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Boston Celtics Execute A Trade Of Trade-Offs

Jrue Holiday Boston Celtics
(AP Photo/Lynne Sladky)

A win-now mode move doesn’t do enough justice in describing the move made by Brad Stevens and the Boston Celtics on Sunday. The Celtics agreed to acquire recently moved All-Star guard Jrue Holiday from the Portland Trail Blazers for Malcolm Brogdon, Robert Williams, and two unprotected first-round picks in 2024 (from the Golden State Warriors) and 2029. 

The Celtics’ desire to stay close to the Milwaukee Bucks and eliminate another Eastern Conference contender by adding Holiday made the trade possible. There is more to this trade, too. As the great philosopher Shrek would say, this trade has layers like an onion. Boston used the transaction as a trade-off between winning now and preparing for the future. It is also a trade-off between team continuity and talent optimization. 

The trade-off results in a must-win scenario for the Celtics. That’s because of the prior moves made this offseason by the Celtics to swap Marcus Smart for Kristaps Porzingis and not retain Grant Williams. The emphasis is clearly in the right now. Here’s what’s at stake and why the trade means more than just running next to the Bucks. 


Solving The Brogdon Situation

One of the lingering needs for the Celtics heading into the season was the lack of depth at the guard position. After trading Smart, Boston was left with Derrick White and Payton Pritchard in the backcourt, along with JD Davidson and new addition like Dalano Banton, who are long shots to earn significant minutes. Brogdon, of course, would have had a spot in the rotation. Still, the fallout from his own involvement in the original iteration of the Porzingis trade soured the relationship with the Celtics. Additionally, Brogdon’s health status was murky at best. The interest in adding the multiple-time All-Star became high when Holiday hit the market. 

Brogdon’s play last year was a reason the Celtics were the second seed in the East. Much of the reasons he shined in Boston will allow White to play the role that Brogdon played last season. Adding Holiday also improves the Celtics’ back-court defense after losing Smart. With Brogdon’s defense exposed as shakey in some of their later playoff games, Holiday and White are a well-rounded defensive tandem equipped to match up against any team.


A Shrinking Window

Behind Jaylen Brown and Jayson Tatum, Robert Williams was the roster’s third-longest consecutively tenured Celtic. Above that, he was Brown and Tatum’s close friend and teammate. His presence will be missed on and off the court, especially this close to the beginning of the season. Williams was also set up to be on the team until 2026. 

Boston had come close with Williams at winning a title, most notably in 2021 but also last season. So why did they move on from a 25-year-old big man who was on a team-friendly contract? In their calculus, Boston looked at those two seasons and concluded that Williams only played in 96 of a possible 164 games. Similarly, Williams was hobbled during the playoffs, which limited his effectiveness when they needed him most. Granted, in recent seasons, some of the best versions of the Celtics teams have seen Rob Williams featured. 

The Celtics hope to overcome that by maximizing the talent on their roster. If we acknowledge that Derrick White was already the best guard last season for Boston, then the evaluation of Holiday over Smart and Porzingis over Williams is much more palatable. It also can’t be ignored that the Celtics front office felt pressure to snag Holiday after the next biggest horse in the east, the Milwaukee Bucks, acquired Damian Lillard. By loading up, they believe that a showdown with the Bucks is inevitable. Lastly, the Celtics are going on year seven of the Jayson Tatum and Jaylen Brown partnership. The time to win gets shorter by the day, and they don’t want to leave empty-handed again. 


New Players, Similar Set-Up

The biggest shift in the trade is three months old. The Celtics were in the midst of a vastly different roster breakdown than in years past. They had reconstituted themselves from a guard-heavy team to a front-court-heavy team. That made sense due to multiple different attempts at guard pairings over the years and the durability risks surrounding Williams and Horford. With the addition of Holiday and the exodus of Williams, the roster is similar to last season’s. 

A lot of attention now turns to the availability of Horford and Porzingis this season. Coming off his most games played since 2016-2017, there is hope he can make it to around the same mark. However, Porzingis was rehabbing a bout of plantar fasciitis in the offseason. Horford, on the other hand, has been resilient as a center for the Celtics. His decline was noticeable in the later rounds of the playoffs. Much of that was the Celtics’ fault for not finishing the series early. Horford has been committed to his body and conditioning. 

Jrue Holiday brings the Celtics another elite on-ball defender, mirroring what they had with Smart at the top of their defense. On Offense, his contributions will be more than what Smart brought, but his role could be similar in initiating the offense. Holiday differs in his demeanor, but his pedigree and success in the league could help a Celtics team that has lacked maturity and calmness in times of pressure. 

This trade will surely be the talk of Celtics media day, which takes place on Monday, October 2. It’ll be interesting to hear from Brad Stevens and Joe Mazzulla and what they have to say. But perhaps more insightful might be the words from Tatum and Brown. As the two stars who the front office has shaped the team around, they must be feeling a bevy of emotions, including the pressure to get it done this year. 


Matt Strout is a contributor to Back Sports Page. Matt studied Journalism and Sociology at Temple University for four years and graduated in May of 2022. While there, Matt wrote for multiple student and professional publications covering sports and the City of Philadelphia. Matt is originally from Maine and now resides in California. He has written content primarily for the NBA and PGA Tour. You can catch Matt frequently as a guest on the “Cut The Nets” podcast featured on the Back Sports Page network. When Matt is not writing, he enjoys cooking and playing golf. Follow Matt’s social media on Twitter @TheRealStrout or Instagram @matt_strout96 

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