The Bucks win the offseason at the buzzer
It was Dame Time in the NBA offseason.
With less than a week before Media Days, the Milwaukee Bucks swung a trade for Damian Lillard, who netted a career-high in scoring last season with 32.2 points per game, who is easily a top-15 player in the league, who has hit too many clutch shots over his career to count, who pairs with Giannis Antetokounmpo to make the Milwaukee Bucks eminent title favorites, soaring above the Boston Celtics, Denver Nuggets, Phoenix Suns, and other contenders. If ever an offseason move was a buzzer-beater, this was it. Hopefully it begets many more clutch buckets for Milwaukee in pursuit of a second title of the Giannis era.
To get Lillard, the Bucks surrendered point guard Jrue Holiday, who was key in their 2021 NBA Finals win, Grayson Allen, and a 2029 first-round draft pick. They agreed to pick swaps with Portland in 2028 and 2030 (which Portland is unlikely to find useful). They also got help from an unlikely source: the Phoenix Suns, whom the Bucks beat to win the championship two seasons ago. The Suns swapped DeAndre Ayton for Jusuf Nurkic, Nassir Little, and Keon Johnson as part of the deal.
Milwaukee was the little engine that could in Damian Lillard trade talks, as Lillard’s stated preferred destination, the Miami Heat, held too tightly to their leverage and ultimately allowed Portland to find a trade partner that better met their needs. The trade feels eerily similar to the Donovan Mitchell saga of a year ago, where the New York Knicks and Brooklyn Nets squandered leverage and allowed the Cleveland Cavaliers to swoop in unexpectedly to land the star guard.
The addition of Lillard completely reframes the picture for Milwaukee on offense. It gives Milwaukee two legitimate scoring superstars to feed. While Holiday was a threat to score and could create his own shot, Lillard can fold a defensive scheme in on itself. Give him a powerful outlet like Antetokounmpo to work with, and the possibilities are endless. He also provides a steady hand to initiate offense for Milwaukee in crunch time. The symbiosis between Antetokounmpo and Lillard — presenting each other’s weaknesses as their own strengths — makes the duo intensely promising. Antetokounmpo will handle the ball less, draw defenses away from Lillard on the attack, and provide (along with Brook Lopez) the best interior defense Lillard’s ever had in his career. Lillard will open things up for Antetokounmpo, reduce the need for Antetokounmpo to keep defenses honest by hoisting threes, and provide the best clutch scorer Antetokounmpo has ever been paired with. These basic shifts will allow each player to elevate the things they already do well. All of this without mentioning Khris Middleton, who would have been Lillard’s best teammate in Portland.
The Bucks did well to depart with relatively few assets. They kept Pat Connaughton and Marjon Beauchamp, helping the bench remain viable. They’ll likely work with lineups featuring Lillard, Khris Middleton, Antetokounmpo, Brook Lopez, and one of Connaughton, Beauchamp, or Jae Crowder, depending on how much size they want to feature and how Crowder is coming along after a partial season with Milwaukee in which he saw the floor very little. Whichever two don’t start will join Bobby Portis in coming off the bench as part of the rotation, as well as spot work for Malik Beasley or a point-guard-to-be-named-later. Cameron Payne, Austin Rivers, Ish Smith, Goran Dragic, and Michael Carter-Williams are available (not that any of those options appeal to the Bucks).
Responsible for fitting the pieces together is new head coach Adrian Griffin, who earned the endorsement of Antetokounmpo over the course of the Bucks’ coaching search. One of Griffin’s major moves as Bucks coach so far was the hiring of former Blazers head coach Terry Stotts, who reunites with Lillard after coaching him for nine seasons in Portland. The two joined the Blazers together in 2012 and do the same in Milwaukee 11 years later. Presumably, Stotts’ presence will help the Bucks staff earn Lillard’s trust. Lillard also reunites with Robin Lopez, who was Portland’s starting center in the early years of Lillard’s career.
For the Bucks, the loss of Holiday is one they’ll feel off the court more so than on. It’s very rare that Milwaukee willingly moves on from players of Holiday’s caliber; the last such move was trading a prime Ray Allen for an aging and disgruntled Gary Payton, who forced his way out soon after. This time, the Bucks traded their bigger fish for an even bigger fish, instead of downgrading. Holiday’s place in Bucks history is secure, as his addition brought Milwaukee its first title in 50 years, with his signature steal of Devin Booker and alley-oop to Antetokounmpo providing one of the greatest moments in franchise history.
Holiday’s place in the league, however, is far more uncertain. The Blazers will likely look to move Holiday for an enticing return package, thus augmenting their gross return for trading Damian Lillard. Holiday could be a target for teams who lusted after Lillard, Miami, Toronto, and Brooklyn, or another suitor like Philadelphia, Chicago, or New Orleans. Holiday has proved he can be the third-best player on a title team, and brings menacing perimeter defense without needing the ball as much as Lillard did. While it’s possible Portland could use Holiday to mentor Scoot Henderson and a young Blazers team, he’s ultimately probably headed elsewhere.
If not for the Holiday-Lillard swap, a deal involving DeAndre Ayton for Jusuf Nurkic would still qualify as a blockbuster trade in an NBA offseason that has been wanting for player movement (counter to the last, oh, 15 years). Ayton, long dissatisfied with his station in Phoenix, gets a fresh start anchoring a young Portland team. He’ll be an integral piece of their offense, giving Henderson, Anfernee Simons, Jerami Grant, a really interesting offensive chess piece to work with. Nurkic, meanwhile, provides a big presence in Phoenix that won’t crave as big a role as Ayton would have. Nurkic seems to be working to add a 3-point shot to his game, as he hit 36.1% on a career-high 2.3 attempts per game last year. Leaning into that element, which Ayton does not provide, might allow more space beneath the arc for midrange specialists Devin Booker, Kevin Durant, and Bradley Beal to operate. The Suns also added Grayson Allen and Nassir Little, two veteran wing options that give the Suns added depth. Overall, the Suns made out really well as a broker for the Lillard deal, exchanging Ayton’s proficiency as a scorer, much of which likely would have gone to waste, for spacing and some much-needed depth.
The Bucks landing Lillard registers as a shock, as the Lillard-to-Miami trade seemed a foregone conclusion since the moment the Nuggets won the championship and Miami faced the prospect of their offseason. For the Heat, the failure to get a deal done comes down to not having desirable pieces — the best package they could offer was Tyler Herro, Kyle Lowry, Nikola Jovic, Jaime Jaquez, and two first-round picks, which is pretty bad if you aren’t excited about Herro like Portland reportedly wasn’t — and perhaps its own stubbornness. There was widespread rumors that Miami wasn’t willing to offer that full package, or was content to wait out the Blazers and strike a deal when it became clear Lillard wouldn’t be willing to go anywhere else. Only that talk, which came so loudly from Lillard’s camp that the NBA issued a cease and desist memo to the parties involved, wasn’t equal to reality. Of course Lillard is going to get excited about the prospect of winning a championship alongside Antetokounmpo in Milwaukee — he was willing to play in Portland with Jerami Grant and Anfernee Simons. This is much better for him.
Beyond that, the national discourse disregarded the possibility of Lillard going anywhere outside Miami at large, and even when they did, they precluded Milwaukee from the conversation.
From ESPN’s Zach Lowe: “You mention Milwaukee… I just, I can’t see it. I mean I get why they would look into it for sure, I mean the pressure that is on them now is extraordinary. They have Jrue Holiday, and they have I believe one first-round pick they can trade. … I just don’t know that Jrue Holiday on an expiring deal is fetching the Blazers, through a third team, the kind of bonanza they’re gonna want.”
ESPN ran a story outlining three non-Heat trade possibilities for Lillard. The Bucks were not included. The Philadelphia 76ers, New Orleans Pelicans, and the Toronto Raptors were the options.
Why weren’t the Bucks included? The question is particularly interesting on the heels of Antetokounmpo deliberately applying pressure to the front office of the Bucks in the New York Times (in what I’m not realizing is the last New York Times sports story of significance), saying he wouldn’t sign an extension in Milwaukee if the Bucks didn’t show a full commitment to winning another championship. For some reason, national media outlets interpreted that as heralding an exit from Milwaukee, not heralding a splashy move by Milwaukee to keep Antetokounmpo in town. I mean:
He’s kind of a big deal there!
Plus, Milwaukee was able to do this because they had Jrue Holiday, and national outlets seemed to forget that Bucks GM Jon Horst already made a big splash acquisition when the franchise’s back last seemed against the wall, on the heels of a crushing conference-semifinal defeat in the Bubble against Miami. Holiday’s presence helped Milwaukee crush Miami the following year en route to a title. Back under the thumb of the Heat, Horst again made a move to get his team good enough.
It’s a sad departure for Milwaukee, losing Holiday. It was just Tuesday that the Milwaukee Journal-Sentinel’s Jim Owczarski published an interview with Holiday in which he reaffirmed his commitment to Milwaukee, saying he wanted to retire a Buck: “Before I even won here, I think I said I’m a Buck for life, and I mean that like deep in my heart.” You’d wish the trio of Antetokounmpo, Holiday, and Middleton could have stayed healthy and given themselves a chance to repeat, or redeemed themselves this season when they had the chance. They missed that chance, though, and it was time to try something new or stagnate. Antetokounmpo is the foundation. Middleton was a restricted free agent whose value, because of injury, was far less outside of Milwaukee than in Milwaukee. It was Jrue Holiday who was expendable, who could be used to swing for something bigger. You hate that it had to be Jrue, but it had to be. Had to.