A timeline from 2018-23: How and why the Milwaukee Bucks traded for Damian Lillard

In a few preseason possessions of the Giannis Antetokounmpo-Damian Lillard pick-and-roll combination for the Milwaukee Bucks, the Los Angeles Lakers and Oklahoma City elected to focus on Lillard rather than the two-time league MVP running free to the rim. Antetokounmpo said after the Lakers game he was never that open. Lillard seemed unsurprised, saying he’s seen traps and double teams his entire career.

Khris Middleton joined them on the court for a few minutes in the preseason finale against Memphis, and suddenly the 47x50 foot half court looked far bigger.

On the micro level, this is why the Bucks traded for Lillard. Defenses will have to decide which of the two NBA all-time top-75 players they leave to single cover. They’ll have to decide if Middleton, a three-time all-star, is worth leaving open altogether. The macro, of course, is that the Bucks traded for Lillard to win the 2023-24 NBA championship and perhaps more.

But as with anything, there’s always a bit more behind how it all got this point.

Here a look at the long timeline that eventually led Lillard to Milwaukee.

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As an organization, the Milwaukee Bucks had checked in on the availability of Damian Lillard over the last few seasons. But as for Lillard and Giannis Antetokounmpo, their relationship began with an intermediary.

July, 2018: The Bucks sign 25-year-old Pat Connaughton, a free agent who spent the first three years of his career coming off the bench in Portland.

Lillard: If anything that made a difference, it was when Pat came here. Me and Pat was real close in Portland. He was my rook. He came out, and I be like hey, so Giannis going to Portland and you come back with him. Then he was like, you know, Giannis said you come to Milwaukee. You come here. It was like a back and forth like that.

Connaughton: The interesting part was the personal relationships and friendships I’ve built with all the teammates that I’ve had. They want to win at the highest level and I think they each saw that their games complement each other. I think they each saw that they’re family-oriented guys, they’re fathers first. So, they each kind of reached out to me about it very early on. I think it was my first year, it was 2018-19. ... They wanted to play with each other some day. Obviously at the time Dame had an idea of Giannis going to Portland and Giannis had no interest in going to Portland. And Giannis had an idea of Dame coming to Milwaukee and Dame had no interest in coming to Milwaukee at the time.

March 7, 2021: Antetokounmpo and Lillard were on opposing all-star teams in 2019 and 2020 but were teammates on LeBron James’ 2021 all-star squad. It was that “bubble” all-star game in Atlanta where the two stars got to know each other a little bit.

Lillard: It was kind of weird because you couldn’t leave the hotel. I remember that year on the bus to the arena from the hotel it was me, Giannis and “Joker” (Denver star Nikola Jokić). ... I was sitting on this side and I feel like “Joker” was in front of me in the seat and Giannis was the row next to me and we were having a three-way conversation. That was really the most dialogue we had in person like that. Then we got to the arena and before we went out on the court to do all the stuff, me, him and “Joker” was kind of carrying on our conversation in the hallway before we went on. And then (Dallas’) Luka (Dončić) came out. So it was all these foreign dudes and me, you know?

I don’t think that opened up no type of dialogue. I think it just gave me a better look, to hear him speak and how he thought. He gave me a better look at the person, you know what I mean? And I think the same for him. I probably at that point had more dialogue with (Thanasis) than I did with Giannis. We had always exchanged respect when he seen me and I seen him. That was it. I wouldn’t say it opened up dialogue.

But the interaction did create a lasting impression. The pair would playfully talk about playing together, but always with one saying the other should come to their respective city.

May 15, 2022: Lillard sends a post on X, then Twitter, that said he would pick Giannis as a running mate to go to the playoffs.

July 9, 2022: Lillard signs 2-year, $122 million extension through the 2026-27 season following a season in which played in 29 games and had abdominal surgery. He is the first player in the “maximum” contract era to extend his deal with multiple years already remaining.

Feb. 19, 2023: Antetokounmpo picks Lillard No. 1 in All-Star Game draft, over Jrue Holiday.

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April 13: Lillard tells ESPN he would have to make a decision on his future if the Blazers don’t make a full commitment to winning at a high level.

June 6: Lillard says he will request a trade, preferably to Miami or Brooklyn, if the Trail Blazers did not improve the roster.July 1: Lillard requests a trade, preferably to Miami.

July 6: Lillard’s agent Aaron Goodwin tells teams to not trade for Lillard, who would be unhappy other than in Miami.

Mid-to-late July: After the Las Vegas Summer League schedule ended on July 18 the Bucks engage in substantive talks with the Trail Blazers about acquiring Lillard.

July 28: The NBA sends a memo to all teams that players cannot dictate trade to a particular team.

Aug. 24: Antetokounmpo echoes past comments and says he wants to continue to see a championship commitment from the Bucks to sign an extension.

Sept. 12: Antetokounmpo reiterates those statements on his friend Ross Geiger’s podcast. Geiger is a former Bucks employee who has remained close with Antetokounmpo.

Antetokounmpo: We are judged in winning games, right? So I want to win. I’ve always wanted to win. I still want to win. And it’s always going to be like that. I want to be a part of a winning team and I feel like, I hope everyone feel that way, I do feel that way. The last couple of years, I see the commitment from the team they’ll do whatever they can to make this team a championship-level team, so I’m happy.

I’m happy to be able to wake up every single day, come to work and know that I have a chance to win a championship instead of just coming here and knowing that there’s no way we’re going to make the playoffs or we are going to be one of the worst teams in the NBA. Like, I don’t like that feeling. I like kind of looking forward to something bigger than me, greater than me. Every year that I wake up and every day that I'm going to wake up going forward and I’m going to be on the team I want to feel like I walk in here and I have a chance to win a championship.

Sept. 17: Aaron Goodwin calls Bucks assistant general manager Milt Newton to say Lillard would be open to coming to Milwaukee. This was the nudge the Trail Blazers and Bucks needed to have more serious, one-to-one conversations.

Lillard: As he got into it, my agent called me and he was like, what about Milwaukee? Obviously Giannis, it’s public record that I’ve always mentioned if I had to team up with one person it would be him. So when we talked about it I told him I would definitely be interested in that, obviously. He was just like, OK, and I could tell he kind of put it in his back pocket. Obviously in these situations you never control completely how things end up or where you end up going. So, it came about and it was an option and it was like press play, why not? Why pass up on that type of opportunity? So, it as something that came up I would say two weeks ago and I was interested in that for sure.

But, there were parameters. A league source with knowledge of the initial discussions noted the Bucks entire roster was not for the taking.

Sept. 24: Trade discussions between the Bucks and Trail Blazers substantially kick up.

Sept. 27: The Bucks trade Jrue Holiday, a 2029 unprotected first-round pick and two first-round pick swaps to Portland for Damian Lillard. They also send Grayson Allen to Phoenix in a three-team deal.

Lillard told Bleacher Report he was informed of trade just after 1 p.m. CT.

Lillard: I was just kind of sitting there in my man cave. I didn't know what was really going to happen. I started to think like, man, it might get to training camp and I might just be sitting and waiting. And then I got that call from my agent and it was like, man, you’re getting traded to Milwaukee. And I had heard so many different things and it’s like, am I really getting traded? He’s like yeah, they traded you. And I could tell in the seriousness of his voice that it was real. He was like, I’ll let you sit with for a while. I’ll call you back, I’m going to settle some things and we’ll talk about it.

After we got off the phone, I sat there and I was like, I'm really moving on. It became reality for me. I kind of just started to think, my entire family is here. How am I going to pack everything up? I started to panic a little bit. It’s the first time. Then I wanted to let my family know, so I started walking around the house and nobody was there. Everybody was out doing something. I'm calling people and nobody's picking up the phone. I was like, man, any other time I'd be able to reach whoever I need to. So, I had to sit with it by myself for a while. So when that happened, I just went back to the man cave and I sat there, and that's when the calls started coming in. My friends, family members, like is it real? Is it true?

Then, I started to think about the team. It was like, who did I get traded for? Who’s going to be there?

The news broke at roughly 1:16 p.m.

Antetokounmpo: I was in the weight room. I was lifting weights and then, I don’t want to say who was next to me, somebody on the phone said. "Oh!" I don’t know what was going on. I always try to be locked in and finish my job, but I could hear (whispering). I turn and say, "What’s going on?" And they said nothing to me, they just showed me (pantomimes holding out a phone). ...

It’s hard. I went to the locker room and talk(ed) a little bit with Khris. Finish talk(ing) with Khris, came back up, finish my work because at the end of the day no matter what is going on I’ve got to finish my work, I have to finish what I started. Went back in and got back on the phone with Jrue, you know? Talked, kind of (to) hear where his head was. Talked a little bit, dropped the phone, did my recovery, went back home, and just spent two quiet days kind of reflecting and understanding what all the situation was.

Middleton: I just got done with a workout session. I would say it’s just mixed emotions. First, not knowing if it was really real or not because it came out the blue. Then it’s tough to see our guy go. What he did for our organization as he did for me as a person and my family. It was tough to have that conversation to see him go the other way. But to get somebody like Dame in, you gotta be excited or a guy like that.

Bobby Portis: So I was in a commercial shoot. I was chilling, I was dribbling the ball with some kids – there is a scene with some kids bout to come in – and everybody just stopped. I was like, "What’s going on?" They’re like, "Ohhhh! Ohhhh!" I’m like, "What’s going on, what happened?" They’re like, "We got Dame!" I’m like oh, fake news. Don’t believe everything you see on social media. They do all these jerseys, all the kids got these fake pages, they do jersey swaps, you see it every year, somebody with a new jersey. Then I see (ESPN) and I was like, oh, shit, it’s for real.

Horst: It’s unique and hopefully very impactful. You can’t get something without giving up something in this league and we all know and I think 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. It’s a great opportunity for this organization and we’re really excited about it.

Connaughton: It was just funny to see. The comment that I made that the three of us laughed about when this all came to fruition was being the middleman, being the messenger, being the guy that knew them both personally and professionally I said, "Hey look, I’m happy to play anywhere, just make sure I come along for the ride!" Right?! "I’m not saying we’re a Big Three – Khris Middleton can have that title – but at the end of the day just make sure I’m a part of it because I’m going to help you guys win in some capacity or another." And they both laughed and they both agreed.

Aside from the obvious on-court match, there was a significant off-court reason the Bucks had to do this deal either in the offseason, or by the February trade deadline: They would not be able to aggregate multiple salaries to acquire one player next summer.

As a second apron team heading into the summer of 2024-25, the Bucks would face stiff roster building penalties for the first time. While the new rules were not an overriding factor in making the move, it was taken into consideration by the Bucks front office and ownership.

More: Q&A with Bucks GM Jon Horst: On tax aprons, new ownership and Giannis' health

League source familiar with the Bucks salary cap situation: You can’t make the Lillard trade next year because you can’t aggregate two guys together to meet his contract – it’s literally illegal. "We gotta go do it," rather than "Let’s see how this year plays out and we’ll figure it out next summer." You can’t wait.

As much as these rules are meant to stifle these teams from super-duper overspending, if you’re already up there and you expect to win championships in the next couple of years, you might as well go now because you won’t be able to go later. In the long run, by 2028 and all the rules have been in place for five years and everybody’s had to comply with them, that’s when we’ll sort of start to see the rebalancing of all the max guys. But it’ll take some time to get there because the teams see it coming.

October: Lillard is introduced at Bucks media day on Oct. 2 and the star duo play three preseason games together. The season opens Thursday night at Fiserv Forum against the Philadelphia 76ers.

Lillard: Obviously I’ve spent my entire career in Portland. Eleven years is a long time, so I’m extremely thankful for that organization, that city, the fans for giving me the kind of experience that I had. I don’t think it’s a secret how much I want to win. That’s who we got here today and I think they want to win as equally as bad as I do, and I couldn’t be more excited, I couldn’t be more thankful for this opportunity to be a part of this organization, to play alongside the best player in the league, it’s going to be fun.

Antetokounmpo: I feel like we are just the same people, just different size. He plays with a chip on his shoulder. He plays to win. He’s built from the same cloth. ...

Whenever I saw him, I admired his game. I loved how he plays the game. He’s so effortless. ... We haven’t worked out together or anything or hung out or gone to dinners and stuff, but I’d always see him in the All-Star Game with his family, and he’s a guy, like one of the best in the league, one of the best point guards in the league probably, if not top one, top two, shooters in the league, incredible. He’s a guy that you always if you had the chance to play with, you would always love to play with, but I never imagined he was going to be here in Milwaukee and he was going to be playing with the team this year.

I’m excited for him. I’m happy for him. And hopefully we can have a great season and we can both stay healthy and go do what we do.

This article originally appeared on Milwaukee Journal Sentinel: How and why the Milwaukee Bucks traded for Damian Lillard