When Giannis Antetokounmpo put the Milwaukee Bucks and the league on notice — twice — the Bucks had no choice but to explore what role player upgrade they might get for the only first-round pick (its 2029 selection) it could trade outright.
The challenge in such an incremental move would be finding a player who would nudge the needle enough to surrender that pick with light protections, plus the needed matching salaries — likely those of Grayson Allen and Pat Connaughton, presuming the Bucks would not break up their championship core.
Skeptics within the league wondered: Why burn that pick in an inconsequential move when the Bucks could wait until this offseason and bundle more picks in a game-changing trade?
The reality is that the Bucks did not have that time nor the luxury of waiting to see this season play out and failing again (and, yes, last season was a failure). The risk of Antetokounmpo requesting a trade would be too great. Potential suitors were already gearing up.
And so in an NBA earthquake, the Bucks dispensed with the incremental moves and reached for an improbable blockbuster: swapping Jrue Holiday, the two-time All-Star they acquired the last time Antetokounmpo’s future in Milwaukee appeared uncertain, that 2029 pick, and two unprotected first-round picks swaps (2028 and 2030) to the Portland Trail Blazers for Damian Lillard — the main part of a three-team (for now) megatrade that also sent Deandre Ayton to the Blazers, with Jusuf Nurkic and role players from both Milwaukee (Allen) and Portland (Nassir Little) headed to the also-all-the-way-in Phoenix Suns.
It is a trade that both keeps Lillard away from East rivals — notably the Miami Heat, Lillard’s top choice — and deals at least a partial blow to teams hoarding assets for any future Antetokounmpo pursuit. One of those teams may end up nabbing Holiday as a consolation prize, though his market will be very wide, league sources said Wednesday. With Lillard, the Bucks reassert themselves as favorites in the East.
Milwaukee is trading two starters for one, and one of the league’s best perimeter defenders in Holiday for a minus at the point of attack in Lillard. Connaughton seems the best candidate to slide into Allen’s fifth starter role. Connaughton is stouter than Allen on defense, but the Bucks no longer have a bonafide wing “stopper” type to guard Jayson Tatum, Jaylen Brown, Jimmy Butler, and the other elite wings in the East. (Butler just cackled reading that sentence given the meanness he unleashed on Holiday in the playoffs — even if Butler’s Heat could enter the Holiday derby, per league sources.)
Khris Middleton has lost a quarter-step, and was never a stopper anyway. Jae Crowder is 33 with declining foot speed, and has to find his game again after a lost season. The Bucks need Crowder now. MarJon Beauchamp has shown glimpses on both sides, but stepping into a heavy-minutes role on the biggest stages is a lot to ask of any second-year player. Antetokounmpo has always been more comfortable as a rover and rim protector — though that was in part Mike Budenholzer’s preference, and the Bucks have a new coach in Adrian Griffin.
Chipping away at their perimeter depth might make it harder for the Bucks to get to super-small lineups with Antetokounmpo as the only big. They might not care. Those lineups did not play that big of a role in Milwaukee’s 2021 title run, and faded in relevance a bit with P.J. Tucker’s subsequent departure — and Bobby Portis’s emergence as one of Milwaukee’s most important players. If anything, the new-look Bucks may have to experiment with Antetokounmpo, Portis and Brook Lopez playing together a bit more in ultrabig groups.
Over a half-decade of contention, defense has been Milwaukee’s keystone. The Bucks will take a step back there. Having Lopez hang near the rim, a snarling forcefield, was contingent to some degree on Milwaukee’s guards getting around picks unscathed — so that ball handlers did not have clean pull-up 3s or unfettered runways on the other side of those picks. That scheme might wobble now.
The trade-off on offense is worth it. Lillard doesn’t merely boost Milwaukee’s half-court offense — its weak link even in that 2021 title run, its undoing in every other postseason. He allows for a total reimagining of it. He is, by himself, damn near a walking top-five offense. Milwaukee’s defense should be good enough and then some as long as both Antetokounmpo and Lopez — two Defensive Player of the Year candidates last season — are on the floor at go time.
The Lillard-Antetokounmpo pick-and-roll — with everyone else spotting up around it — becomes a supercharged version of the Middleton-Antetokounmpo two-man game that was Milwaukee’s tentpole in their championship season. That partnership drifted away from the Bucks amid Middleton’s injuries and his uneven play upon returning last season. It was not something they could count on as they unraveled in fourth quarters against Miami in the first round. Holiday’s decision-making and overall offense were scattershot in every Milwaukee playoff run.
Lillard is the second-most-talented pull-up 3-point shooter in NBA history, behind only Stephen Curry. He is the ballhandling failsafe Milwaukee has not had in two years, and never really did. Even in Middleton’s best seasons, the Bucks got by in the half-court — relying more on Antetokounmpo’s transition thunderclaps and brutish offensive rebounding. With Lillard, the Bucks can run pick-and-roll from more spots and far-flung places — stretching defenses to their breaking points. They can ease Middleton into a third option role for which he is better-suited now.
Every season, Lillard gets cagier as a driver and playmaker. He’s not an A-plus passer, but he’s very good — steadier than anyone Milwaukee has tried in that role across Antetokounmpo’s prime. Lillard takes care of the ball and gets to the line a ton — almost 10 times per game last season, a career high.
When Antetokounmpo wants to cook, Lillard is as intimidating a floor-spacer as exists outside the Bay Area. Watch out for the inverted Antetokounmpo-Lillard pick-and-roll, especially in semitransition. Good god.
This will require some buy-in for Antetokounmpo. Is he willing to set 30-plus picks in big games — to be Lillard’s screener for long stretches? How will he feel when it becomes clear the ball starts and often ends with Lillard in crunch time?
As Kevin Pelton noted, the Bucks are now naked in terms of future draft picks — vulnerable to catastrophe if this somehow fails and Antetokounmpo wants out. But they could recoup tons of picks by trading Antetokounmpo in that nightmare scenario, and still more by trading (if need be) Lillard.
For now, they are favorites again in a jumbled East. The pressure of Antetokounmpo’s future quiets some. They can play in relative calm. They were already more than half-in via the original Holiday trade. Given the signals Antetokounmpo had sent, going all the way was the right choice. Antetokounmpo is 28, with many more years left in his prime and not much injury-related concern (despite undergoing a knee procedure last summer.) He is the franchise.
The Heat are left standing at the altar, though they and the Blazers might have never even arrived at the chapel. The two sides appear to have had no meaningful dialogue — and maybe none at all — since late July, per league sources. The Blazers had no major interest in any individual Miami player or draft asset, and limited interest in whatever combination Miami might cobble. The sides were far apart in initial talks, sources said. The Heat were reluctant to toss in every player and pick and swap the Blazers might have wanted in the end — some or all of Tyler Herro, Nikola Jovic, Caleb Martin, Jaime Jaquez Jr., filler salary, multiple picks, multiple swaps.
(There is a tendency to devalue Miami’s future first-round picks under the assumption the Heat will always be good — their picks therefore low — because the Heat are generally good. That is true until it’s not, and the Heat with Lillard and Butler would have had some downside risk in outlying years.)
Did the Heat play it too cool, confident the messaging from Lillard’s camp would do the work for them? Did that messaging backfire on Lillard, poisoning the Miami-Portland waters before talks could even start? Did it matter? Even if Miami had caved — if the Blazers had gone back to them in the end, and wrenched everything away — Portland may have looked elsewhere. Talks never got far off the ground.
Trading everything for Lillard would have left the Heat thin around Lillard, Butler and Bam Adebayo — a big three so perfect, so complementary in almost every way, as to be borderline obnoxious. You can understand the Heat’s confidence on some levels. This team with two stars — Butler and Adebayo — has made two of the past four NBA Finals, and came within one Butler in-and-out jumper of making three of four. They lost Max Strus and Gabe Vincent, but they get Herro back healthy; Jovic coming off a nice FIBA World Cup for Serbia; a ready-to-play rookie in Jaquez; a more experienced Haywood Highsmith; a full season of Kevin Love; and a couple of plug-and-play bench veterans in Josh Richardson and Thomas Bryant. (Keep an eye on Orlando Robinson, too.)
Why should they be scared of anyone? Why shouldn’t they bet on themselves again?
That said, they won 44 games last season and barely escaped the play-in tournament. Butler just turned 34. They preserved their chips for another day — you may have heard stars with wanderlust enjoy Miami — but they also need to win now, and that Big Three with threadbare depth around it would have been formidable. The Bucks increased their chances of retaining Antetokounmpo for longer. Several teams are hoping Joel Embiid eventually shakes loose from Philadelphia, but he plays the same position as Adebayo.
Miami has so far shown limited interest in James Harden as a Lillard consolation prize, but what about Holiday? As Brian Windhorst notes, expect Holiday and the Blazers to have a range of trade options — perhaps including Miami, Philadelphia, the LA Clippers, and others. (Two under-the-radar teams that could make good Holiday fits and are expected to have at least some level of interest, sources said: the Indiana Pacers and New York Knicks. The Pacers may determine in the end that the price is too high, and that it’s too soon to flip future assets for veterans.)
Given the bonanzas fetched for Rudy Gobert, Kevin Durant and Donovan Mitchell, turning Lillard into only one unprotected first-round pick and two swaps might feel disappointing. But those were always apples-to-oranges comparisons. Lillard is a 33-year-old small guard on a massive long-term contract — distinct from Mitchell in age, and Durant in size and skill set. Several teams with the players and picks to make a legitimate run at Lillard never really waded into the proper bidding, league sources said.
The Gobert deal is an outlier from a now-defunct collective bargaining agreement, a trade so risky that it became an almost instant market correction — a constant, nagging second-thought for any general manager who feels temporarily exuberant about flinging away picks. Portland will turn Holiday into draft equity, and eventually be able to say it traded Lillard for a former No. 1 pick (Ayton) and five or six draft assets. Time to move on.
There has to be some level of dissatisfaction in Miami with how all this unfolded, if not full-on regret. Time will tell if Miami missed here. The Heat are never done.
The Suns never appear to be done either, not even when they are out of first-round picks and had to split up swap rights in order to scrounge up some second-rounders.
Swapping Ayton for Nurkic is a fascinating bet. On talent, it is a downgrade. Ayton is younger, faster, nimbler and more versatile on defense, a better shooter (though Nurkic dabbled in 3s last season for the first time in earnest) and rim protector. Nurkic has not played more than 56 games since 2018-19, and missed significant time last season with a calf injury.
The Suns will score like gangbusters, but they have to be at least passable on defense to win four playoff series. A resurgent season from Ayton was their best chance at gluing everything together on that end. The burden now falls to Nurkic.
It is a risk, even with how badly it ended for Ayton last season in Phoenix — supplanted at times by Jock Landale, a journeyman. But in rewatching all of Ayton’s pick-and-roll reps on defense from last season’s playoffs, it was clear Ayton was better than I had remembered or thought at the time.
He floundered on offense. He was tentative, spinning away from the rim and stopping short of contact to the obvious frustration of teammates and coaches. He rarely gets to the line.
Nurkic is a poor finisher around the basket, but he goes for it with more gusto and power. He is a slightly better passer than Ayton on the move, in the flow of pick-and-rolls, Nurkic will make the right read faster and more often when defenses trap Durant, Devin Booker and Bradley Beal high on the floor.
Perhaps Nurkic will be content setting endless screens and rolling hard to the basket, often without tangible reward. Ayton did that because it was asked of him, and often did it quite well — well enough to help the Suns to within two wins of the championship in 2021. But there was always a sense within and around the team that Ayton wanted more, and would never get it in Phoenix. (It will be interesting how the Blazers strike this same balance with Ayton, given they are building around several ball-handling guards and wings in Scoot Henderson, Anfernee Simons, and Shaedon Sharpe.)
Monty Williams, then the Suns head coach, benched Ayton for most of the team’s Game 7 humiliation at home against the Dallas Mavericks in the second round of the 2022 playoffs. Ayton was dealing with a rib injury in the lead-up to Game 6 of the Suns’ second-round series against the Denver Nuggets last season, and ended up missing the game.
It might have been too far gone for Ayton and the Suns, despite a new coach (Frank Vogel) eager to repair the relationship and a revamped roster of new teammates. If so, getting Nurkic and two rotation wings — Allen and Little — is a good enough return. Ayton is a worthwhile get for Portland. He’s good, and fits their timeline — a talent worth trying to redeem.
Nurkic can’t match Ayton’s speed and verticality on defense, but he has been a sturdy back-line presence when healthy. Even in seasons in which their defense was mediocre or bad, the Blazers tended to defend much better with Nurkic on the floor — often holding opponents to stingy efficiency levels. They trusted Nurkic enough in the paint to have perimeter defenders stick close to shooters, and rarely fouled when he played.
Allen is an elite 3-point shooter (39.5% career from deep) who can come off the bench for Phoenix, so that he is not as overtaxed on defense as much as he was starting in Milwaukee. Like Keita Bates-Diop, Little represents a smart shot at an archetypal 3-and-D player. Little hit a career-best 37% on almost six 3s per 36 minutes last season, and has a little pump-and-go playmaking oomph to his game. He’s 6-6 with a giant 7-1 wingspan and the ability to switch across four positions on defense. He could end up the sneaky prize of this deal for Phoenix, and even get a chance at some point at that fifth starter spot if his shot continues to develop. (That may sound far-fetched, but if Bates-Diop is a candidate there — and he is — then Little can be, too.)
Little and Allen are also on handy midsized salaries that could work well in trades in the last season before teams over the second apron (as Phoenix is) can aggregate salaries in deals.
The Blazers had a franchise player to trade; the Bucks and Suns approached them from two different angles with the same underlying urgency to win now. This megadeal will birth another title-altering trade involving Holiday, and could end up a win for all three teams involved.
