Wednesday’s history-altering hurricane that sent Damian Lillard to the Milwaukee Bucks, Deandre Ayton and Jrue Holiday (for now) to the Portland Trail Blazers, and a whole bunch of other stuff to the Phoenix Suns feels like it affected almost every team in the league. Here’s a look at several different angles of a trade that should help shape the NBA’s 2023-24 season … and beyond.
How the Bucks Are Affected
Let’s start in Milwaukee, where a contender that won the title two years ago was a month away from entering the 2023-24 season with more pressure than its aging, injury-prone shoulders might’ve been able to carry. When the Bucks traded Eric Bledsoe, three future first-round picks, and two pick swaps for 30-year-old Jrue Holiday back in 2020, it seemed like they were all in to get Giannis Antetokounmpo that elusive first ring. Well, not quite. Weeks after Antetokounmpo sent a clear message to his organization about how urgently everyone involved needs to treat the present, now it’s safe to say the Bucks are all in.
After a disastrous first-round exit (that ironically came against the Heat), last season’s starting backcourt of Holiday and Grayson Allen are gone, along with Milwaukee’s 2029 first and swap rights in 2028 and 2030. Change isn’t always necessary. Here, it’s a humongous short-term win for the Bucks, a franchise that needs to maximize Antetokounmpo’s prime and understands that long-term plans are irrelevant if its best player’s demands aren’t a top priority.
Put in the simplest terms, Milwaukee just plopped one of the best offensive players in the league onto one of the league’s best defensive teams. Granted, they’ll take an obvious hit at the point of attack, going from an elite on-ball pest to an undersized liability. (The loss of Jevon Carter, who signed with the Bulls this summer, stings a tiny bit more now.)
But efficient offense has been Milwaukee’s closest thing to an Achilles’ heel for the past several postseasons—including when it won the title despite not being able to score against the Nets in Round 2. Holiday wasn’t the sole reason for those struggles, but he’s always been a tad too erratic with the ball, someone who burned too many possessions with an inefficient quick trigger.
Enter Lillard, who averaged 32.2 points with a 64.5 true shooting percentage and a first-overall ranking in offensive estimated plus-minus. This dude guarantees great offense regardless of who’s around him. Now armed with ideal weapons at his disposal, Lillard has never been more dangerous. A perpetual long-range threat off the bounce who can/will get downhill against schemes that work to take away his deep range, the 33-year-old must be tracked the moment he crosses half court. The gravity he’ll have running pick-and-rolls with Giannis, Brook Lopez, and even Bobby Portis is a side plot in a Jordan Peele screenplay. Horror at this scale defies explanation. There are no answers.
Switch, and there’s a near-definite chance either Lillard or Giannis will have a mismatch. Drop, and Lillard hits a 3 in your eye. Blitz him, and have the good fortune of trying to stop Antetokounmpo from rumbling into the paint on a four-on-three. Now picture those two on one side of the floor with an empty corner. It simply can’t be defended with two people, which allows someone like Khris Middleton to feast in ways he basically never has before. Malik Beasley, Jae Crowder, and Pat Connaughton won’t ever be more open than they’ll be this season.
Milwaukee is now probably the favorite to win the East, but that doesn’t mean there aren’t real questions, especially on the defensive end, where teams will repeatedly put Lillard on an island in the playoffs. The Bucks should be awesome on defense, but the system they’ll deploy with rookie head coach Adrian Griffin is a total mystery, and their personnel isn’t as fierce as it once was. When Antetokounmpo and Lopez are both off the court, they might not have one plus defender/athlete. Another win-now move to address their leaky perimeter feels possible, if not likely. (Recent first-round pick MarJon Beauchamp and salary filler, anyone?)
The Bucks are also still pretty old, a concern that includes Lillard, who’s coming off his finest season but is just two years removed from an injury-plagued campaign that provided a glimpse of what he’ll look like when age-related decline eventually slows him down. Middleton’s durability is a question mark, and Lopez (who played a whopping 2,373 minutes last regular season) will turn 36 in April. But status quo clearly wasn’t an option.
Milwaukee took a risk three years ago when it pushed almost all of its chips in for Holiday. Now, the same thing is happening at an equally precarious time, with time no longer on its side. But the gamble is worth it. Lillard and Giannis are that good, and their best-case scenario is an offense with no ceiling.
How the Suns Are Affected
Speaking of offenses with no ceiling: If the Bucks are favorites in the East, this trade puts Phoenix in the same spot out West. Regardless of what you think about Deandre Ayton’s potential or talent, his contract and individual aspirations made for an awkward fit beside Devin Booker, Bradley Beal, and Kevin Durant. The thought of him disrupting their chemistry or derailing their defense by sulking on account of not getting the shots/touches he desires made him expendable.
How much of a hit they take on defense, going from Ayton to Jusuf Nurkic (who’s perennially hurt), is almost beside the point when you consider that aforementioned downside and what this team needs to win it all. This is a rewarding exchange for Phoenix. Depth is still the name of the game, and the Suns just turned a possibly disgruntled center into several role players who can help them win a playoff game/series. (Also: Phoenix just slashed a lot of long-term money from its books.)
Nurkic, Allen, Nassir Little, and Keon Johnson is not a bad gain, even if it forces the Suns to waive Ish Wainright and Jordan Goodwin (two names on non-guaranteed deals who become expendable on a roster that currently has 17 players). Since his rookie year, Allen is a 40.1 percent 3-point shooter, and he’ll have plenty of open looks against teams that are trying to slow down the Suns Big Three. If their thought process to win the West is “score more efficiently than the Nuggets can and ask questions later,” then the Suns have potentially succeeded.
How the Trail Blazers Are Affected
Both conferences now have favorites, but the aftershocks of this deal don’t stop there. The Blazers landed a franchise center who complements Scoot Henderson and Shaedon Sharpe. In the context of fit and roster construction, this makes more sense than Tyler Herro, Tyrese Maxey, or even OG Anunoby.
The Blazers also have Holiday, whom they will likely flip for even more capital than the juicy future draft pick/swaps extracted from Milwaukee (which may be an actual crater in the ground five years from now). Every contender should want Holiday. He’s on an expiring contract, with a two-way skill set that makes him more seamless than Lillard. Portland should court a bidding war for his services, and it wouldn’t be crazy to think the Blazers can get at least two unprotected first-round picks in return.
Is there a world where the Blazers try to be competitive before the trade deadline, with a rotation that features Ayton, Henderson, Anfernee Simons, Jerami Grant, Holiday, Sharpe, and Matisse Thybulle? Maybe. But Holiday will definitely be on a contender by March.
How Jrue Holiday, His Many Suitors, and the Rest of the NBA Are Affected
The Clippers should do whatever they can to get Holiday in their practice facility. If that means including Terance Mann (whom I love) in a deal, so be it. This organization has never even reached the NBA Finals, and should be operating with the posture of a club that feels twice as much pressure as the Bucks. Go all in. Holiday is someone worth pushing every chip to the middle for. He’s a seamless fit beside Paul George and Kawhi Leonard on both sides of the ball, an established ball handler who can score and facilitate in myriad ways, then wreak havoc guarding whoever Ty Lue needs him to on the other end. James Harden he is not.
The Celtics have draft picks, but matching salary here would be tough. Malcolm Brogdon’s deal isn’t enough, and it’s unlikely (though not impossible) to see them adding Al Horford or Robert Williams III. The Sixers should definitely make a call, but their best offers can be beaten unless they’re willing to give up Maxey, which they won’t do.
The Bulls wish they could triple down on their goal of winning a playoff series, but don’t have room for another guard or the money to make anything realistic happen. The Raptors, fresh off losing Fred VanVleet for nothing, could be interested. But Holiday doesn’t move the needle for them in any meaningful way. Same goes for the Nets and Knicks. The Timberwolves and Mavericks don’t have the picks. The Thunder have more picks than they know what to do with and shouldn’t be counted out here. It’s not that Holiday would make OKC a contender, but imagine how suffocating the Thunder defense would be with him in the starting lineup. (If this exact scenario were presented to Sam Presti a year from today, he’d probably pull the trigger on a consolidation trade.)
The Kings are an interesting wild card. Harrison Barnes, Kevin Huerter, Chris Duarte, and an unprotected first-round pick in 2027? The Warriors can’t be ruled out. Chris Paul, Jonathan Kuminga, and their first-round pick in 2027? Several key Lakers contracts (including Austin Reaves) aren’t eligible to be traded for a few months, so L.A. probably has no chance unless this drags into February. Holiday could help the Pelicans, but he doesn’t line up with their timeline, and it’d be weird to see them give picks up for the same player they dealt for a bunch of picks three years ago. (Sidebar: This is not the best day for New Orleans, considering it owns the Bucks’ unprotected first-round pick in 2027 and swap rights in 2024 and 2026.)
This brings us to the elephant in the room: Miami. Lillard going to the Bucks is beyond catastrophic for a Heat team that (a) was Lillard’s strong preference; (b) the clubhouse favorite to land him all summer; and (c) lost Max Strus, Victor Oladipo, and Gabe Vincent because re-signing them would’ve complicated any trade for Lillard. Miami will front like it has enough to make another Finals run. Maybe it’s right! Any team with Erik Spoelstra, Jimmy Butler, and Bam Adebayo should feel very confident. But the fact that Lillard landed in Milwaukee and placated a two-time MVP who might otherwise have been disgruntled enough to land in South Beach sooner than later is a double whammy of epic proportions. (This is a big deal for any team that was saving assets for a potential Giannis trade. Clubs may be less precious with their picks on the trade market than they otherwise would’ve been.)
Does surrendering multiple assets for Holiday even make sense, particularly if Herro is involved? How much better are they with Jrue spending key possessions as a spot-up threat? All this depends on what they’re willing to offer to a front office that will not be receiving a Christmas card from the Riley family anytime soon.
But what’s a massive disappointment for one hopeful contender is another’s cause for celebration. The fallout from this blockbuster won’t be known for quite some time. But in the here and now, what we know is the NBA landscape looks a lot different than it did 24 hours ago.