Where was everybody?
It was late September inside the Milwaukee Bucks’ offices that sit across the street from Fiserv Forum, and the team’s basketball operations brain trust — from general manager Jon Horst on down — was nowhere to be found.
This was not normal.
Had they taken unexpected vacations? Was there a company retreat that the employees who were left behind, and who had certainly noticed the three-day absence of the team’s front office core, weren’t invited to? It was all so confusing.
Advertisement
Then came the stunning news that solved the intra-office mystery: The Bucks had landed Damian Lillard from Portland in a three-team deal that sent Jrue Holiday, an unprotected 2029 first-round pick and two pick swaps to Portland and Grayson Allen to Phoenix.
For the second time in less than three years, with uncertainty about Giannis Antetokounmpo and his long-term future in Milwaukee looming and the two-time MVP appearing to apply pressure through various media channels in the month before the deal, Horst responded by pulling off the kind of gutsy, blockbuster trade that relieved the pressure that comes with employing a superstar. And he did it while turning the team’s locker room into a temporary headquarters during those crucial final three days that led to the deal.
Secrecy is paramount when it comes to moves of this magnitude. One stray piece of information, or an ill-timed media leak, can change the state of negotiations or perhaps kill a trade entirely. If there is no deal to be done, then it’s vital to keep the details of those discussions private to protect the spirit of the players discussed and, by proxy, the group. In this case, where the Bucks already had a roster they still believed to be legitimate title contenders, that meant keeping the Holiday part of the discussion with the Trail Blazers under wraps.
For the 40-year-old Horst, who joined the Bucks’ basketball operations group in his mid-20s and was elevated to GM in 2017, this sort of temporary office relocation was one of the many ways he has learned to be discreet. Even Antetokounmpo, who had made the Bucks faithful so nervous when he spoke openly about the prospect of leaving Milwaukee with the New York Times and on the “48 minutes” podcast, didn’t know that the trade was in the works.
“No idea,” Antetokounmpo told The Athletic recently. “No idea. But I understand why, because Jrue Holiday is my guy. And I don’t want (to be part of that process). I don’t do this.
“I was lifting weights (at the practice facility) with the strength and conditioning coach (Suki Hobson), and Suki said, ‘Oh!’ (as she looked at the news on her phone). And I said, ‘What’s going on?’ And then she showed me.”
When it comes to Antetokounmpo’s influence within the organization, he decided years ago to steer clear of the moves that involve someone being sent away, i.e. firings and trades. That doesn’t mean his viewpoints aren’t known internally, of course, as is the case with any superstar. And as was the case in the coaching search process that led to the hiring of Adrian Griffin last summer — when Antetokounmpo endorsed the move after taking part in a Bucks dinner to discuss the possible hiring — he’s willing to be more intimately involved when the key decision being made doesn’t result in anyone’s exit.
Advertisement
But his trust in Horst, who was part of the John Hammond-led front office that drafted Antetokounmpo as an 18-year-old in 2013, runs deep.
“I’ve said many times that I don’t want to be aware of things that affect people’s lives,” Antetokounmpo said. “At the end of the day, if you trade somebody it affects his life, or if you fire somebody, it affects his life. For me, I cannot be a part of that. And I want to stay away. From the early years, 2016, 2017, with the first conversations, (Bucks officials would) say, ‘Giannis, what do you think about this?’ (He’d say), ‘Guys, I’m going to take a step back in this. What I want to know is that we always have a chance to win. I trust you guys, and you guys are going to do that. And I think Jon has done a great job doing that for years now.”
GO DEEPER
Inside the Damian Lillard trade to Milwaukee and how it came together
So why, then, did it seem as Antetokounmpo was so skeptical of the Bucks’ willingness to go all in when he did those two summertime interviews? Was it part of a plan to compel the Bucks front office to make a big move such as the Lillard trade this summer, or perhaps a way of nudging them to give Holiday an extension that seemed to be in question as the All-Star guard approached possible free agency next summer? To hear Antetokounmpo tell it, it was none of the above.
“No. Zero. None of those things,” Antetokounmpo said emphatically during our post-practice discussion. “It was organic. I didn’t have a strategy. Nothing. (That message) is something that I always — every year — say. I can go back and find five articles of me saying this since I was 22 years old, you know?
“The New York Times piece was not about basketball. It was a business piece, and (the reporter), like everybody else, cut to the chase and asked me a basketball question and I said what I always say. And the podcast, I went on this podcast because the (host, former Bucks assistant coach Ross Geiger) is my friend. He’s a guy who, when I came into the league and I was 18 and nobody was talking to me, he took care of me. I slept on his couch. He helped me when I got groceries. He allowed me to drive his car because I didn’t have a driver’s license. I only had (a permit), where I took a test and I could drive with somebody in the car. So he was always that guy in the car. We’d go and get food. He. took me to the game, took me to the practice every day, so it was the least I could do.”
Advertisement
From Horst’s vantage point, there was nothing new to be learned by way of Antetokounmpo’s media tour. The 28-year-old was merely saying publicly what had been known within the Bucks privately for so long now. This is the welcome reality of having one of the game’s greats on your roster.
Still, Horst admits that it played a small part in his level of urgency with the roster.
“I think it’s probably too dismissive to say that (Antetokounmpo’s comments) didn’t factor in at all,” Horst told The Athletic. “That’s probably not honest and sincere, because I care about everything that our players say and I try to assess it and evaluate it and understand it. But (the part it played) is just a little bit above ‘not at all.’ It’s not much above ‘Not at all.’ And the reason is that it’s not new.
“It’s nothing that he hasn’t said to me privately, that he hasn’t said publicly (before). It’s nothing different than how I believe and feel and operate, obviously, considering the things that we’ve done. We’re obviously very aligned in our approach, in our commitment to winning, to not being just OK and standing pat or accepting the status quo. So it had very little impact on what we did. What we did is because we felt like it was the best thing for us to do.”
Besides, the factors that truly matter had already been driving this conversation long before Antetokounmpo sparked so many headlines with his media messaging.
Ever since the ownership change that unfolded in April — and even before — there had been a significant uptick in league-wide speculation about Antetokounmpo’s future in Milwaukee. Longtime Bucks co-owner Marc Lasry, who had primary control of the team when Milwaukee won it all in 2021 and who was close with Antetokounmpo and his family, sold his 25 percent stake in the team to Cleveland Browns owners Jimmy and Dee Haslam.
Behind the scenes, it was an open secret of sorts that Lasry’s concern about Antetokounmpo eventually leaving was a factor in the decision because, well, it would certainly impact the organization’s valuation if he left town. Yet when asked to address the speculation about Lasry’s concern, and the general idea that the sale was partly motivated by a belief that Antetokounmpo would eventually leave, Antetokounmpo strongly disagreed.
GO DEEPER
How Damian Lillard transforms the geometry and gravity of Milwaukee's offense
“It’s false,” he fired back. “I want to stay. But I want to stay in a winning organization. That’s false. But I get it, because he’s a businessman.”
A businessman who was part of the group that bought the team for $550 million in 2014 and sold at a valuation point of $3.5 billion nine years later.
“That’s what business people do,” Antetokounmpo continued. “There were a lot of bills coming. The salary cap was going up. And at the end of the day, s—, if I (buy in) on a team (and) you sell to get (that kind of return), I’d probably do the same thing. It’s business.”
Advertisement
The financial factor certainly loomed large.
With the sweeping changes to the league’s collective bargaining agreement making it more punitive than ever to pay the title-contending freight, owners the league over have been forced to reassess the risk-reward calculus of it all. For the Bucks, it all starts with Giannis.
After choosing to bypass the three-year option worth an estimated $169 million that is available to him now — $117 million of which would be new money — Antetokounmpo will be eligible to sign a four-year extension worth a minimum of $234 million next summer. On his current contract, he could opt out in the summer of 2025. And despite not knowing for sure if he’ll be willing to sign another deal anytime soon, there was a dire need to invest heavily all around him so as to maintain his faith.
So three-time All-Star guard Khris Middleton was re-signed on a three-year, $102 million deal in the summer. Lillard’s deal, which runs through the 2026-27 campaign and has a player option in the final season, is worth a combined $216 million. After all of the Bucks’ offseason moves, which included the re-signing of center Brook Lopez on a two-year, $48 million deal, they have the league’s fifth-highest payroll this season at $183,584,668. (The salary cap for this season is approximately $136 million, with the luxury-tax level approximately $165 million.)
Antetokounmpo, in turn, is clearly pleased with the way the Bucks have done business of late.
“I feel very good about it. I think it’s going to pay off,” he said with a smile about the Lillard trade. “But at the end of the day, we’ve got to be about it. We’ve got to play about it. We cannot talk about it.”
Especially before the deal was done.
By the time late September rolled around, Lillard had long since given up hope of landing in Miami. The acrimony between his camp and Trail Blazers general manager Joe Cronin had reached a point of no return, with Lillard convinced that it had become so personal between them that a future with the Heat was not to be. Cronin had stopped communicating with Lillard’s agent, Aaron Goodwin, in mid-September. Even Lillard’s pre-training camp choice to rejoin the Blazers — part of his plan to remain patient while Cronin worked closer to a deal — was met with resistance from Cronin.
Advertisement
“It was anything to go against what I would have wanted,” Lillard told The Athletic, “That part was irritating. Just based off how it was happening, I knew (it wouldn’t be Miami).
“(The Blazers) hadn’t talked to Miami. So once it started happening like that, then I started hearing about all these other random teams, I was like, ‘I’m probably not going to Miami.’ So I wasn’t holding on to that too (much).”
What he had done, though, was green-light a message to Milwaukee in mid-September that would have everything to do with what came next.
When Lillard was convinced that Miami was off the table, Goodwin wanted to know if the Bucks were among the teams in serious pursuit of his seven-time-All-Star client. They weren’t.
But when that backchannel blessing was given, with the Bucks learning that Lillard would be excited about a possible partnership with the Bucks, the chase was on. And so the work began for Horst and his small group of trusted front office associates.
Their days would often start before 7 a.m. and end after the local pubs closed at 2 a.m., with the Bucks analyzing the possible addition of Lillard — and the loss of Holiday and Allen — from every possible angle. The two-hour time zone difference between Portland and Milwaukee played a part in the late hours, as Horst wanted Cronin to be able to call and share ideas whenever he so pleased. For nearly two weeks, the process of landing Lillard consumed them.
There were constant conversations with the Bucks’ new ownership group, with Wes Edens and Jimmy Haslam kept abreast of the latest and free to share their views all along the way. Every discussion, and every new piece of information or revelation that came with it, was followed by another round of analysis and a revised action plan.
Near the end of the process, as the optimism grew that a deal might get done, there were pre-emptive party plans to be made. The Lillard welcome parade in Milwaukee that took place two days after the trade, for example, had been organized three days ahead of the deal.
Advertisement
Mostly, though, Horst and his front-office group needed that time to take a long, hard look at this prospect of saying goodbye to a beloved player and person in Holiday who played such a massive part in the Bucks’ title just two summers before. The 33-year-old is widely regarded as one of the best defenders on the planet. He is a gold medalist and made the All-Star team for the second time last season. On and off the court, he was revered within the organization.
More importantly for the Bucks’ purposes, they still truly believed that they could win another title with Holiday as a vital piece of their core. Lillard’s inclusion on the NBA’s Top 75 list was certainly impressive, but that status alone wasn’t enough to justify the move.
GO DEEPER
Damian Lillard opens up about trade to Bucks, 'cheat code' fit with Giannis
The question, in essence, was whether he was a better fit than Holiday within the Bucks’ system. And once the internal verdict was in, there was an unmistakable irony that came with their building excitement. If this goes according to plan, Lillard’s arrival will have the same effect as Holiday’s did nearly three years before.
When the Bucks landed Holiday from New Orleans in November 2020, there were similar forces at work relating to Antetokounmpo. Then, like now, he had been unwilling to sign a long-term extension while sending signals that the organization would need to do more if he was going to reach for a pen. Then, like now, the Bucks were charting a path forward after digesting a devastating playoff defeat at the hands of the Heat.
Holiday’s arrival was a game-changer on that front, with the move convincing Antetokounmpo that Horst, his staff, and Lasry were willing to do whatever it took to win it all. The five-year, $228 million deal that Antetokounmpo is currently playing on was signed a month later.
If the Bucks have their way, this Lillard deal will send them down that familiar path. More Giannis extensions. More titles. More champagne flowing in that locker room where the covert deal went down.
“It’s a beginning,” Antetokounmpo said with a smile.
(Top photo of Damian Lillard and Giannis Antetokounmpo: Photo by Juan Ocampo / NBAE via Getty Images)
