So, Damian Lillard is now a Milwaukee Bucks. That means he is going to play alongside Giannis Antetokounmpo. That means they are going to be very good in the Eastern Conference. And that does not bode well for the Boston Celtics. In fact, the Bucks have already jumped the Celtics as the favorites to lift the Larry O'Brien trophy next June following their acquisition of Lillard. So what's the move, Boston? Perhaps they can trade for the main piece Milwaukee gave up to the Portland Trail Blazers to land Dame Time: Jrue Holiday.
Milwaukee and Boston have now positioned themselves as the top two teams in the East. Though based on Richard Jefferson's comments regarding both squads' offeseason moves, it seems like the Bucks have the edge and have gotten much better with the changes they made this summer. With that said, the ball is now in Boston's court. In fact, Brad Stevens is apparently already back on the drawing board looking to cook up another Celtics trade that could potentially bring Holiday to Beantown.
Let's take a look at the perfect trade the Boston Celtics can offer the Portland Trail Blazers for Jrue Holiday following the Damian Lillard blockbuster deal.
Celtics trade for Jrue Holiday
The Celtics have one disgruntled player on their roster in Malcolm Brogdon, so they might as well try to see what they can get for him. In this deal, Boston taps on the Indiana Pacers to orchestrate a three-team trade with the Blazers.
Boston Celtics receive: Jrue Holiday
Portland Trail Blazers receive: Buddy Hield, Robert Williams, Celtics 2024 1st round pick (via Warriors), Celtics 2025 1st round pick, two Celtics 2024 2nd round picks
Indiana Pacers receive: Malcolm Brogdon
Why the Celtics do this deal
In this trade, Boston gives up a couple of their key players from their rotation in Malcolm Brogdon and Robert Williams. While their losses would hurt, there is a case for the Celtics to trade them if it means landing Jrue Holiday.
As mentioned, Brogdon isn't too pleased with the Celtics organization right now. In case you missed, Boston already attempted to trade the reigning Sixth Man of the Year to the Los Angeles Clippers earlier this offseason in the initial Kristaps Porzingis deal. However, the Clippers backed out of the trade due to concerns about Brogdon's health.
As for Williams, Boston acquiring Porzingis means they see the 25-year-old center as expendable. As terrific a defensive presence Time Lord has been for Boston over the last couple of years, his inability to stay healthy has hurt Boston. Williams played just 36 games last season and has only played one 60-game season in his five-year career. While he helps defensively, his lack of availability doesn't really make him much of a huge loss.
Meanwhile, Holiday gives the Celtics the Marcus Smart replacement they've been looking for and a lot more. Obviously, the 5-time All-Defensive member will bring the same kind of defensive tenacity and energy that Smart provided the Celtics for nine seasons.
Moreover, Holiday is a much better offensive player than Smart will ever be. He is capable of facilitating and can call his own number when needed. The Celtics have long needed another ball handler to play alongside Jayson Tatum and Jaylen Brown and play the role as lead facilitator.
With that, Holiday checks both boxes as someone who can playmake and defend for the Celtics.
Why the Blazers do this deal
As for the Blazers, they do this deal by acquiring a couple of high-level role players in Buddy Hield and Robert Williams. Hield is one of the best shooters in the NBA and Williams is a terrific interior defender. They likely won't be Blazers for long since they don't necessarily match Portland's young timeline. Nonetheless, Hield and Williams' team-friendly deals should make it easy for the Blazers to flip them for more assets. Hield's $18.5 million contract this season expires next summer, while Williams still has three years, $37.3 million remaining on his current deal.
In addition, the Blazers also get to load up on their draft capital with two first round picks and a couple of second rounders. All in all, the assets they get in trading away Damian Lillard include Hield, Williams, Deandre Ayton, Toumani Camara, three first round picks, a pick swap, and two second round picks. That's a pretty good haul for an aging 33-year-old star. And it may not stop there if the Blazers are able to flip Williams and Hield elsewhere.
Why the Pacers do this deal
As for Indiana, they agree on this deal to trade away a player who no longer wants to be there in Buddy Hield. Hield and the Pacers failed to agree on a contract extension. The Pacers did offer the sharpshooter a deal, but the contract reportedly did not make Hield “feel desired” — whatever that means. Nonetheless, the Pacers may be better off flipping the seven-year guard and getting Malcolm Brogdon back.
Brogdon spent three seasons with the Pacers from 2019 to 2022 and had some of his best individual seasons with the franchise. Now on the way to turning 31 years old, Brogdon brings a veteran presence to a young Pacers squad that is looking to get to the next level. He could be a valuable veteran mentor for Tyrese Haliburton, who made the All-Star team last year and should be a prime breakout candidate over the next couple of seasons.