Giannis Antetokounmpo and Damian Lillard of the Milwaukee Bucks

Breaking down the Damian Lillard & Jrue Holiday trades for each team

On the afternoon of September 27, 2023, the prayers of Damian Lillard were answered. Adrian Wojnarowski broke the news on Twitter, announcing Lillard to the Milwaukee Bucks, in a three-team deal involving the Bucks, the Portland Trail Blazers, and the Phoenix Suns. Here is the full trade:

Milwaukee receives: Damian Lillard

Portland receives: Jrue Holiday, Deandre Ayton, Toumani Camara, 2029 unprotected first-round pick (Milwaukee), rights to swap Milwaukee’s 2028 and 2030 first-round picks

Phoenix receives: Jusuf Nurkic, Grayson Allen, Nassir Little, Keon Johnson

In a saga we thought would never end, Dame’s chapter in Portland has come to a close. Now, the 33-year-old looks to make a long-awaited push for a title, and we’re talking about a REAL push. The Trail Blazers never surrounded Dame with real talent to truly contend, so this is really the first time he can say his team has a very real expectation to win it all.

Shortly after Jrue Holiday was exiled to Portland, he found his way back on a contending team, being traded to the Boston Celtics for Malcolm Brogdon, Robert Williams III, first-round picks in 2024 (via Golden State), 2029 (unprotected via Milwaukee previously used in Lillard trade), and 2029 (unprotected via Boston).

In order to truly appreciate this trade, the gains and losses for each team must be broken down to see how it will affect each franchise involved:

Milwaukee Bucks

Bucks Gain: Even More Offense

Milwaukee was a clear favorite to make it out of the East in the days before Jrue Holiday made his way back to a contender. Yes, he was a great point guard for the Bucks for three seasons, but Damian Lillard provides an elite offensive presence that fits perfectly with Giannis Antetokounmpo. A top-five, maybe even top-three point guard joining forces with the best power forward in the game right now? If Khris Middleton can become consistent and healthy again for the Bucks, they’re goal will undoubtedly be to win the championship for the second time in four seasons.

Spacing is the key strength for the Bucks. Dame is a perimeter threat, and while he can slash at the rim, Giannis will take care of that job, with Middleton as a lethal catch-and-shoot option. Brook Lopez can also space the floor, and with other shooters like Jae Crowder, Pat Connaughton, and more, Adrian Griffin’s offense is going to be scary.

Bucks Lose: Elite Perimeter Defense

The key for this team to get back to the top is to maintain the elite perimeter defense that Holiday once provided. That’ll be tough after losing Holiday AND Grayson Allen. Both starters last season provided Milwaukee with the fourth-highest defensive rating at 110.9.

Now, while their offensive production will surely boost, they need to hold down shooters, because they’re set in terms of big defenders. Giannis and Lopez are both stellar when it comes to blocking shots, but Lillard and Middleton aren’t as defensively efficient. They also need to figure out their starting shooting guard, which will likely either be Pat Connaughton or Malik Beasley. Again, while the offensive production from those guys is acceptable, the defense isn’t as prominent. They’ll have to decide how to add the prowess they once got from Holiday.

Portland Trail Blazers

Trail Blazers Gain: A Sense of Direction

Finally, Portland has started the rebuild. Essentially, the Blazers turned Damian Lillard and Jrue Holiday into Deandre Ayton, Toumani Camara, Malcolm Brogdon, Robert Williams III, and five first-round picks. That’s a really good haul for GM Joe Cronin.

Rookie Scoot Henderson will now take the reigns as the new franchise point guard, and if he and Shaedon Sharpe can resemble the one-two combo that Lillard and CJ McCollum once were, the franchise will be in good hands. They could even compete for a Play-In spot if all goes well.

Trail Blazers Lose: Their Franchise Star

Obviously, this is a tough blow for the fans in Portland, losing your long-time superstar and fan-favorite in Damian Lillard, but it was about time. It’s not much of a loss when you realize that this was long overdue.

Phoenix Suns

Suns Gain: Serious Depth

The Suns were a surprise third team to step into the Dame deal. After trading for Bradley Beal and signing multiple veterans for depth, they just added Jusuf Nurkic and Grayson Allen to their roster. Nurkic is a lock to start now that Deandre Ayton is gone, and Allen was a starter for the Bucks last season, so his 3&D style of play should earn him the starting two or three spot over Josh Okogie.

A big part of why Phoenix lost to Denver in the second round of the playoffs last season was because they had no real depth. Now, contributors like Allen, Okogie, Yuta Watanabe, Bol Bol, and more will provide significant impact when the stars aren’t in.

Suns Lose: Deandre Ayton (In a Good Way)

It was clear that Deandre Ayton did NOT want to be a Phoenix Sun for a while. Last offseason, the center agreed to a deal with the Indiana Pacers, but the Suns quickly matched it to keep him in the desert. There were also reports of Ayton clashing with former head coach Monty Williams and teammates, but now those problems have been vanquished.

In his welcoming to Portland, Ayton seemed excited to have a fresh start. Averaging 18.0 points and 10.0 rebounds last season for a contender, there’s no way around it: the guy can hoop. We’ll see how he fairs with head coach Chauncey Billups, and as for the Suns, Jusuf Nurkic is a guy with no real problems attached, and he can still hoop nearly as efficiently as Ayton, averaging 13.3 points and 9.1 rebounds in 2022-23. Ultimately, it looks like things worked out for the better for both sides.

Boston Celtics

Celtics Gain: A True Point Guard

The Celtics may have just reestablished themselves as favorites to win the East. Boston lacked a true point guard, with Marcus Smart running that position for most of their possessions last season, and Malcolm Brogdon served as their sixth man, but he’s more of a scorer and has less impact in other aspects of his game.

Jrue Holiday proved he could be a difference maker on both sides of the floor, and he gets added to a trio with two other All-NBA talents in Jaylen Brown and Jayson Tatum. The scary part about all three of these players is they are known to be efficient scorers on offense, but lockdown perimeter defenders as well. For a team that was already second in defensive rating last season at 110.6, Boston only gets better from this trade.

Celtics Lose: A True Big Defender

While the C’s definitely got better replacing Brogdon with Holiday, they did lose Robert Williams III. While it seems minimal being that they already have Kristaps Porzingis and Al Horford manning the middle, the Time Lord’s impact is often overlooked. In the 2022 playoffs, Williams III averaged 6.2 rebounds and 2.2 blocks. In 2023, he averaged 6.0 rebounds and 1.3 blocks.

The bottom line is he is, at the very least, a good rim protector. While Porzingis and Horford can certainly hold their own defensively, keep an eye on Boston’s interior defense in comparison to their perimeter defense.

Share this article:

Jed Katz is currently a Journalism student at the University of Wisconsin-Madison. Originally from Bergen County, NJ, Katz was a writer and editor for the Northern Highlands Regional HS newspaper, as well as a sports anchor for the morning show. He's been invested in the game for years, both being a basketball junkie and playing as a 2-year varsity basketball player. Katz produces content surrounding the NBA, NCAA, and premier high school hoops.