As NBA free agency waned and the league settled into an offseason of vacations, workouts and the FIBA World Cup, Damian Lillard’s standoff with the Portland Trail Blazers remained unresolved.
While Blazers general manager Joe Cronin said Lillard’s July trade request could drag into the 2023-24 season, he also didn’t want training camp to start with trouble and an unhappy Lillard, one of the franchise’s all-time greats and a fan favorite.
Meanwhile, Milwaukee and Boston knew the status quo wasn’t good enough. Miami eliminated both in last season's playoffs, beating the Bucks in the first round and the Celtics in the Eastern Conference finals, a major disappointment for the Bucks who won the title in 2021 and the Celtics who lost to Golden State in the 2022 Finals.
Phoenix and new owner Mat Ishbia put together a team featuring Devin Booker, Kevin Durant and Bradley Beal, but in acquiring Durant at last season’s trade deadline and Beal in the offseason, the Suns lost depth.
About two weeks before training camps opened, the Bucks and Blazers quietly rekindled a Lillard trade discussion.
As players settled in their home markets for the start of training camps, the Bucks, Celtics, Suns and Blazers executed two trades that reshaped the NBA landscape and altered the projected hierarchy in the East. In the span of four days last week, Lillard ended up with Milwaukee, Jrue Holiday went from Milwaukee to Portland to Boston, and on paper, Boston and Milwaukee emerged as favorites to meet in the East finals.
Here’s how the trades impacted teams and the league for 2023-24 and beyond:
Expectations were already high for a team that won 58 games and was the league’s top seed last season, but the arrival of Lillard, 33, brings a dynamism to the organization.
The Bucks were title contenders as formerly constructed, with Holiday and Brook Lopez arguably coming off their best seasons and Giannis Antetokounmpo and Khris Middleton healthy after summer knee surgeries. But there was a "wait until April" feeling about it all. Even with new head coach Adrian Griffin in place, it wasn’t an uncommon sentiment to think this championship-experienced team would figure out a way to a top-three seed − and that’s when the real season starts.
But Lillard’s presence turned that all on its head. Not only is a top 75 player of all-time joining the team but one who is a rare individual scorer (career-high 32.2 points per game last season) at the level of Antetokounmpo. A player who will get MVP votes, not just All-Star tallies. And a player with four years and $216.2 million remaining on his contract.
"It's unique and hopefully very impactful," general manager Jon Horst said. "You can’t get something without giving up something in this league, and we all know and understand the quality of person and player that Jrue Holiday is and what his family have meant to this community. We’ll forever be grateful for that.
"In the same breath, we’re really excited about this team and the changes that‘s happening, the way that we’re going to play and the dominance that hopefully we play with."
The regular season still may feel like a formality for the Bucks, but the recent history of such stars coming together − Kyrie Irving, Kevin Durant and James Harden in Brooklyn; Harden and Joel Embiid in Philadelphia; Durant and Devin Booker in Phoenix; Irving and and Luka Doncic in Dallas − shows a need for patience.
Of course, the end goal is having it all together for a playoff run that will go beyond the second round, which is something that has not happened the past two years. Whatever the reasons for those exits, they preceded a coaching change, Antetokounmpo’s summer concerns about the organization’s commitment to winning, and the trade for Lillard. Toss in an April ownership change from Marc Lasry to the Haslam Sports Group, and this has been a massive offseason for one of the best, most consistent teams the past five seasons.
Holiday’s eventual arrival in Boston (via Portland) impacts the Bucks directly, too. While the Bucks and Celtics play four times in the regular season, they were the top two seeds in the playoffs last year and have played each other in the postseason three times since 2016-17. Another playoff meeting feels like it’s on the horizon, and if Lillard was acquired to boost the Bucks’ playoff offense, Holiday is in Celtic green to prevent that.
Since winning the 2020-21 championship, the Bucks have remained a true title contender that had disappointing, descending playoff finishes. The expectations haven’t changed with Lillard in Milwaukee. But the hope is the results will, which is another step toward securing Antetokounmpo's future with the Bucks.
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The Suns and Blazers had been in conversations about Deandre Ayton, but those talks really picked up 48 hours before the deal went down Sept. 27.
The Bucks and Blazers had worked out a deal regarding Lillard. They still needed a third team.
The key for Phoenix is Ishbia, who has been highly aggressive in making major moves starting with the Durant trade and continuing with the Beal move that sent Chris Paul to Washington.
Getting Jusuf Nurkic addresses moving Ayton to Portland. The 7-footer isn’t as talented, doesn’t have the upside, but his passing ability makes him perhaps a better fit playing off Booker, Durant and Beal.
Nurkic has dealt with injuries in recent years. That should be a concern moving forward. However, the Suns and Ayton needed to part ways because the relationship wasn’t the best. Financially, the move will help the Suns start working their way under the second tax apron, a situation that limits roster flexibility.
Grayson Allen is the wild card. Coming from Milwaukee, Allen is a career 39.5% 3-point shooter.
The Suns have added more shooting through offseason moves, but Allen has a chance to show he can do more to earn meaningful minutes for a team with championship aspirations.
Ishbia has been a willing spender as evidenced in buying the Suns and WNBA’s Phoenix Mercury on a $4 billion valuation.
Booker’s supermax deal of four years, $224 million kicks in next season. Durant is in the second year of a four-year, $194 million deal, and Beal is in the second year of a five-year, $251 million deal with a player option on the final year.
The Suns are paying top dollar and want high-end results under coach Frank Vogel, who replaced Monty Williams.
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Boston wants its 18th championship, which would break a tie with the Los Angeles Lakers for most in NBA history and give the franchise its first title since 2008.
With Jayson Tatum and Jaylen Brown, the Celtics have the superstar tandem to get it done, and the addition of Kristaps Porzingis and Holiday makes them a force.
"As a competitor, he’s an assassin," Brown said of Holiday.
When the Celtics lost Marcus Smart to Memphis in the three-team deal with Washington for Porzingis, president of basketball operations Brad Stevens knew he needed more talent. Though he doesn’t have quite the same reputation as his predecessor, Danny Ainge, in fleecing teams, Stevens has acquired Derrick White, Porzingis and now Holiday, 33, in trades.
Part of Milwaukee's 2021 championship team, Holiday, who has two seasons left on his contract, is coming off one of the best seasons of his 14-year career. He averaged 19.3 points and a team-high 7.4 assists and also had a career- high 5.1 rebounds per game and was a first-team All-Defense selection. Guard Derrick White was second-team All-Defense last season, giving the Celtics an outstanding defensive backcourt.
"There’s a list of guys in the league that you always think you’d never have a real chance to get that you think are like perfect fits, that you’d love to be a Celtic, and Jrue is one of those guys," Stevens said. "The reasons are, everybody can see what he does on the court, and he’s a really good player. Four-time All-Star. His defense has been well documented, etcetera.
"He's an elite teammate, (has) elite competitive character, all of those things."
The price was high. The Celtics sent Malcolm Brogdon, Robert Williams and two first-round picks to Portland. The Celtics’ top six players might be the best top six in the league, but they lack depth, which is important in a deep playoff run.
How that bench grows will help determine how close that 18th title is.
Cronin, the GM, was in a difficult spot. One of the franchise’s all-time greats wanted out, and initially at least, Lillard wanted to play for only one team, the Heat. Cronin sought the best deal for the Blazers, which didn’t grant Lillard’s wish. That created tension and frustration.
But Cronin didn’t cave to external pressure from any camp. In the trades, the Blazers acquired Robert Williams, Malcolm Brogdon, Ayton, Toumani Camara, three first-round picks (one in 2024, two in 2029) and the right to swap first-round picks with Milwaukee in 2028 and 2030. Brogdon, and other veterans, including Jerami Grant, could be traded, too.
This is a massive rebuild for the front office and third-year coach Chauncey Billups. It is focused on Anfernee Simons, 24, Scoot Henderson, the No. 2 pick in the June draft, rookie Kris Murray, the No. 23 pick, and Shaedon Sharpe, 20. Ayton and Williams are just 25.
"Finally, Chauncey has a group capable of playing the style that he wants to play," Cronin said. "Now, he'll be able to implement all of this. We've got some talented guards who will need his leadership, will need his mentoring, need his voice, need to be challenged by him. Chauncey's got such a good demeanor and the players think so highly of him. He'll give them a hug and then challenge them."
But it will require years to determine how successful Cronin's moves will be. The Blazers haven't reached the Finals since 1992 and last won a title in 1977.
Heat mentality is such that star guard Jimmy Butler said at media day Monday, "This is our year. This is the one. And this one's going to feel real good by the way."
But for a team that lost to Denver in the 2023 Finals and sought to improve ahead of this season, the Heat came up short, losing Gabe Vincent and Max Strus in free agency and failing to reach a deal with Portland – first for Lillard and then for Holiday.
Yes, the Heat will say they have enough because that’s what they do. And they will field a competitive roster with Butler, Bam Adebayo, Tyler Herro, Kyle Lowry, Kevin Love and others.
However, it must sting the Heat that they were unable to make a significant move. Even though they won the East last season, they are not the two favorites to win the conference.
The 76ers opened training camp without guard James Harden, who wants a trade. But the Sixers have been unable to accommodate, and like the Heat, they did not have the kind of offseason that puts them on the same plane as Milwaukee and Boston – even with 2022-23 MVP Joel Embiid.
This is an unpleasant situation with the potential to turn uglier. Harden has already called Sixers president of basketball operations Daryl Morey a liar, and the NBA fined Harden for indicating he won’t honor his contract unless traded. Philadelphia wants to frame itself as a contender, but amid this chaos, it might be the third-best team in its division behind Boston and New York.
Until Harden is traded and the Sixers get value in return, it's difficult to envision Philadelphia as one of the elite teams in the league.
Follow Jeff Zillgitt on social media @JeffZillgitt, Jim Owczarski @JimOwczarski and Duane Rankin @DuaneRankin
