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How the Celtics landed Jrue Holiday and created a lineup that will be hard to beat

The Celtics added Jrue Holiday to their backcourt at a high cost, dealing Malcolm Brogdon, Robert Williams, and two first-round picks to Portland.Aaron Gash/Associated Press

After the Bucks became NBA title favorites with Wednesday’s seismic deal for superstar guard Damian Lillard, they may have unintentionally created opportunity elsewhere, and the Celtics were prepared.

Milwaukee sent another All-Star guard, Jrue Holiday, to the Trail Blazers in the deal, and Portland had no intention of keeping a 33-year-old who did not fit its youth movement. Numerous teams contacted the Blazers about Holiday, but a league source said the Blazers then engaged a smaller group of teams that had assets it coveted.

Initially, the source said, Portland was seeking a haul that included four or five future first-round picks. But that demand softened, and on Sunday the Celtics struck, agreeing to send Malcolm Brogdon, Robert Williams, the Warriors’ 2024 first-round pick that was previously acquired, and the Celtics’ 2029 first-round pick in exchange for Holiday.

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Celtics ownership has given a clear directive to the front office to do whatever it takes to win the franchise’s first title since 2008, and this move is a loud step in that direction. Boston can unfurl a starting five of Jayson Tatum, Jaylen Brown, Al Horford, Kristaps Porzingis, and Holiday that should be considered the league’s best.

Holiday, 33, averaged 19.3 points, 7.4 assists, and 5.1 rebounds per game last season. The first-team All-Defensive selection instantly fortifies a unit that appeared wobbly following the departure of 2022 Defensive Player of the Year Marcus Smart. Holiday is also a well-respected leader and will be an important voice in Boston’s locker room.

He will make $36.9 million this season and has a $39.4 million player option for next year, but league sources said both sides view Holiday’s arrival as the start of a long-term partnership.

The Blazers were not required to make a deal that suited Holiday, but a league source said the guard’s camp provided Portland with a short list of preferred destinations, and the Celtics were on it.

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The admiration was clearly mutual. A league source said that when Holiday played for the Pelicans in 2020, the Celtics spoke at length with New Orleans about a potential trade before the Bucks eventually made the better offer. Holiday then helped the Bucks win an NBA championship in his first year with the team.

The Celtics are hopeful that history will repeat itself.

Although Portland was mostly seeking draft capital, the Celtics needed to send back nearly $34 million in salary for matching purposes, so it was clear that any trade would result in a substantial hit to the regular roster, too.

A league source said the Blazers made it clear that Williams, the oft-injured but athletic big man who has shown flashes of dominance, needed to be part of the deal. Williams appeared in just 35 games last year, averaging 8 points and 8.3 rebounds, but there is a belief around the league that he is capable of much more if healthy.

Brogdon’s Celtics tenure, meanwhile, ends after one strong year that was marred by a sour ending. After being acquired in a trade with the Pacers, he embraced his bench role and was named the league’s Sixth Man of the Year.

But he was slowed by a forearm strain during the conference finals against the Heat, missing one game and going just 1 for 16 from the field over his final four. In June, Brogdon was part of the initial three-team trade that would bring Porzingis to Boston, but the Clippers backed out because they did not have sufficient time to examine Brogdon’s injury.

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The Celtics pivoted and traded Smart to the Grizzlies in a different three-team deal, but Brogdon was reportedly frustrated by his inclusion in the initial trade, as well as news leaks about his health. The past few weeks, the Celtics’ social media accounts posted several videos of players working out at the Auerbach Center to prepare for the season, and Brogdon was the only one who never made an appearance.

The Celtics acquired the 2024 Warriors pick in the Smart deal, and have now parted ways with their own 2029 first-round choice. They could also owe the Spurs a 2028 pick swap, but otherwise have all of their future first-round choices along with a war chest of second-round picks. That capital could eventually be needed.

Although the Celtics have a fearsome starting five and can bring All-Defensive pick Derrick White, a star of last season’s playoffs, off the bench, there are some depth concerns. The regular rotation, for now, likely will include Sam Hauser, Payton Pritchard, Luke Kornet, and Oshae Brissett.

It would not be a dominant second unit, but the Celtics, who have been in contention for nearly a decade without taking the final step, are focused on the playoffs, when rotations are whittled down to seven or eight players. Their top six appear to be unmatched.

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The Celtics have signed veteran forward Wenyen Gabriel to a training camp deal, a league source confirmed. Gabriel, 26, averaged 5.5 points and 4.2 rebounds per game for the Lakers last season.


Adam Himmelsbach can be reached at adam.himmelsbach@globe.com. Follow him @adamhimmelsbach.