Jrue Holiday felt “shocked” by Bucks trade for Damian Lillard, joining Celtics | Draymond Green Show

In this episode of the Draymond Green Show, host Draymond Green interviews NBA guard Jrue Holiday about his sudden trade from the Milwaukee Bucks to the Boston Celtics as part of the Damian Lillard deal. Holiday recounts receiving the news while napping, the frantic 24‑hour window to arrange his family’s move, and his feelings of being blindsided despite his championship experience. He discusses the defensive void his departure creates for the Bucks, especially the loss of his ability to funnel opponents into Brook Lopez’s rim‑protecting drop, and reflects on the trade’s impact on Milwaukee’s roster. Holiday explains why he chose Boston over other suitors, citing the Celtics’ championship culture, the team’s need for a defensive guard, and the appeal of playing for a storied franchise. The conversation also touches on the rivalry between the Celtics and the Bucks, Holiday’s personal ties to Los Angeles and the Lakers, and how he navigates fan expectations and pressure in Boston. Throughout, both Green and occasional commentator Colin Cowherd probe Holiday’s reactions, his relationship with former teammates, and the broader strategic implications of the trade for both clubs.
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What's up everybody? Welcome to the Draymond Green Show YouTube channel. Make sure you hit that subscribe button. Make sure you like the post that you love, but you can get everything the Draymond Green Show right on our YouTube channel. So make sure you subscribe, check that out. Thank you. Take me through the process this time though. This time around there's a bunch of reporting going on that Damian Lillard is gonna get traded. No one knows where. He keeps saying Miami, or people keep saying Miami's number one choice or the Knicks. Bucks isn't even a conversation. And then all like, how soon with that did you know that you were getting traded?
Yeah, I was, I mean, so I, through the week, you know, in the off season, you go in, I'm already in Milwaukee 'cause my kids go to school there and they started school and we're there. We working out. I mean, most of the team is there working out. Monday, Tuesday, I work out. I take Wednesday off, kind of do my own thing, recovery day. And then Thursday, Friday, I work out. And then the weekends, I kind of do my own thing, me and my wife. Well, Wednesday was my day off, and I'm taking a nap. And I'm taking a nap, and I got my watch on, my Apple Watch on, and I see the text. I see a call from the GM, and I'm like— Whoa. I'll call him back. Like, I'm deep in this nap too, I'm saying. It's a good one. And then 2 seconds later, my agent calls me. I'm like, all right. So I pick up his call. He's like, you talk to him? I'm like, nah, bro, I'm sleeping. He's like, well, you just got traded, so you should probably call him back. And then I ended up looking at my phone. He ended up texting me. Um, everything that was happening, like, yeah, we trade you here, here. And then I ended up calling him and he ended up saying like, yeah, we traded you for Damian Lillard. So I also had no clue, like, just like the world had no clue. I also had no clue. Uh, he did tell me, I think, before it broke on Twitter and all that. Um, the world kind of knew, but I think for me it was just a shock because I had no clue, like out the blue. And I think a part of me thinking like, maybe I felt like I— not that I was untouchable, but maybe I had done enough to at least let me know 24 hours in advance, not 5 minutes in advance. And maybe I'm asking for too much, I don't know. But it's kind of like— Mm-hmm. I mean, we won, I won there. You know what I'm saying? We won there, so.
How many championships in Bucks history? Yeah, you ain't asking for too much.
50-year span. But again, I'm not upset with it. I'm not upset with it. It was just more of a shock. Like, I didn't think that if I was gonna get traded, I thought, I would at least know in advance. I could prepare my family, I could prepare my kid. Like, we had a life there, and like I said, my kids were already in school. Um, and then that next Sunday, or that next Monday, was training camp.
Wow.
So it, like, it wasn't like in the middle of the summer or the middle of the offseason. Like, no, we had 4 days. So I, I have to figure out how to move my family I gotta figure out, for one, I gotta figure out where I'm going.
Yes.
'Cause I didn't end up staying in Portland, and that also took a minute too. So I'm in limbo for 3 days, like not really knowing what's going on. And then when it all kind of came together at the end, I mean, I really thank God for Portland and Chauncey and the GM there, 'cause they really, like, did, did good by me, um, just really asking me and talking to me where I wanted to go and, uh, if I was on the same timeline as them and all that. And they did it. I mean, I love them for that. But, um, it was just such a shock. And then being thrown into another system that I had no clue about. But being traded 4 days ago and then having just the Fly there and go straight into training camp was crazy.
Did you get a chance to talk to Giannis, Dame, anybody?
Like, you know what I'm saying? I talked to Dame. I was like, "Hey bro, you gonna love it here." I think like, 'cause honestly, just like everybody else think, I thought Dame was a good fit with Giannis. Like how they play together, the pick and roll, adding K-Mid to that. And you got, you got Brook. Obviously stretching the floor. You got Bobby stretching the floor and being a bully in the paint. I thought it was a good fit for him. So I ain't had no hate or anything. I talked to Giannis a little bit, but the first person that called me was Chris. And he came to the house and we had a deep conversation. We had a good conversation, so.
That's—
Yeah, yeah, K-Man, my boy. So it was— It was good to kind of talk it through with him because honestly, I think a lot of them were just as shocked as I was. Like, I don't think anybody knew. I think they kind of kept it close to the chest for the most part. Again, I don't know who knows, who knew like the whole story and who didn't. So I can't speak on all that. But like, I know, I know a lot of them, they just kept it close because if it did get out, I feel—
Mm-hmm.
I, yeah, again, I don't know. For me, it's like I'm a grown man and if you tell me that like I'm possibly gonna get traded, I'm gonna be like, all right. Yeah.
I think that's a tough thing to do though for a GM, for being who you are and what you meant to that team. And like, you have to play well for that team to win. If they like, yo, you may get traded and then all of a sudden you don't, that could be tough because like, All right, well trade me then. Like, get me outta here now. So I get that from a certain extent, but this isn't a normal situation. This isn't like some guy that just played here and now we just moving on because it didn't work. Like we just won a championship. We're within 2 years of winning a championship.
Yeah.
And we still have championship aspirations. It's pulling me outta the puzzle. Gonna help better that championship? I personally don't think so. Not that Dame isn't great, but just for what you meant to that team. Like that team took a big hit defensively all year because of the way— people don't understand the way Giannis and Brook play in the drop. That only works in today NBA if you have a guard that, A, doesn't get screened and chases over the ball like a hawk. Like he chases over the screen like a hawk. And with you chasing over the screens, they can sit in that drop and you are good enough to funnel them to the drop. All of a sudden you remove that and you don't have anyone to do that. And Grayson Allen was gone, who I also thought was y'all second best perimeter defender.
Bro.
Like defense took a huge hit.
Bro, when I tell people, during that time because me and Grayson, um, just ironically, me and Grayson didn't go in the same day. The day that we got traded, Grayson also didn't go in that day, which I don't know. Yeah, I don't know why, but Grayson was killing this offseason. Grayson put in work and he was killing. I'm like, he is the best player on the court this offseason. So I think all of it kind of Like, looking back at it, I'm like, man, it was— I do think defensively it was a big, um, it hurt him a lot. But, you know, trades can be made and you can try to find defense and, and do all that. But I agree with you, I think that I was kind of perfectly put, or I fit perfectly in funneling guys to Brook, who I think last year had career-high blocks. Obviously you see what Giannis does blocking shots and stuff. So I was like, I was meant for that. But—
Yeah, for sure. Brook was mentioned as defensive, possibly defense player of the year last year.
Yeah.
And I don't remember nobody ever mentioning Brook for nobody's defensive player of the year. So that does definitely show your impact. But did you, so you pretty much chose to go to the Celtics, like the Blazers kind of gave you that right to just kind of pick where you wanted to go?
Yeah, there were other teams, teams that I wanted to, um, they were one of the teams that I wanted to, uh, try to go to. Obviously they have pieces. Um, I think something happened with Brock— uh, with Malcolm earlier where—
Yeah.
He didn't go to the Clippers, so I think he was maybe looking to go somewhere else. And, um, he was definitely one of the teams, but I wanted to go to a contender. I mean, there's a few of them out there where I felt like I can make my impact. It was like There's the Clippers at the time, there's Miami, there's the Celtics. And I think maybe those are the, like, the big 3, the ones that I felt like, you know what, if I go there, I could really, really do something. And, you know, after you get traded, sometimes you kind of question not your abilities, but like sometimes your confidence. Like, am I as good as I think I am? Because like, I can just be traded for nothing or not even know about it.
Mm-hmm.
But to see so many people kind of text me and be like, dang, like I didn't see that coming. Getting those text messages, man, I'm like, you know what? Like, yeah, I can still hoop.
It ain't over.
That part. You know what I mean? I'm still nice. So it was cool to kind of have that feedback.
But what was your reaction like initially? Like y'all just finished playing the Celtics and back and forth for the last few years. And you know, that thing has grown into a rivalry. What was your reaction to that? Was it more like, damn, I don't know if I wanna go, or because of the way they traded you, it's just like, no, I actually wanna go there and get back at them.
It was more like, yeah, I wanna go there and win. It wasn't necessarily to get back at them because like I told you about my first trade experience, um, it's happened to me before. I've been traded without knowing. I've been traded for, um, I mean, for whatever reason, and it just got like, like 30-second call, I'm somewhere else. So, and I still love the guys on the team, you know what I'm saying? But I also want to beat them. Yeah, you know what I'm saying? I also want to beat them. So it's not like in spite— I didn't go there in spite of them. I went there because like that's my best chance of winning. And again, it ended up working out to where I feel like the Celtics equally wanted me too. Like, it wasn't just me—
They needed you.
Right, it wasn't just me going after them. Like, they also pursued me too. So I think it was, that definitely worked. But it wasn't, I wasn't going there like, yeah, I'm gonna get back at the Bucks. It was like, well, I'm gonna go there and win. If we gotta go through the Bucks, then we going through them. Absolutely.
And I, you know, I can appreciate that and I love it because see what people and you know, people get mixed up all the time and they forget these time of these events. Marcus Smart was already traded. The Celtics didn't have a point guard going into the season. Like again, 4 days away from training camp, they didn't have a point guard. This Damian Lillard trade actually made Brad look like a genius. Because now all of a sudden you end up in Boston. They traded Marcus Smart not knowing that that was happening.
Not knowing.
It was almost like a panic. Like, oh man, we can't win. All right, the money getting up there. JB money kicking in. We know we about to pay JT. We might as well start getting off some stuff now. It was almost like a panic and like them letting go of the rope, how I viewed it. And then all of a sudden you pop up. And everybody's like, oh, Drew's in Portland, but Drew said he not staying in Portland, he's available. And they come up on you and it, and I mean, it's changed everything.
It's been fun, bro. I'm not gonna lie. It's been fun. The culture here in Boston, what it means to win, the history that it has. Like me being from LA, growing up a Laker fan.
Facts.
That was probably the weirdest part for me.
Ah.
Like being in that green, being a Celtic, knowing that I was gonna sign to be a Celtic was like, am I portraying my roots? Like where I came from? Obviously growing up a Kobe fan, I thought I was supposed to be 6'8" and be like Magic. Like, am I betraying where I came from? 'Cause all my family to this day, still Laker fans.
Mm-hmm, absolutely.
Like I got family that came to the game in Boston with Laker stuff on. I'm like, you got me messed up.
Crazy.
Thinking that you gonna come and watch this game with a LeBron jersey on. Like, what is wrong with you? Right, right. I got, like, I got family from LA who still came to the game with Lakers stuff. I'm like, yeah, that's crazy to me. But that's the rivalry. That's like the history behind it. But being in that Celtic green, bro, like, it, like the pressure, like it's different. I mean, you could probably attest to it. Being on top for so long, or even them like kind of doubting you, like you can't win. Like all they talk about here is winning. And the only thing that is important is winning. And I'm like, man, I'm here for it, bro. Like I'm here for the ride. So I'm excited. I'm excited to be here.
Now that's crazy. But that's also a different type of pressure. Like even for us, when we came in here, this, like we made it to the playoffs my rookie year. We poured water on each other. Like Mark Jackson don't, I don't do liquor. Like we had a water celebration, not champagne. But because that was like, I mean, the biggest moment was the "We Believe" season.
Yeah.
And like since '75, that was the biggest moment in history was the "We Believe," winning a first round playoff series. So we didn't necessarily have like pressure to win at the level that we've won at because you just couldn't compare it to anything. But you saying, Y'all feel that pressure. Like they make sure y'all feel it and know like, no, we gotta win championship. That's it here in Boston.
I mean, you played in the Garden. You know what the fans are like. Yeah, it was crazy. You know how crazy they— Right. It's like, it's live or die. Like they Celtics green all the way. So I think kind of being in a position and bro, big, like big props and big ups to JT and JB because I feel like they, holster most of the pressure. Like a lot of it is on them because they've been together for so long and kind of have gone through this where they've been to the conference finals and they've been to the finals and all that so many years in a row. And even what they did last year, like almost coming back from down 0-3 against the Heat.
Yeah.
I think that, Playing with them and seeing like, now that I'm on this side and seeing like the pressure that they go through and how they handle themselves is like, is ultimate professional. Like I don't think a lot of people would be able to do what they do.
Now that's incredible. And they carry it well because it doesn't come off that way. Like obviously we all hear the talking heads on ESPN or on this show or, Like, but to be feeling that pressure at home, you know what I'm saying? Like to be feeling that pressure from your fans, to like, that's a different type of thing to handle because when it, at any moment, like you hit a rough patch.
Yeah.
Like they, you should trade this person, you should trade that person.
Right.
And yet you still gotta try to keep that same love for this fan base because you're one in the same in a sense you're trying to do the same. For sure. That's a tough thing to do. And I don't think people realize how much that takes and how much that says about those two and just where they are in their maturity.
Yeah, nah, it's, and I saw that from day one, bro. Like, and you know JT and I mean, you know JB too, but you know JT like super cool and calm. It don't seem like anything mess with him and all that. But I know like, again, just being here and seeing that type of pressure, bro, I'm like, man, like, I really admire it. Like, and they do it with such a grace. And just how they handle themselves is like way wiser or like wise beyond their years. So it's been, it's been cool to kind of see that.
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