The DISASTER Damian Lillard Trade, 2 Years Later…

The DISASTER Damian Lillard Trade, 2 Years Later…

In the 2023 NBA offseason, we got a massive, pretty out of nowhere trade. The Milwaukee Bucks shocked the league by being the team that traded for Damen Lillard, who had requested a trade from the Trailblazers that off season. And unfortunately for the Bucks, as we look back on the deal now, it has been a complete disaster. So, let me take you back to the 2023 offseason. Damen Lillard, after a long career in Portland, has decided it is time for him to leave, and he has requested a trade. And the series of events leading up to his trade request were certainly interesting. He wanted the Blazers to improve the roster essentially to prove to him that he should stay despite the fact that he signed a giant contract extension the prior offseason. He was looking at other opportunities. And the Blazers were well set up to improve the roster because they had the third overall pick in the draft. Ultimately, they used that pick on Scoot Henderson, but reportedly they kind of maybe looked at trading that third overall pick for somebody, didn’t like the value they were going to get in return. And their decision to not trade the third overall pick to keep Scoot Henderson ultimately is what forces Dame essentially to request a trade from the team. Despite the fact they had invested in the roster in ways like giving Jeremy Grant a giant contract like a day or two before he requested a trade, it just wasn’t enough. Dame decided it was best for him to go elsewhere because he wanted to try and win and win a title. And he put some teams on his list. We had the Clippers, the Sixers, Miami, and at the time of the trade request and really throughout the entire trade process, it was just kind of assumed that Miami was ultimately going to be Damen Lillard’s destination. So, the trade process begins and Portland and Miami are having conversations and Portland just isn’t all that interested in what the Heat have to offer. One, they’re a little bit annoyed that Dame is trying to force himself so directly to one team because that is lowering his value around the league because despite the fact that he just signed a giant new contract and it’s not like he was going to be a free agent anytime soon, teams didn’t want to trade for an unhappy 32-year-old owed a bunch of money, Damen Lillard. So, they wanted to make sure he was happy to be there. And at the beginning of the trade process, he basically made it clear that Miami was the only place that he would be happy. Now, having said that, Portland would have been more than happy to trade him to Miami if they actually liked the trade offers they were getting. The problem was they weren’t a huge fan of the focal point of those offers, Tyler Herro. They just weren’t all that interested in his value, whether it be to them or to other teams around the league to try and flip him. And two weeks into the trade process, things are just not going well. And so, his agent puts out this really weird statement essentially saying, “Don’t trade for Damen Lillard.” which is just another effort to scare teams away and basically force the Blazers to just settle for whatever the Heat were offering at the time. The Blazers tried to find a way for other teams around the league like the Nets to take on Tyler Herro so they could get more assets in the deal. They tried to make the Heat thing work despite being annoyed, but they just weren’t impressed by the trade package that the Heat were willing to offer in exchange for Damen Lillard. So, the Heat increased their offer. And at the end of the day, it seemed like the final offer from Miami was Tyler Herro, two first round picks, some contracts, and maybe Nicole, but that’s uncertain. And at that point, the Blazers look at that offer and say, “It’s just not good enough. We understand that Dame wants to go to Miami, but this is not what we want in return to do the best thing for our franchise in the long term.” So, out of nowhere, the Milwaukee Bucks come out as a suitor. Dame says he’s okay going there, and they find a way to make a deal. The Bucks get Damen Lillard. Suns get Grayson Allen, Ysef Nerkish, Nir Little, and Keon Johnson. And the Blazers get Drew Holiday, DeAndre Aton, Tammani Kamura. Three Bucks picks, two swaps, and a pick in exchange for Damen Lillard. Now, not that long after, Drew Holiday is traded to Boston in exchange for Malcolm Brogden, Robert Williams, a 2024 first and a 2029 first. And then they use all those assets basically to get Denny Avida at the time of the draft. So the end return for Damen Lillard for Portland was Robert Williams, Denny Avida, DeAndre and Tammani Kamara and those picks that I mentioned earlier. And the craziest part of all this, really the legacy of the deal is that the two focal points of the trade, DeAndre and Damen Lillard were straight up waved or bought out by their new teams 2 years after the trade. But before we go too far here, let’s go back to the Bucks rationale and reasoning for making the Dame trade in the first place because they really weren’t that mentioned throughout the process. It was pretty much just assumed Miami was going to end up with him eventually before the Bucks really came out of nowhere. Now, they have a history of making these kinds of moves in an effort to keep Giannis happy. They’ve always been nervous about Giannis potentially leaving. And at the time that they made the Dame trade, they’d won just one playoff series since winning the 2021 title. and they had just fired their coach, so they really needed to make a big move. Now, unfortunately for them, that stuff that I just said about them only winning one playoff series since 2021 is still true even 2 years after making the Dame trade. But like I said, it’s not uncommon for the Bucks to make these kinds of moves to try and keep Giannis happy, to try and keep the team competitive. Famously, they traded for Drew Holiday when it looked like Giannis might leave and a year later, they won the title. And then of course just the concept of waving and stretching Damen Lillard’s contract in order to bring in Miles Turner of course was another example of a desperate move by the Bucks to try and keep Giannis happy. In that desperation they thought that the offensive upgrade from Drew to Damen Lillard would be really really impactful for them. Drew had had some really tough postseasons offensively the prior few seasons and they felt like they just needed to shake it up and most people at the time were excited about the move and what it would mean for Milwaukeee’s offense. The problem was it just never fully worked out with the Bucks. The Giannis Dame twoman game was good, but it was never really great. And that was really the main goal of the trade was to unlock Giannis more as a screener and have this really dynamic onball creator that they’ve never really had. It was Drew Holiday who’s not a great onball creator. Chris Middleton, who’s fine, but not on Dame’s level. And that connection, for whatever reason, just never really came together. And Dame’s spacing was absolutely helpful, but it just never quite reached the same levels of like, oh my gosh, Damen Lillard’s taking over this game. He’s made 10 threes all of a sudden that at times he got to in Portland. And defensively, they of course just weren’t the same, which everybody knew that that would be the case when you’re getting rid of Drew Holiday in place of Damen Lillard. It’s worth pointing out that all this stuff isn’t necessarily 100% on the Dame trade, by the way, because there was this weird coaching situation at the time. They they fire Coach Bud, bring in Adrien Griffin, he coaches like 40ome games. They bring in Doc Rivers in the middle of the year. So them being bad defensively isn’t just because they got rid of Drew and brought in name. But pretty quickly in year one, partially because of the coaching stuff, but then also because the name trade, there were questions about whether or not this was a good idea for the Bucks and whether or not they actually got better. Not to mention the fact that they were concerned about the gigantic contract that Damen Liller was on. This was kind of early on in the oh there’s going to be a new CBA. There’s going to be a second apron. We’re going to be concerned about spending. there’s going to be all these restrictions in terms of roster management when you spend so much money. And quickly the Dame contract became a main point of conversation in that he signed a new deal in 2022, the year prior to requesting the trade with the Blazers. He was already in his early 30s and he was going to be making between 45 to $55 million for the next couple of seasons in Milwaukee. And early in year one, there were concerns on the floor as well that this just wasn’t a good move for the Bucks. Dame was an all-star. He played 73 games, but he just never quite looked comfortable. Then as they go into the postseason, he did have some really big games in their first round series as Giannis and others were hurt. But then Dame himself got hurt. He played just four games and they lose in the first round. But it’s just year one. And the thinking at the time was, okay, that was a weird year. Dame himself said that he wasn’t really working out as much as he normally would that summer because he was worried about the trade requests and didn’t want to get hurt and then possibly not be able to get traded. There was the weird coaching situation where they’re bringing in Doc Rivers out of the broadcast booth in the middle of the season to coach the team. And they still won 49 games and could have done even more in the postseason had it not been for injury. So, they decide, okay, let’s just run it back. And in year two, Dame did look more comfortable, but he only played in 58 games. He made the All-Star team, but has a blood clot issue late in the year. And most people, myself included, just kind of assumed that Damen Lillard would be out for the season once that came up. But somehow he was able to come back early from that blood clot issue. He’s ready for round one of the playoffs and tears his Achilles in their first round series. And that is the final devastating blow that leads directly to the Bucks just cutting Damen Lillard. After two seasons, the Bucks had zero 50 win seasons, zero playoff series wins, and the core of the team had really barely played together in the postseason and then Dame was just gone. They took their big swing and they missed. But that isn’t the only side of this trade because of course Portland is involved here as well. The thought process at the time as we go back again to when the Dame trade was actually made was that the Blazers really wanted DeAndre Aton as part of the deal for whatever reason and the Bucks offer was just better than Miami because they thought that they could flip Drew Holiday for assets while they didn’t know if they could do that with Tyler Hero. And really at the end of the day the Portland trade return doesn’t look all that great for a player of Damen Lillard’s name notoriety. Eighton really wasn’t good for them and they bought him out after just two seasons and they’ve continued to invest at the center spot. So, it’s not like they’ve really solved that issue. Holiday ultimately got them. Denny who has been really good for them but isn’t like a franchise changing player. Tammani Kamura is a really good defender and then obviously the picks are kind of TVD. They’re so far out in the future still that they definitely could be really good because Giannis could be gone but we don’t really know how to value those yet. So, it’s not terrible, but trading Dame for basically two years of Aiden, Denny, Kamara, one pick and two pick swaps is just kind of eh it’s just kind of not great. Now, granted, the picks could be great and Dame was owed a ton of money and was 32 years old at the time and clearly his destination in the Miami of it all really played a factor in how much value Portland was going to be able to get out of Dame in the first place. It’s still a win for Portland, absolutely, but not necessarily a franchisechanging move as of right now. And really, I think the legacy of this deal is going to be what it did for Milwaukee. They gave up a bunch of assets that they could have used in other trades. Really, nobody expected Dame to just not be on the team two years later. And if that was the case, it would be because it just didn’t go well, and they would be able to flip him to Miami anyway, and that’s just where he wanted to go. Ultimately, having to just wave and stretch his contract after just two seasons after a devastating Achilles injury is an absolute disaster of a trade. Now, Milwaukee could not have anticipated the Achilles injury, and had that not happened, they would not have waved and stretched Dne’s contract. They would have just kept him for the next two years of the deal and tried to convince Giannis to stay in other ways. But even without the injury, it’s very easy to say that this was just a mistake by the Bucks. The calculation that they made on improving their offense, becoming more dynamic offensively, it just never came together. And ultimately, Drew Holidayiday ends up in Boston and becomes this NBA champion with the Celtics and makes them this super team that ultimately they break apart. But not only did they not improve their own team, but they made their biggest competitor in the Eastern Conference even better even though just for two seasons because Holiday ends up in Boston. I think if you really gave Truth Serum to members of the Milwaukee front office, they would say they absolutely regret the deal. And that might have been the case even without him getting hurt and having to wave and stretch the contract. But this is one of the bigger disaster trades that we’ve seen in the NBA really over the last decade or so.

In the 2023 NBA offseason we got a MASSIVE out of nowhere trade – the Milaukee Bucks shocked the league by being the team that traded for Damian Lillard, who had requested a trade for the Trailblazers that offseason… and unfortunately for the Bucks – the trade has been a complete disaster.

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