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Eastern Storm: Damian Lillard and Jrue Holiday Swap Teams in Blockbuster NBA Trades

Damian Lillard’s inevitable trade request on July 1st, 2023 after his 11-year tenure with the Portland Trailblazers, caused great chaos as he and his agent tried to force a trade with the Miami Heat. After the slight tension between him, the organization and the fans, all parties pulled through and “Dame Time” did finally end up in Milwaukee Bucks, now expected to be one of the favorites to come out of the East. With the end of the Damian Lillard trade saga, the clouds cleared up on the trade market and Milwaukee’s biggest current rival in the conference Boston Celtics acquired Jrue Holiday.

In the three-team blockbuster trade with Portland and Phoenix, Milwaukee had to give up Jrue Holiday, a 2029 1st-round draft pick and two 1st-round pick swaps (2028,2030) to the Portland Trailblazers and Grayson Allen to the Phoenix Suns.

Following last year’s harrowing first round exit as the number one seed in the East and their two-time NBA MVP star Giannis Antetokounmpo’s callout to the organization “If I don’t feel that, I’m not signing” regarding his contract extension, Milwaukee felt the need to act and closed the deal. Let’s take a look at how this improves the team and how it deteriorates some key strengths the team had the previous years.

Milwaukee’s two most important drawbacks these past few years (other than Mike Budenholzer which I will not expand upon today) were always the primary ball handler problematic and the lack of a problem solver or rather an emergency valve on offense after Khris Middleton started to get regularly injured.

As great a player Giannis is, he is not prime Lebron James or Stephen Curry when it comes to being the main ball handler. Mostly used in the playoffs, teams always had a strategy against Giannis called “the Giannis Wall”, bringing a second player to help as soon as Giannis starts driving in, hoping to tear him down and tire him physically and mentally as the playoff series progresses. Even though most teams cannot outmatch the might of the Bucks, we saw better defenses and more physical teams succeed. Notably in the 2022 Eastern Conference finals, Giannis was disappointingly ineffective and seemingly tired with no fight left in him in Game 7 against the Boston Celtics. This became an effective strategy because Giannis doesn’t have an efficient shooting threat from behind the three-point line or from midrange, squeezing his offense to a relatively small area around the paint, opening himself up for a lot of physicality (like bumps and other collisions) which leads to great wear and tear on the body and the mind as he continuously suffers these for 39-44 minutes in the playoffs. Damian Lillard immediately solves this in great fashion, changing the geometry of the Bucks offense. How would he do that? By becoming the primary ball handler. According to sports analyst Eric Nehm, last season he “attempted 117 three-pointers from 30 or more feet away from the basket (…), the most of any NBA player [and] among players who attempted at least 50 three-pointers, Lillard recorded the longest average three-point attempt distance in the NBA at 27.67 feet.” Now as soon as Lillard passes half-court with the ball, he is a threat to the defense and they will have to put some kind of pressure on him extending the defense, opening up space for “the Greek Freak” Giannis to operate in the paint more as a finisher and less as a playmaker/ ball handler.

What about the problem-solving situation? Is Lillard up to that task? Well, when it comes to late game situations where everybody starts to tense up, lose rhythm and struggle, Damian Lillard thrives like no other superstar. Along with his series clinching buzzer-beaters in the playoffs against Houston and Oklahoma City, Damian Lillard has stunning clutch shooting statistics (clutch time is considered to be the final five minutes of the fourth quarter or overtime when the score is within five points). According to stats from, Lillard excels in “clutch squared” shots which make up just 1% of all shots taken but have the most significant impact on a team’s win probability. So, he is the man you want solving problems on offense when everything else stops working.

Following the Lillard trade one of the most interesting topics that came up was Jrue Holiday’s situation. As a team that recently drafted a prodigy in Scoot Henderson, the Trailblazers are a team looking to rebuild with a project that probably is going to take at least two to three years until they get over a 50/50 (W/L) season (41-41). Which means it is safe to say that they probably immediately started to discuss possible trade scenarios for Holiday, a veteran and not a future prospect, after acquiring him. Jrue Holiday also has a very compatible skill set that makes him desirable for possible contenders who want to further strengthen their hand. Reportedly, Miami Heat (after failing to capitalize a Damian Lillard trade), Los Angeles Clippers, Boston Celtics, Toronto Raptors and Philadelphia 76ers inquired about Jrue Holiday throughout the 4 days after the blockbuster Lillard trade until he finally got traded to the Boston Celtics for Malcolm Brogdon, Rob Williams, Golden State’s 2024 first-round draft pick and Boston’s 2029 first-round pick.

The question rises “Why did Boston make this trade?” First of all, Boston lost some toughness and perimeter-defense quality by trading Marcus Smart to the Grizzlies even though Smart’s defense was not really on point last season. They also lost a good and viable playmaker in Malcolm Brogdon (last year’s 6th Man of the Year) in this trade which the lack of one was Boston’s main problem for the last three seasons and it is really hard to say that Jrue Holiday is the guy to be the main playmaker of a team. Although Celtics didn’t really address their playmaker/decision maker-problem on the court with the Holiday trade, they added a better offensive option than Smart and found a player that could bring a similar tenacity on perimeter defense, hoping Jayson Tatum takes his final step on Superstardom and becomes a reliable and consistent primary ball handler/decision maker.

It seems all great but “did the Celtics lose anything from the trade?” Nothing other than their absolute best rim protector, considering Al Horford is now 37, and future prospects. The future draft picks are not really a great loss for Boston as the team wants to win now and not six or seven years later but losing Robert Williams III a.k.a. “Timelord” is definitely going to affect their paint defense as he is an exceptional defender down low. As mentioned by sports analyst Jay King “[even] while he dealt with injury issues last season, (…) they blasted opponents by 11.4 points per 100 possessions with him on the court.” Nevertheless, it is important to note that Rob Williams only played 35 games out of 82 last season, starting only 20 of those games, averaging 23.5 minutes on par with his constant knee and ankle injuries. Considering this fact, Celtics GM Brad Stevens decided to gamble to change things up in the team and paid a hefty price for the 33-year-old Holiday, creating arguably the best perimeter defense in the league with a Derrick White - Jrue Holiday backcourt while hoping Kristaps Porzingis or Al Horford can be a reliable threat to offenses that penetrate a lot to minimize this weakness throughout the season and the playoffs. Boston also cleared another roster spot with the trade and will probably try to sign bigs from the free agent market like Dewayne Dedmon and Bismack Biyombo during this season to have various options in the center position.

To end things off, it is safe to say that the Eastern Conference got a lot more interesting as the conference’s two favorites seem to be emerging stronger after the blockbuster Lillard trade from Milwaukee, which also helped Boston in the end. We will see how Boston’s head coach Mazzulla will try to regulate the defensive drawbacks and if Bucks’ new head coach Adrian Griffin can get the results the organization expects. We’re almost at the start of the regular season and have a ton to look forward to. On the 24th or the 25th of October (depending on where you are in the world) we all will wake up to a new dawn, a new season, a new trip in the land of basketball. So, let’s see what this 2023/24 NBA season has to offer.

Written by: Yiğit Gülmez

Edited by: Bilge Öztürk

Works Cited:

  • Cover photo by Juan Ocampo. Copyright 2023 NBAE (Photo by Juan Ocampo/NBAE via Getty Images)

  • Kaan Kural & İnan Özdemir. Lillard Takası ve NBA 2023-24 Atlantik Grubu Rehberi. Socrates Dergi Youtube Channel. October 2023.

  • Kaan Kural & İnan Özdemir. NBA 2023-24 Merkez Grubu Rehberi. Socrates Dergi Youtube Channel. October 2023.

  • Kaan Kural & Orkun Çolakoğlu. Atlantik & Merkez Grupları. Socrates Club Youtube Channel. October 2023.

  • Kaan Kural & Orkun Çolakoğlu. Jrue Holiday Celtics’te Güneydoğu & Kuzeybatı Grupları. Socrates Club Youtube Channel. October 2023.

  • Panerio, Jonas. "If I don't feel that, I'm not signing" - Giannis Antetokounmpo remains non-committal regarding contract extension with the Milwaukee Bucks. Bucks Zone Fan Nation. August 2023.

  • NBA Insiders. Damian Lillard traded to Bucks: Big questions after the most shocking deal of the NBA offseason. ESPN. September 2023.

  • Beuoy, Michael. NBA Clutch Shooting Report for Damian Lillard.

  • Charania, Shams and Sam Amick. How the unexpected blockbuster Damian Lillard trade to the Bucks came together. The Athletic. September 2023.

  • Nehm, Eric. How Damian Lillard transforms the Bucks’ offense — both in geometry and gravity. The Athletic. September 2023.

  • Kenyon, David. Ranking the Most Clutch NBA Players Since 2000. Bleacher Report. November 2021.

  • Martin, Brian. Stats breakdown: Finalists for Kia Clutch Player of the Year. April 2023.

  • Basketball Reference. Robert Williams.

  • Helin, Kurt. Five possible landing spots for Jrue Holiday. September 2023

  • King, Jay. Is Jrue Holiday the missing piece the Celtics have been waiting to obtain?. The Athletic. October 2023.

  • Fox Sports. Robert Williams III Injuries.

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