The transaction that sent Jrue Holiday to the Celtics produced both winners and losers

Is it possible that the Eastern Conference currently contains the top two teams in the NBA?

It’s possible that Denver and Nikola Jokic will have something to say about that, but the arms race in the Eastern Conference has allowed a couple of clubs to put some distance between themselves and the rest of the pack in that conference. The Milwaukee Bucks began their offseason by acquiring Damian Lillard as their first player.

In response, the Boston Celtics made a trade on Sunday to acquire former Buck Jrue Holiday. This sets up a potential clash between Lillard and Holiday in the playoffs for the Eastern Conference. Let’s examine who came out on top and who came out on the losing end of this deal.

To begin, the following is a rundown of how the exchange works:
This is what Boston gets: Junior Holiday
In exchange, Portland receives: Robert Williams, Malcolm Brogdon, a first-round pick from Golden State in 2024, and a first-round pick from Milwaukee Bucks in 2029.

The Boston Celtics came up on top.

The city of Boston needed to take some aggressive action. It wasn’t just that Milwaukee made its own power move in trading for Lillard; it was also that the Bucks made one that went right at the heart of the Celtics. Boston parted ways with former Defensive Player of the Year Marcus Smart in order to acquire Kristaps Porzingis, bringing in a large player who Lillard has a history of abusing in the pick-and-roll game. The result was an unfavorable matchup for Boston in the playoffs.

Holiday is an upgrade offensively, particularly in terms of how the attack is organized, and is not that far off from being on par with Smart in terms of the caliber of defender he is (Smart should do well in Memphis). The showdown with Milwaukee will be different after the holiday.

Following the completion of this transaction, the Celtics will likely have the greatest six-man rotation in the NBA. This rotation will consist of Derrick White, Holiday, Jaylen Brown, Jayson Tatum, and Kristaps Porzingis. You may identify holes in their depth after that group, and there are reasons to be concerned about Kristaps Porzingis’s health given that he is returning to practice after having a foot ailment; however, you will find the same kinds of small worries with any contender. Genuinely contending for the championship is Boston’s status at this point.

The winnings will go into Jrue Holiday’s bank account.
Is it a good thing for Jrue Holiday that he no longer has to play alongside Giannis Antetokounmpo but instead now has to play alongside Jayson Tatum? That can be argued either way.

The fact that the Bucks were already deep in the luxury tax and Holiday is up for a contract extension, a discussion that was bound to turn sticky, is not debatable. The Bucks were already deep in the luxury tax. Now, he’s with a Boston squad that reportedly wants to keep him around for longer, and he’s interested in cooperating with them. It’s possible that this combination will maintain the Celtics in the top tier of the Eastern Conference for at least a few more years, while also securing Holiday the next contract that he desires.

The Philadelphia 76ers were the losing team.
There was a time, just a few months ago, when Boston, Milwaukee, and Philadelphia were the only three teams who could be considered serious contenders coming out of the Eastern Conference for the upcoming season. Both Milwaukee and Boston have made substantial improvements to their rosters since that time.

Not only did Philadelphia fail to make any upgrades, but the team also enters training camp with James Harden unhappy and requesting a trade. In light of all of that, Joel Embiid’s post on X (which was once known as Twitter) comes off as being a little bit sarcastic.

Embiid is still the primary focus of the 76ers and general manager Daryl Morey’s attention; the player has expressed a desire to win a championship with either the 76ers or another team. Reportedly, he also informed the organization that he would stay with them through whatever happened with Harden, but other teams are keeping a watch on Embiid in the belief that he could be the next superstar to leave his current team. Any major decision like that will most likely not be made until the summer of next year. On the other hand, nobody can predict how he will behave if, at the end of this season, he surveys the Eastern Conference and sees a significant disparity between his club and the Celtics and the Bucks.

The Portland Trail Blazers came up on top.
I loved the first part of the Damian Lillard trade, but the final determination could not be made until we saw what the club got back from flipping Justin Holiday. When I named the winners and losers from the Damian Lillard trade, I stated Portland was TBD. I liked the first part of the trade, but the final determination could not be made until we saw what the team got back from flipping Holiday.

At this point, it is safe to say that Portland is the victor. The following players and draft picks were acquired as part of the Damian Lillard trade: DeAndre Ayton, Robert Williams III, Malcolm Brogdon, a first-round selection from the Warriors in 2024, an unprotected first-round pick from the Celtics in 2029, an unprotected first-round pick from the Bucks in 2029, and two pick swaps with the Bucks in 2028 and 2030. I’m sorry, Miami, but they did much better than they could have anywhere else with that haul.

Do not be surprised if either Brogdon or Williams are dealt by the time the deadline in February rolls around and the Trail Blazers add more players to their pile. It’s also possible that the Blazers have decided that Williams is a better fit for their team after observing Ayton and Williams playing together in their rotation.

Robert Williams and Malcolm Brogdon are currently considered to be the game’s losers.
This is not intended as a criticism of Portland, but for veterans to go from a team that was a title contender (which Boston was even before this deal) to a team that is rebuilding is a step down. Both could be made available for trade before the deadline, but early rumors indicate that Williams, in particular, could be remaining with the team for some time to form a frontline combination with Ayton.

Loser: the Heat, the Clippers, and other teams that were holiday suitors
There was a large list of teams that entered the Holiday sweepstakes, but the elimination of a number of those teams is very painful.

Since a few years ago, the Los Angeles Clippers have been in need of an upgrade at the point guard position; nevertheless, they have not been able to pull off a significant trade. Holiday would have been a much greater addition to the Los Angeles Lakers’ squad than the long-rumored trade for James Harden, which, according to the most recent reports, is no longer a possibility. Now, the Clippers will not have the opportunity to acquire Lillard or Holiday. They are still a club that poses a threat, but it is a significant “if” that Kawhi Leonard and Paul George will be healthy for the playoffs. Even if they are, the question is whether or not they will be able to upset Denver or Phoenix without making any roster additions.

Things should go well in Miami. We will see contributions from players we did not anticipate, as they always do for the Heat, and Tyler Herro will be coming back. Despite this, it does not appear that this squad has the ability to compete in the Finals again. Not without the contributions that Gabe Vincent (now with the Laker) and Max Strus (with the Cavaliers) made on the court. In spite of the fact that Miami possesses a squad that, with the addition of a top-tier point guard, might pose a threat to once again emerge victorious from the Eastern Conference, the Heat’s trade assets and connection with the front office of the Trail Blazers led to two missed opportunities for the Heat. It will be difficult for them to climb back to the top of the conference now.

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