball unit similar to the ones we saw the Nets deploy in 2021 before dealing with injuries to Harden and Kyrie Irving in their seven-game loss to the Milwaukee Bucks. Tucker, now tethered to Harden with a third different team after playing together with both Philadelphia and the Rockets, also fits into that vision as the undersized 5 the Clippers lacked with the decline in Marcus Morris Sr.’s play.

Tucker’s addition is particularly interesting as the Clippers think about a possible playoff matchup against the Denver Nuggets, who have owned them since pulling off a comeback from a 3-1 deficit in the 2020 bubble conference semifinals. Counting those three wins, the defending champs are 12-2 in their past 14 games against the Clippers, and the past five wins have all come by double digits.

Notably, the 76ers used Tucker to defend Nikola Jokic down the stretch of a win over Denver in January in which Jokic had more turnovers (three) than points (two) in the fourth quarter. Of course, there’s a big difference between defending Jokic with Joel Embiid lurking as a help defender than as the nominal center in small-ball lineups, but Tucker adds a wrinkle to a matchup that has been one-sided of late.

To even worry about beating the Nuggets, the Clippers must first prove they can stay healthy throughout the playoffs. Harden should help relieve the pressure on George and Leonard to stay on the court during the regular season by giving the Clippers another hub for efficient offense in their absence. That, in turn, could help the Clippers be better positioned going into the playoffs after finishing as the fifth seed last season.

The Clippers almost have to contend to justify the cost of this trade, both financial and in terms of precious draft picks. Having finally rebuilt their store of first-rounders depleted by the George trade, the Clippers are now sending out an unprotected first-round pick and swap rights on two others, leaving them in full control of only thier 2030 pick — which is still tradeable.

By taking back Harden and Tucker, the Clippers have added approximately $30 million to their total payroll, including repeater luxury taxes. They can save some money this year by trading Petrusev, whose salary is partially guaranteed for $560,000 according to ESPN’s Bobby Marks, which would also create two open roster spots. Though the Clippers are limited by new restrictions from signing players who are waived while making more than the $12.4 million non-taxpayer midlevel exception this season, that could still allow for useful buyout options.

Down the road, the financial cost will likely be higher as stiffer penalties kick in with the repeater tax and second apron restrictions. The Clippers didn’t give up precious picks to let Harden walk after the season, so they’re replacing four expiring contracts with Tucker (due an $11.5 million player option) and Harden’s new deal. Adding Harden also seems to herald likely extensions for George and Leonard to ensure they’ll stay with the Clippers beyond their player options for 2024-25.

The fascinating counterfactual here is whether the Clippers would have had to give up multiple swaps if they’d simply waited out Philadelphia until the trade deadline. I can understand why the Clippers felt urgency to make a move now. They now get nearly a full season to integrate Harden (and Tucker), while also benefiting from more games of an upgraded roster to boost their seed positioning. I think this was a move worth making — despite the risk.

Philadelphia 76ers: B

As with the Clippers, the Sixers were likely pushed toward making a deal now by the results from the season’s first week — specifically, in their case, the strong start by Eastern Conference Player of the Week Tyrese Maxey. Maxey averaged 30.3 PPG and 6.3 APG as Philadelphia opened 2-1 without Harden, the lone loss coming at Milwaukee against another East contender.

No, Maxey won’t keep shooting 56% from 3-point range, as he has thus far on massive volume (8.3 attempts per game). His ability to shoulder a heavy offensive load (26% usage thus far) still suggested the 76ers offense didn’t need Harden to operate at a high level during the regular season, allowing Daryl Morey to grab value for his disgruntled star now and figure out the rest later.

All along, the reporting has suggested Morey was unwilling to trade Harden unless he got the necessary ammo to deal for another star. By adding two first-round picks, the Sixers now have three tradeable first-rounders — the two acquired in this deal and their own in 2030.

To go with that, Philadelphia has multiple options in terms of expiring salaries. Batum, Covington and Morris are all in the final seasons of their contracts and all in the sweet spot ($11.7 million for Covington, $17.1 million for Morris) where they can be combined after 60 days — still well before the trade deadline — to acquire a highly paid contributor, if not a star. Add in Furkan Korkmaz‘s $5.4 million and the 76ers have $45 million worth of expiring salaries not in their rotation to date.

If Philadelphia can’t find a deal, this trade very much preserves the option of opening up cap room next summer. None of the four players the Sixers added are under contract for 2024-25, while Philadelphia shed Tucker’s possible player option, leaving Embiid for the moment as the only fully guaranteed salary for next season on Philadelphia’s roster. (Paul Reed‘s $7.7 million salary guarantees if the 76ers reach the conference semifinals, per the terms of a toxic offer sheet from the Utah Jazz, while Philadelphia must decide Tuesday on Jaden Springer‘s $4 million team option for 2024-25.)

It’s even possible the Sixers could have their cake and eat it too by using some of the draft compensation they acquired to deal for another player on an expiring contract, like Buddy Hield of the Indiana Pacers, who could help this season with the possibility of re-signing using Bird rights as a backup plan next summer.

To that end, Philadelphia won on the margins not only by shedding Tucker but also by landing Martin, whose minimum salary will give him a minuscule cap hold as an unrestricted free agent next summer. The Sixers could retain the rights to Martin, Maxey and De’Anthony Melton with a combined $30 million in cap holds, far less than what they will surely command on the open market.

In the here and now, it will be interesting to see whether Philly can get away with playing Martin as a backup 4 alongside Reed in lineups that are long on athleticism but short on shooting. That’s one option for filling the minutes Tucker was playing in the Sixers’ rotation. Batum is perhaps the strongest candidate to replace Tucker, while Covington — returning to where he started his career as Embiid’s teammate during the Process era — is also an option.

As compared to the team the 76ers have put on the court this season, they’re undoubtedly deeper after this trade. They’re also far more dependent on the duo of Embiid and Maxey for shot creation, and an injury to either of their stars could accelerate Philadelphia’s timetable for making a deal using expiring contracts and the newly added picks.

Certainly, the best version of the 2023-24 Sixers involved Harden putting aside his differences with Morey and playing normally the rest of the season. It’s impossible from the outside to say exactly how realistic that option was. If Philadelphia didn’t believe that outcome was realistic, this version of the trade at least seems to spin Harden’s value forward in a way that could help rebuild a championship contender around Embiid. (Harden’s salary was $176.7 million, and combined with a tax bill of $19.8 million was costing the team $196.5 million total.)

Oklahoma City Thunder: A-

The value of adding a third team to this deal is more apparent now that we see its full structure. The Sixers don’t own their 2027 first-round pick outright to swap with the Clippers, as they’ll potentially either send it to the Thunder themselves (who else?) or as a top-8 protected pick to the Brooklyn Nets from the deal to add Harden.

By contrast, Oklahoma City may be able to benefit from swapping the weakest of their potential 2027 first-round picks — including the one from Philadelphia, if it hasn’t conveyed already, and another protected one from the Nuggets — for the Clippers’ pick.

It’s likely the worst of those picks will be the Thunder’s own. A lot can happen between now and then, but Oklahoma City probably has the league’s most favorable outlook for that season, which will see Shai Gilgeous-Alexander in the thick of his prime at age 28. The Thunder’s other young talented players project to just be peaking then, with Jalen Williams age 26 and Chet Holmgren and Josh Giddey playing the season at age 24.

Already, Oklahoma City ranked third in ESPN’s Future Power Rankings, which cover the three seasons prior to 2026-27, based on on a talented young core and stockpile of draft picks. That stockpile also means the 2026 first-round pick the Thunder are giving up is unlikely to be in the lottery. Derek Bodner of PHLY Sports reported it will be the worst of multiple picks Oklahoma City owns that season, including one from the Clippers dating back to the George trade.

Based on those stipulations and the number of picks the Thunder already have, converting a full first-rounder into a swap makes sense in terms of maximizing the potential upside for Oklahoma City even if the average expected value of a swap is not as good as having a first-round pick outright.

Oct. 1: Holiday to Boston for Brogdon, Williams and picks

Boston Celtics get:

G Jrue Holiday

Portland Trail Blazers get:

G Malcolm Brogdon

C Robert Williams III

2024 first-round pick (Golden State)

2029 unprotected first-round pick

Boston: B+

Buckle up. The Eastern Conference title race got dramatically more interesting in the past four days, with the Celtics responding to the Milwaukee Bucks adding Damian Lillard by nabbing the All-Star they sent the Blazers in return, Holiday.

Holiday is an ideal fit alongside Boston’s core players, supplying the organizing ability the Celtics hoped they would get when they added Brogdon last summer without compromising either their outside shooting or their defense. Holiday is an upgrade offensively over Marcus Smart — sent by Boston to the Memphis Grizzlies earlier this offseason in a deal that netted one of the first-round picks sent to Portland in this trade — and little, if any, defensive downgrade from the 2021-22 Defensive Player of the Year.

With Holiday, the Celtics could have the NBA’s best six-player core. Coach Joe Mazzulla can still toggle back and forth between smaller lineups with Holiday and Derrick White together in the backcourt and Jaylen Brown and Jayson Tatum at forward and bigger units that put both Al Horford and newcomer Kristaps Porzingis in the frontcourt together, shifting Brown and Tatum to the wing at the likely expense of White.

The smaller group in particular gives opposing offenses no place to attack, a hallmark of the defense that has helped Boston to the Eastern Conference finals three of the last four years. The hope, too, is the Celtics upgrading their shooting with Holiday — at least based on the regular season, when he’s hit 39.5% of his 3s during three seasons with the Bucks before fading to 30% in the playoffs over that span — and Porzingis can get them over the top offensively to win a title.

Just how much Holiday minimizes offensive miscues will also be key. He’s averaged more turnovers than Smart, including 2.9 per game last season, (Smart was at 2.3 in similar playing time) but that was with more ball handling responsibility. Holiday held the ball for 6.1 minutes per game last season, according to Second Spectrum tracking on NBA Advanced Stats, far more than Smart (4.1 MPG, second on Boston behind Tatum).

Beyond those top six, however, the Celtics’ depth now looks shaky after they gave up two rotation players for Holiday. They return just one other player who saw more than 60 minutes of action in last year’s playoffs, forward Sam Hauser. The in-house options to fill out the rotation are holdover Payton Pritchard and newcomers Oshae Brissett and Svi Mykhailiuk. And center depth goes from a strength with Horford, Porzingis and Williams to a weakness. Horford sat out at least one game of back-to-back sets last season, leaving Luke Kornet as the only other center on a full NBA contract besides Porzingis for those games.

It will be interesting to see if Boston can add another reliable contributor via trade. The extra pick acquired in the Smart trade allowed the Celtics to complete this deal without dipping into their own tradeable first-round picks in 2024 and 2026 (or, if preferred, 2025 and 2027). The challenge will be finding matching salary with only Pritchard (making $4 million in the last season of his rookie deal) at more than the minimum outside the core.

The Celtics could also fill the roster spot created in this trade with a free agent, but will be subject to new restrictions preventing teams above the first luxury-tax apron from signing players waived midseason who previously were making more than the value of the non-taxpayer midlevel exception ($12.4 million).

(Notably, those restrictions don’t apply to Reggie Bullock after the veteran wing agreed to a buyout with the San Antonio Spurs on Saturday. Bullock doesn’t qualify because the move will come before the start of the regular season, and also because his salary was below that threshold. The battle to sign Bullock could be an interesting pivot point in the title race, with both Boston and Milwaukee surely in the mix.)

At the highest-leverage moments, that hit to the Celtics’ depth might not matter if the team is healthy and the bulk of minutes are going to the top six players. Boston, much like Milwaukee and the Phoenix Suns in the Western Conference, is betting on top-end talent over depth. Like those teams, the Celtics are also spending heavily in pursuit of a title right now.

Assuming Boston keeps an extra player on the roster to fill the spot vacated in this trade, the team’s luxury-tax bill will jump nearly $15 million based on the likely incentives in Holiday’s contract. (Holiday has $1.9 million in incentives counted as likely, per ESPN’s Bobby Marks, based on being an All-Star, making an All-Defensive team and other statistical thresholds.)

That’s just this season. Holiday is heading into the final season of his contract and will be eligible to add up to four years and $200-plus million in an extension starting six months after this deal is complete. Sources told ESPN’s Adrian Wojnarowski the Celtics are eager to retain him long-term, which makes sense. Boston gave up too much for Holiday to simply be a rental.

Wherever the two sides land on an extension, Holiday is likely looking at a raise next season at the same time Brown’s supermax extension kicks in, which could push Boston’s payroll into the stratosphere. For now, the Celtics having the core of a championship contender under contract through 2024-25 is a positive. At some point, though, the cost of keeping this group together with a looming supermax for Tatum will become prohibitive.

Between now and that unknown date, Boston is hoping to add an 18th championship banner. With the addition of Holiday, I again see the Celtics as the favorites to win the East — and perhaps even the title. This is the downside of how the Bucks pursued the Lillard deal. By sending Holiday to the Blazers, Milwaukee gave up any control over where he was rerouted that may have been possible if the trades were negotiated simultaneously. The Bucks surely hoped Holiday would end up in the Western Conference. Instead, he’s headed to their biggest rival on paper in the East.

The rematch of the thrilling, seven-game Boston-Milwaukee series we saw in the 2022 conference semifinals never materialized last spring because the Bucks were upset in the first round by the Miami Heat, who eventually took down the Celtics in the conference finals. If we get Boston-Milwaukee round two, the drama, now, will be greater than ever.

Portland: A-

Splitting the Lillard trade in two — at a minimum — seems to have paid off for the Blazers, who were able to get three combined first-round picks and two swaps for their star without taking back any bad salary in return.

There still might be another trade for Portland to make involving Brogdon, who will surely have value to contending teams. Making $22.5 million this season and next, Brogdon is an easy salary fit and, like Lillard and Holiday before him, he doesn’t match up with the Blazers’ timeline at age 30.

It’s possible Portland could move Brogdon again quickly, though in a scenario where he’s retained as a veteran mentor for the Blazers’ young guards (including Anfernee Simons and recent lottery picks Scoot Henderson and Shaedon Sharpe), there’s less worry about his trade value decreasing between now and the deadline.

Wojnarowski reported Portland intends to keep Williams, who turns 26 later this month, meaning the center position has gone from a major weakness for the Blazers to a surprising strength. In Williams and Deandre Ayton, Portland now has two starting-caliber centers in their athletic prime. The challenge for coach Chauncey Billups may be finding enough minutes to keep both happy, and it will be intriguing to see whether the Blazers try playing both together at times.

The hot take here is that Williams, who has never averaged more than 10 points per game in a season and spent most of the 2023 playoffs coming off the bench, might be the better of Portland’s two centers. Although Williams isn’t nearly as skilled offensively as Ayton, he does a better job of playing to his strengths as a career 73% shooter who is one of the league’s best defenders when healthy.

Williams also brings a favorable contract paying him less than the non-taxpayer midlevel exception over the next three years. So long as he can stay healthy, Williams is a great pickup for the Blazers.

Still, the real carrot of this deal for Portland is diversifying the team’s portfolio of draft picks. The three extra first-rounders the Blazers have added in their pair of deals come from three different teams, giving Portland multiple shots at landing a lottery pick. That’s least likely with the Golden State pick this upcoming season, though the Warriors are no playoff locks in a loaded West.

Intriguingly, both the unprotected Celtics and Bucks picks the Blazers added are in 2029. I’d imagine Portland initially preferred getting a 2030 pick from Boston, going as far out as possible, but the Celtics’ roster could look very different by 2029. The upside isn’t as evident as with Milwaukee’s 2029 pick, but it’s plausible both teams could have cycled out of being contenders by then, giving Portland two bites at the apple just as its current core should be beginning to peak.

For now, it seems like the Blazers read the Lillard market correctly, using Holiday as an intermediary to get the kind of draft value they wanted while also adding a pair of talented centers to their roster. And although a possible Brogdon trade still looms, his presence doesn’t figure to hang over media day and training camp such as having Lillard or Holiday on the roster would have.

Sept. 27: Lillard to Milwaukee in three-team trade

Milwaukee Bucks get:

G Damian Lillard

Phoenix Suns get:

SG Grayson Allen

SG Keon Johnson

SF Nassir Little

C Jusuf Nurkic

Portland Trail Blazers get:

C Deandre Ayton

F Toumani Camara

PG Jrue Holiday

2028 unprotected swap rights

2029 unprotected first-round pick

2030 unprotected swap rights

Milwaukee: B+

Whoa. The Bucks were never seen as a possible Lillard destination — they weren’t among the four teams we highlighted in a recent piece on potential landing spots. Yet they fit the most important criterion for a deal to make sense: the ability to win a title during the remainder of Lillard’s late prime years.

The urgency to win now ratcheted up lately with Milwaukee star Giannis Antetokounmpo telling The New York Times, then subsequently reiterating, that he would sign an extension with the Bucks only if he believed “everybody’s going for a championship.”

Given Antetokounmpo could reach unrestricted free agency in the summer of 2025 by declining a player option for the 2025-26 season, that gave Milwaukee a two-year window to add to the 2021 title and persuade Giannis to stick around. Over the years, we’ve seen a variety of responses to stars nearing free agency. The Cleveland Cavaliers added a variety of veterans in an effort to win a championship before LeBron James became a free agent in the summer of 2010, then adjusted during LeBron’s second stint in Cleveland to prioritize building for a post-James future by making a lottery pick from the Brooklyn Nets the centerpiece of the trade sending Kyrie Irving to the Boston Celtics.

I’m not sure we’ve ever seen a team go all-in quite like this to retain a star. The Bucks no longer control any of their future first-round picks within the seven-year window teams have access to them, having now traded a third unprotected pick to go along with swap rights in the other four years. If Giannis walks in free agency, Milwaukee will be staring at a rebuild without the protective netting of the lottery. Trading Lillard a year or two down the road likely won’t yield nearly this kind of return.

For now, however, Lillard is the best player the Bucks could realistically have paired with Antetokounmpo. Giannis has never played with a pick-and-roll ball handler anything like Lillard, still arguably the league’s most dangerous player with the ball. Per Second Spectrum tracking, Lillard pick-and-rolls yielded 1.16 points per play last season when either he or the player he passed to shot, was fouled or turned the ball over, second only to Luka Doncic among players who ran at least 500 pick-and-rolls.

That performance came with a below-average group of big men screening for Lillard. According to Second Spectrum data, backup center Drew Eubanks was his most common pick-and-roll partner. Replace Eubanks with Giannis and put shooters around them at all three positions and Milwaukee’s pick-and-roll game should be lethal.

There will be an adjustment for Antetokounmpo to a style centered on pick-and-rolls. He was the ball handler in pick-and-rolls almost as regularly (627 times, per Second Spectrum numbers) as the screener (859) last season.

Between Holiday and predecessor Eric Bledsoe, the Bucks have long prioritized defense over playmaking in their point guards. Last season’s 59.7 on-ball picks per game, the NBA’s fourth-lowest mark, was their highest average at any point in Mike Budenholzer‘s five years as head coach in Milwaukee. Lillard alone ran 36.4 per game, seventh-most, according to Second Spectrum.

Surely, Lillard will need to adjust as well to playing with another star. He hasn’t played with an All-Star since he and LaMarcus Aldridge were teammates with the Blazers for three seasons until Aldridge left for the San Antonio Spurs in the summer of 2015. Now Lillard joins Giannis and Khris Middleton, an All-Star in 2022 before suffering an injury-marred 2022-23 campaign. Lillard’s shooting ability makes him threatening without the ball, but multiple coaches in Portland were unable to get the kind of dynamic off-ball movement from Lillard that sets Stephen Curry apart from other point guards who can shoot.

No matter the adjustment, this version of the Bucks has too much talent and too much shooting — even with the loss of Allen, whose minutes will likely go to new sharpshooter Malik Beasley — not to be an elite offense after finishing a league-average 15th in points per possession last season. Milwaukee’s championship ceiling will be determined on defense.

Losing Holiday substantially weakens the Bucks’ perimeter defense. They relied on him to handle opponents’ most challenging guard or wing, assignments that could now go to Pat Connaughton in the starting five. Jae Crowder is another option against bigger wings, while Milwaukee is surely hoping 2022 first-round pick MarJon Beauchamp will grow into that role sooner than later, which would require improvement as a shooter. (Expect the Bucks to tout keeping Beauchamp out of this deal as a key to making it.)

None of those options is on the level of Holiday, and the Bucks will have to find ways to stash Lillard on nonthreatening opponent perimeter players in a way that wasn’t necessary for any starters on the championship team. Milwaukee is gambling that the offensive upgrade with Lillard will outweigh the defensive drop-off.

Before we see how things play out on the court, I’m inclined to agree. In a conference where there’s uncertainty about every contender, adding Lillard is enough to make the Bucks my pick. As a bonus, they’ve also weakened the Miami Heat‘s title chances by not getting Lillard.

Like so many all-in trades we’ve seen in recent years in pursuit of a championship, whether Milwaukee adds a second title with Giannis will probably determine whether this trade is a success. If not, the Bucks could rue giving up what might be a lottery pick and potentially swapping down two other times. If so, the memories of a championship won with a guard-big duo along the lines of the Oscar Robertson-Kareem Abdul-Jabbar pairing that brought the franchise’s first in 1971 would warm Milwaukee fans’ hearts through a number of long winters.

Phoenix: B-

The undercard of the Lillard trade is interesting in its own right. The Suns are also all-in on winning a championship after adding Bradley Beal this past summer and have chosen to flip Ayton into multiple potential contributors to that effort. The most important player of this deal is Nurkic, the direct replacement for Ayton at center. It appears Phoenix views Nurkic as the kind of defensive-minded role player it’s had success with in place of Ayton, and that’s not really Nurkic’s game at this stage of his career.

Playing a conservative drop coverage under Terry Stotts in Portland, Nurkic was a strong rim protector before a compound leg fracture in March 2019 sidelined him for nearly a year. During 2017-18 and 2018-19, when the Blazers were average or better defensively, Nurkic limited opponents to sub-55% shooting on attempts within 5 feet, according to Second Spectrum tracking on NBA Advanced Stats. That ballooned to 68% in 2021-22, worst among players who defended at least four such attempts per game, before improving to 58% last season.

Portland remained one of the league’s worst defensive teams (28th in defensive rating) and was better with Eubanks in the middle. (One amusing part of this trade is Nurkic being reunited with his backup last season, who signed with the Suns as a free agent this past summer and may continue finishing games in place of Nurkic.)

Offensively, Nurkic is more of a volume scorer than the kind of efficient role player you’d want next to Phoenix’s perimeter stars. His 57% 2-point shooting sounds good until you realize the average center made 62% of his shots inside the arc. Nurkic did add a 3-point element last season, hitting a career-high 43 triples at a 36% clip, but it will be interesting to see how he handles being the fifth option for the Suns on offense. Nurkic has had a usage rate of 22% or higher every season since his rookie campaign.

To me, the better addition for Phoenix from the Blazers is Little, who has a chance to emerge as a starter. Still just 22, Little shot a career-best 37% from 3-point range last season and has the skills to serve as the Suns’ primary perimeter defender. Little never seemed to fully win over Portland coach Chauncey Billups, however, averaging just 18.1 MPG off the bench. If Little continues to develop, the four-year rookie extension he’s starting worth $28 million could be an enormous bargain.

In Allen, Phoenix has added a shooter with defensive limitations. Allen was taken five picks ahead of former Suns guard Landry Shamet in the 2018 draft, and the two players have always been tied together, signing extensions worth similar amounts two years ago. After dealing Shamet as part of the return for Beal, Phoenix has replaced him with Allen, and I think that’s an upgrade. Allen, who started all five playoff games for Milwaukee last year, has shown more ability to stay on the court defensively in the preseason.

Amusingly, the Suns could try to make the reverse version of this trade at the deadline, combining multiple salaries for one player making more. That timeline is important because starting next season, restrictions will prevent teams above the second luxury-tax apron from aggregating salaries together in trade. (As my colleague Bobby Marks noted, the Bucks would not have been able to deal for Lillard using Holiday and Allen if that rule were in place.) By midseason, Phoenix will have more information about which role players fit and which are extraneous.

Between now and then, the Suns will surely try to find a taker for Keon Johnson, who’s at risk of being cut otherwise. Phoenix has 15 guaranteed contracts and would like to keep Jordan Goodwin, whose salary is partially guaranteed. Assuming the Suns waive at least one of their players who aren’t fully guaranteed deals (Ish Wainright is nonguaranteed), this deal saves Phoenix a modest amount in luxury taxes. Moving Johnson would produce far more savings, although the Suns have only second-round picks available to incentivize a team with cap space or a trade exception to take him.

I’d have liked this deal a bit more for Phoenix immediately after the Beal trade before it became clear how much depth the Suns would add in free agency with only minimum-salary contracts to offer. Allen may not prove an upgrade on Gordon or Little or Keita Bates-Diop, although the more options for Phoenix, the better.

Portland: B+

All along, I’ve felt that trading Lillard before training camp was the right move for the Blazers. It’s easy to talk about waiting for the best possible deal in July, with little pressure to make a move. Urgency clearly set in for Portland as Monday’s media day and the start of training camp approached.

With one caveat, the Blazers can look to a future built around recent lottery picks Scoot Henderson and Shaedon Sharpe. They’ve also locked in Lillard’s trade value without having to risk the possibility of an injury or age-related decline making it more difficult to deal him than it is coming off an All-NBA season.

The key caveat, of course, is that Portland has swapped one 33-year-old All-Star point guard for another. Holiday isn’t the kind of young talent a star trade would typically return, and without any ties to the Blazers or the kind of drawing power as Lillard, it seems inevitable Holiday will be traded again soon. Just how much Portland gets in return will determine how this deal compares to the possibility of sending Lillard to his desired destination, the Miami Heat.

From this trade alone, the Blazers aren’t returning nearly as much volume in terms of draft picks as Miami could have offered. Portland got a single first-round pick outright, though it’s a potentially great one. Even if Giannis extends his contract, he’ll be 34 by 2029. Lillard will be 38. The odds Milwaukee is still a contender by that point are remote, and there’s a reasonable chance of the Bucks bottoming out without either star (or, as noted, their own picks in between now and then).

The young talent the Blazers did add comes with baggage. The Suns’ willingness to part with Ayton, 25, without getting any above-average starters or any draft picks showcases just how eager Phoenix was to move on from the 2018 No. 1 pick. Ayton gets a fresh start in Portland at a position where the Blazers had no promising player on the timeline of the rest of their young core.

If Portland can get the kind of performance we saw from Ayton in the 2021 playoffs, when he averaged 15.8 points per game and 11.8 rebounds per game while helping the Suns to the NBA Finals, getting his contract at this low cost is a bargain. Admittedly, I’m skeptical that such a transformation is coming, but in the worst-case scenario, Ayton’s current deal expires in time for the Blazers to have massive salary-cap space in the summer of 2026, when Henderson will be entering the final year of his rookie contract.

Camara, the No. 52 overall pick in this year’s draft out of Dayton, is by far the lowest-profile part of this deal, but Portland likely also values him. Camara played well for Phoenix at summer league in Las Vegas, averaging 16.3 PPG and 7.0 RPG in four games. Camara has a better chance of playing time with the Blazers than if he had stayed with the Suns.

Above and beyond the potential to reroute Holiday, Portland still feels like a team in transition. The Blazers re-signed Jerami Grant to a five-year, $160 million deal this summer, and the 29-year-old forward feels out of place on a team that’s rebuilding. Adding Ayton makes it unlikely Portland will bottom out, but this trade now puts a timeline on the Blazers contending. Ideally, they want to be contenders again by 2028, maximizing the potential value of pick swaps then and in 2030, when Henderson (24 in 2028) and Sharpe (25) will be hitting their prime years.

As a result, more change is sure to come in Portland. The Blazers can continue the process with clarity now that they’ve secured value in a Lillard trade that seems to have left all sides satisfied.

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