The Boston Celtics continued an offseason remodeling Sunday by agreeing to acquire All-Star guard Jrue Holiday from Portland.
With the Trail Blazers looking to move Holiday after netting him in the Damian Lillard blockbuster last week, the Boston front office struck quickly. In a trade that will reshape the Celtics’ vision for the coming season, the team agreed to send Malcolm Brogdon, Robert Williams III, Golden State’s 2024 first-round draft pick and an unprotected 2029 first-round pick to Portland.
OFFICIAL: Trail Blazers Acquire Robert Williams III and Malcolm Brogdon
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— Portland Trail Blazers (@trailblazers) October 1, 2023
The Celtics weren’t alone in pursuing Holiday after it became clear the Blazers planned to find a new home for him. The 33-year-old drew interest from a long list of playoff teams, including the Clippers and 76ers. The robust market for Holiday likely contributed to the hefty price tag Boston needed to pay. Two league sources, who were granted anonymity in order to speak freely, said the Celtics would not have been able to push the trade to the finish line without offering Williams. To land Holiday, Boston also needed to part ways with Brogdon, the reigning Sixth Man of the Year award winner, and significant draft capital. The amount of value the Celtics traded raised some eyebrows around the league, but so did the idea of Holiday joining Jayson Tatum and Jaylen Brown in Boston.
The Celtics paid up to land a two-way impact player who they hope can help deliver a championship. Holiday, 33, averaged 19.3 points, 7.4 assists and 5.1 rebounds per game for Milwaukee last season while making the All-Star Game for the second time in his career. Widely regarded as one of the league’s best defensive guards, he also was voted onto the First Team All-Defense for the third time.
He should replace the versatility and tenacity Boston lost by trading Marcus Smart earlier in the offseason. Heck, Holiday’s one of the only guards in the NBA who could be an upgrade from Smart at his best on that end of the court. With Derrick White, the Celtics will have two All-Defensive team members in the backcourt next to their two All-NBA wings. Add in Kristaps Porziņģis and Al Horford, who will lead the interior resistance, and Boston has the makings of another elite defense after finishing second on that end of the court last season.
The Celtics will still miss Williams’ ability to shut down the paint. As productive and efficient as Brogdon was last season, the loss of the 25-year-old shot blocker could hit Boston harder. When healthy, Williams is one of the few big men who pairs elite shot-blocking talent with feet quick enough to stay in front of guards on the perimeter. Even while he dealt with injury issues last season, his ability to transform the Celtics shined through; they blasted opponents by 11.4 points per 100 possessions with him on the court. It was the second straight season they had a double-digit net rating with Williams in the lineup.
With him, Porziņģis and Horford in the frontcourt, the Celtics spent the summer planning to use a steady diet of double-big lineups loaded with rim protection. The addition of Holiday will likely lead to more regular use of smaller lineups, though Joe Mazzulla will still have the option of pairing Porziņģis next to Horford or even backup center Luke Kornet. Williams’ departure should leave Kornet with a bigger role than anticipated.
The trade also freed up another roster spot, which the Celtics could use to replenish some of the frontcourt depth. They have reached an agreement to bring big man Wenyen Gabriel to training camp, as The Athletic’s Shams Charania reported. Other established centers still available include Bismack Biyombo, Dewayne Dedmon and Gorgui Deng. Blake Griffin, who the Celtics deeply appreciated last season for his help both on and off the court, also remains unsigned.
Gabriel’s strong play for South Sudan in the FIBA World Cup this summer helped secure the team’s first-ever spot in the 2024 Olympics. Gabriel averaged 9.2 points and 6.8 rebounds for South Sudan, and has worked out for the Celtics in Boston in recent weeks.
— Shams Charania (@ShamsCharania) October 1, 2023
While Williams had the higher trade value of the two players Boston sent to Portland, Brogdon certainly wasn’t just a throwaway. He finished fourth in the NBA in 3-point percentage while averaging 14.9 points per game off the Celtics bench. Before dealing with an elbow issue late in the playoffs, Brogdon scored at least 12 points in 13 of Boston’s first 15 playoff games. He provided steady, instant offense for the Celtics second unit, but the relationship between him and the organization grew complicated this summer after the team nearly traded him to the Clippers, as The Athletic’s Jared Weiss wrote in a story about Brogdon’s departure. That’s no longer an issue for Boston.
The Celtics won’t be as deep after this trade, but their top six players (in some order: White, Holiday, Tatum, Brown, Porziņģis, Horford) could represent the league’s best core. Beyond that nucleus, Joe Mazzulla will need to hash out the back end of a rotation that will likely include Payton Pritchard, Sam Hauser, Oshae Brissett and/or Kornet with several other players vying for minutes behind them.
Boston’s starting lineup is still to be determined. Mazzulla could go smaller with White and Holiday in the backcourt or larger with Horford next to Porziņģis in the frontcourt. Either way, the Celtics should have nothing but two-way players in their first unit with the option to toggle back and forth between bigger and smaller lineups. Mazzulla will need to tweak some of his ideas for the coming season to fit Holiday into the plans and to account for Williams’ absence, but Boston believes Holiday could be the missing piece. The Celtics moved two gifted and productive players to acquire him, but both have health concerns moving forward. Though Holiday’s age comes with concerns of its own, he has typically been pretty durable throughout his career.
Beyond the possibility that Williams reaches his considerable potential elsewhere, is there a possible downside to this deal for Boston? The Celtics were lined up to build an identity around size and outside shooting, but lost some of each trait in this trade. They now have less frontcourt insurance in case the 37-year-old Horford begins to experience a significant decline or Porziņģis deals with injury problems again. Holiday has been a solid 3-point shooter during the regular season (he shot at least 38 percent from deep during each of his three seasons in Milwaukee) but hasn’t sustained that type of accuracy during the playoffs. His postseason shooting percentages are actually kind of bleak; he hasn’t shot better than 32 percent from behind the arc during a single postseason since he was with the 76ers more than a decade ago.
Over three playoff runs with the Bucks, he shot a combined 39.6 percent from the field. His career true shooting in the playoffs is 50.2 percent, less than Smart’s playoff true shooting of 53.2 percent. That could become a problem if Holiday is again forced into inefficient scoring during the games that matter most.
On a similar topic, a Celtics-Bucks series would now be epic. It’s quite a development that Milwaukee’s decision to offer Holiday for Lillard also ended up indirectly helping the Celtics, the Bucks’ chief competition in the East.
Even with stretches of ugly playoff shooting, Holiday helped the Bucks win a championship. He is regarded as one of the NBA’s best teammates and locker room forces. And he will give the Celtics another one of the league’s premier perimeter stoppers, making their defense one of the league’s most switchable yet again. Though he only has one year left on his current contract at $36.8 million plus a player option for $37.4 million the following season, Holiday will become eligible to sign an extension in February. The Celtics naturally made this deal with the hope of keeping him long-term. They see Holiday as a great complement to their best players both on and off the court. He was believed to consider Boston one of his preferred destinations after the Bucks traded him last week.
After falling short deep in the playoffs several times during recent seasons, the Celtics decided not to just try again with a similar group. They shipped away four rotation pieces in Smart, Brogdon, Grant Williams and Robert Williams. They acquired two former All-Stars in Porziņģis and Holiday. The Celtics will at least be different. They could also be better. And maybe, just maybe for Celtics fans, they will finally be good enough.
(Photo: Stacy Revere / Getty Images)