Trade Analysis: Damian Lillard goes to Milwaukee in three-team blockbuster

In a stunner of a deal, the Milwaukee Bucks acquired Damian Lillard in a three team trade with Portland and Phoenix. 

The full reported trade:

Milwaukee gets: Lillard

Portland gets: Jrue Holiday, Deandre Ayton, Toumani Camana, Milwaukee’s 2029 first round pick, and pick swaps in 2028 and 2030. All picks and swaps are unprotected. 

Phoenix gets: Jusuf Nurkic, Grayson Allen, Nassir Little, and Keyon Johnson. 

Karalis’ analysis: Giannis Antetokounmpo was very loud and very clear about his feelings this summer. He’ll stay in Milwaukee as long as they're serious about being a contender. 

Well, they're serious. 

They paid a decent price for Lillard, giving up their best defensive player in Holiday and picks that could come in a post-Giannis rebuilding era, or at least on the downside of his career (he’ll be 33, 34, and 35 when the three traded picks are made). 

Those picks could be very valuable, but Milwaukee clearly hopes the afterglow of multiple championships will comfort everyone in the Deer District long enough to excuse the extended rebuild. They could also restock their cupboards by trading Antetokounmpo at the tail end of his greatness just like Portland did with Lillard. 

But that's a question that will be answered later. For now, the Bucks have added one of the league’s most potent scorers and clutch shooters. For all the talk about how old Lillard is and how smaller guards age out faster than NFL running backs after 30, this is also very clearly the best team Lillard has been on, and being flanked by Antetokounmpo and Khris Middleton will ease a lot of the workload Lillard has been carrying. He won’t have to play 36 minutes a game and be the singular focal point of opposing defenses. 

No, he’s not going to South Beach, and we’ll see if that's an issue for him, but this is clearly a much better situation for him. 

As far as a Boston matchup is concerned, Lillard going to Milwaukee certainly puts pressure on Boston to field a competent defensive team. Holiday and Allen had both struggled in the playoffs, with Allen especially being exploited by Boston. Lillard will still be a weak point to attack defensively, but he can get whatever points he gives up back in a hurry. 

Milwaukee’s defense certainly took a hit in this deal, but they’ve generally been pretty creative in getting the job done on that end. It’ll be a hell of a task for first-year coach Adrian Griffin to figure this out, but I don’t think he’s going to nuke a lot of what’s worked for them with this personnel in the past. 

The biggest advantage Boston has over Milwaukee still exists: the ability to play Brook Lopez off the floor. They can still spread the Bucks out and attack them at the rim, and without Holiday there to hound the ball handlers, the attack will become a bit easier. 

That could force the Bucks into a lot more zone, which has obviously been a little too effective against the Celtics. The addition of Kristaps Porzingis should be able to neutralize that some, as would some better shooting all around from Jayson Tatum and Jaylen Brown, who both had some down shooting seasons. 

Porzingis’ defense will help Boston get more aggressive against everyone’s perimeter players, not just Lillard and the Bucks. If Porzingis and Robert Williams can keep Giannis away from the rim, they’ll probably be able to defend Milwaukee effectively. 

It won’t be easy, but then again facing the Bucks never is. Adding Lillard changes how they’ll play offensively, and it will open things up for Antetokounmpo and Middleton. Milwaukee will challenge Boston for the top seed, but I still like the matchup for Boston. 

Phoenix, meanwhile, finally moves on from Ayton. They're taking on the more specialized Nurkic, who will provide more rebounding and scoring around the rim than Ayton, who likes to hover around the midrange. 

Basically, the Suns are getting Ayton out of Devin Booker, Kevin Durant, and Bradley Beal’s way so they can cook. The move also gives them some needed depth with Allen and Little. They can spread the floor for the primary scorers, the scorers can shoot, and Nurkic can rebound. All of the headlines will be about Lillard, but Phoenix did alright in this deal. 

Portland is expected to immediately shop Holiday, which means Miami could still be in the mix to get a good point guard that can help them. In a weird way, the Heat missing out on Lillard might be a blessing in disguise because Holiday fits Miami’s ethos better than Lillard does. 

The Heat are built on toughness and defense leading to offense. Holiday won’t be the potent, 30 ppg scorer that Lillard is, but he will be an All-Defensive Team and Defensive Player of the Year candidate who shot 39.5% from deep over three seasons in Milwaukee. 

Holiday has no place in Portland and the Heat have had recent talks with Portland, so it makes sense for the Blazers to turn around and quickly flip him there. If he doesn’t end up in Portland, I can also see the Sixers making a run at him. 

The Blazers are in full tear-down mode, so Holiday might not make it to media day in Portland. I don’t know what their plans are for Ayton, but I wouldn’t be shocked if he’s shopped, too. 

The bottom line here: Milwaukee got a lot better offensively, and they’ll put on an even stronger challenge for the top seed, In a head-to-head matchup, I still like how things line up for the Celtics, but I’m a little concerned that Holiday could end up on a rival as well, which wouldn’t be great for the Celtics.