NBA franchises constantly shuffle their deck, hoping to stack the championship odds in their favor. This offseason, multiple teams made moves that altered not only their immediate aspirations but their futures as well. 

While casual NBA fans may only consider how deals would impact the upcoming season, Sports Business Classroom teaches a broader point of view, focusing on how transferring players and assets might impact both teams given their organizational goals. 

In this series, we will take a trip down memory lane and see how the 2023-24 offseason deals have progressed and how they could impact each team’s roster construction moving forward, starting with the “Lillard” and “Jrue” trades.

Damian Lillard Trade

To Milwaukee Bucks: Damian Lillard (via Portland Trail Blazers)

To Trail Blazers: Deandre Ayton (via Phoenix Suns), Toumani Camara (via Suns), Jrue Holiday (via Bucks), a 2029 first-round pick (via Bucks), two first-round pick swaps with Bucks (2028, 2030)

To Suns: Grayson Allen (via Bucks), Keon Johnson (via Blazers), Nassir Little (via Blazers), Jusuf Nurkic (via Blazers)

Initial Grades

Bucks: B+

Trading for Lillard opened a four-year championship window for the Bucks. Neither star has ever played with a teammate of this caliber. The pairing can also create one of the most formidable pick-and-roll duos in the NBA. They may have growing pains, but the Bucks are title contenders as long as the two are healthy. However, the Bucks lack assets for future moves if things do not pan out.

Trail Blazers: A

General Manager Joe Cronin and the rest of the Portland front office came away from the Lillard trade in a good spot. The team added former first-round pick (2018) Deandre Ayton to a young core with Anfernee Simons, Shaedon Sharpe, and Scoot Henderson. Is Ayton part of the long-term future? The change of scenery from Phoenix may help Ayton reach greater heights.

Suns: B-

Phoenix added multiple role players for Ayton, including Allen, Little and Nurkic (who will be the de facto roll man). The move helped replenish some of the depth given up to acquire Bradley Beal. Injuries may be a concern, and the Suns only have a little left to move if the team underperforms.

Quarter Grades

Bucks: B-

As of December 12th, Lillard leads the league in clutch points, per NBA.com and Antetokounmpo is still performing at an elite level. Still, the Bucks have many kinks to work out.  Can the Bucks better utilize what could be an elite pick-and-roll combo between the two stars? Will Khris Middleton get healthy enough to play without a minute restriction?

Trail Blazers: A+

The Blazers are bad right now, but the players and assets accumulated via the trade are worth it for the long term. Toumani Camara is currently first in net points per 100 possessions among rookies, per Cleaning the Glass.

Suns: Incomplete 

Making conclusive judgments on the Suns’ offseason moves while Beal is injured is difficult. Allen and Nurkic have logged the second and fourth-most minutes, respectively, while Nassir Little has found himself in a more minor reserve role. Heavy minutes from Allen and Nurkic point to them being among the role players that might make or break this season once (if) Beal is healthy. 

Jrue Holiday Trade

To Boston Celtics: Jrue Holiday

To Trail Blazers: Malcolm Brogdon, Robert Williams III, 2024 1st-round pick (via Golden State Warriors), 2029 unprotected 1st-round pick (via Celtics)

Initial Grade:

Celtics: A+

Boston brought an elite defensive point guard in Holiday to replace what was lost with Marcus Smart (earlier to the Memphis Grizzlies for Kristaps Porziņģis). Adding Holiday to a backcourt with Derrick White is a fantastic backcourt. The Celtics lose some depth but might have the best top six players in the entire NBA. 

Trail Blazers: A

Trading Holiday, a win-now player on a rebuilding team in Portland, for additional picks and players with trade-friendly contracts not only bolstered the Blazers’ future but also instilled hope in the franchise.

Quarter Grade:

Celtics: A+.

As of December 12, the Celtics have the best net rating by more than two points, per Dunks and Threes. Holiday, White, and Jaylen Brown are all reliable defenders on the perimeter. Jayson Tatum is continuing his ascension as one of the best players in the NBA.

Trail Blazers: A

Williams’ season-ending surgery is tough for both the player and the team. Brogdon is performing at a high level and might be traded to a title contender before the trade deadline.