By Avi Tyagi


The Milwaukee Bucks’ deal for Dame was risky, unprecedented, and timed to perfection. Here’s how.

Jrue Holiday had been a core member of the Bucks for the past 3 seasons. According to my per-game estimates, he was an All-Star caliber player for the past 2 seasons, as well as for several seasons in NOLA. Jrue’s been the best true two-way guard in the league. For the last 7 seasons, Jrue has averaged 3.5+ deflections per 48 minutes (per, always ranking in at least the top-10 amongst all guards to play 1800+ minutes. All the while, he’s often taken the toughest assignments in both the regular season and playoffs. His defensive performance against Damian Lillard in the 2018 first round felt like a pivotal turning point in Dame’s own career arc. His work on taller foes such as Booker, DeRozan, and LaVine has been crucial to winning playoff series. Having already lost Jevon Carter to Chicago, Milwaukee opens the season with some of the weakest perimeter defense across the whole league. It’s the fly in the ointment that could crater hopes and dreams in the later rounds of the playoffs. 

At the same time, Holiday’s been a beacon of regular season efficiency to partner with Giannis for the last 3 seasons. While not much of a pull-up creator or shotmaker from distance, Jrue drastically improved his 3 point percentage over the course of his Pelicans career and arrived to Milwaukee as an excellent catch and shoot option capable of mixing in pull-ups. Over the last 3 seasons, Jrue shot 45.9% on 16+ feet middys and 39.5% from 3 over the last 3 seasons, despite only being assisted on 46% of his triples (side note: Jrue’s a great fit in Boston. They needed a primary passer, an excellent, disciplined perimeter defender, and a medium-usage scorer with a promising history of knocking down spot up 3s. Jrue provides that all in one package). In a big 3 with Khris and Giannis, Jrue gained the opportunity to be more selective as a ball handler than at any prior point in his career. As such, Jrue attempted fewer shots on congested drives and improved his shooting profile. Jrue finished the 2019-20 season as an overtaxed ball-handler with a 53.7% true shooting mark. His next 3 seasons with the Bucks: 59.2%, 59.3%, 58.6% (the three best marks of his career). With the Bucks, Holiay’s rim field goal rate dipped to career lows (only 22.9% of his shots over 3 years) but he finished at the rim at a career-best rate over that stretch (69.4%). There is no guard like him in the league. He’s a tremendous leader and individual. 

Aside from just the basketball, the financial components of this transaction are heavy. Lillard will be making approximately 35% of the cap in his age-35 and age-36 seasons. In the super-apron era, those costs cannot simply be waived away. There is a distinct possibility that for one reason or another, a team with 6 core players, all 28 or older, age out in a synchronized decline and don’t win a ring in their next 2 seasons. In 2025-26, Lopez, Connaughton, Portis, Middleton, and Giannis could all split from the team, leaving Milwaukee in a rebuild with few assets and only Lillard’s contract on the books. He’s Damian Lillard so it’s entirely conceivable that they win and he plays up to All-NBA quality in his mid-30s. It’s just worth mentioning. In fact, over the last 15 years, no established multi-time All Star has ever been traded for an ALL-NBA player under team contract for 3+ seasons. Such is the distinctive nature of this deal. 

That being said, we know why this trade occurred. I love Jrue, but the last 3 playoffs have implicitly showcased a lack of offensive cohesion with Giannis in the playoff settings. For as much as Jrue has steadily evolved his game to become a more potent 3-point shooter, he’s still an inside-out player. Asking him to rely on a heavy dose of self-created pullups in a playoff atmosphere with a congested paint led to truly putrid results. In each of the last 3 seasons, Jrue’s taken 2 more pull-ups per game including 1 more pull-up 3 per game in the playoffs versus the regular season. That increased usage has not led to increased productivity. Jrue’s shooting percentages have plummeted and his true shooting percentage has dipped down to 47.6% over the course of 40 playoff games with the Bucks. For context, that would be in the bottom 4% league wide if those were regular season percentages. Enter Dame.

Damian Lillard is a true spaced-out innovator. His deep 3s are the stuff of legend and he has prospered for years now by operating in the high pick and roll or rejecting screens entirely and simply canning deep 30 footers. He’s a dominant 3-level scorer and will be a sight for sore eyes in the clutch after the questionable decision making of Bucks’ playoffs past. Gone will be the days of miserable entry passes to Giannis. Arriving in is one of 6 players last season (with a 35 game minimum) to average a true shooting percentage above 65% on a usage rate over 24%: Lillard, Jokic, Butler, Embiid, Steph Curry, and Kevin Durant. He’s phenomenal, folks! Additionally, this was the only year the Bucks could truly make a swing for this sort of player. After an offseason noted mostly for Giannis’ comments to set the stage for potentially leaving, the Bucks have provided him the sort of A+ Go-To shot creating partner he’s never had before. Starting from next season, teams over the super apron can no longer include cash in trades, no longer use prior trade exceptions or aggregated trade exceptions, and will start having picks frozen and moved around as part of the draconian punishments. This was the year to do it. Welcome to Fiserv Forum, Lillard. Dame Time begins now.