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Jrue Holiday is an intriguing but unlikely trade target for Celtics

In what’ll become an aggressive bidding war, it’s hard to imagine the Celtics winning the race for Jrue Holiday. The prospect of adding one of the best point guards in the league could, however, solidify another championship roster.

Milwaukee Bucks v Miami Heat - Game Four Photo by Megan Briggs/Getty Images

Marcus Smart and Jrue Holiday remain intertwined, for their battle in the 2022 playoffs that featured a memorable play where Holiday threw the ball off Smart out-of-bounds to secure Game 5, for their shared community work and for their similar playing styles. No rival more closely resembled the everlasting hustle style that Smart embodied more than Holiday.

Following the Damian Lillard-for-Jrue Holiday trade on Wednesday, the Celtics now have a chance to replace the departed Smart with his basketball doppelganger. Holiday looks like the player the Celtics need to address a lack of point guard playmaking, intangible and physical concerns remaining on a roster that should otherwise pull ahead of the field given their talent level. He’d make Milwaukee, Denver and the Lakers say, “uh oh.”

He’ll come at an enormous cost though, both in salary, given his one-year deal needing an extension, and in assets, as Portland prepares to assess numerous offers by contenders ahead of next week. Adam Himmelsbach reported Boston will join other teams inquiring about Holiday, as the team assesses the fallout from the near Malcolm Brogdon trade to LA, which Brad Stevens admitted to The Boston Globe left the guard upset.

Brogdon enters training camp healthy, and while The Globe reported that the team won’t actively shop Brogdon, an opportunity like this makes a deal more than worth exploring. The problem? Brogdon’s $22.5 million contract alone doesn’t get Boston there, needing north of another $10 million to match Holiday’s $37 million salary. That makes Holiday an unaffordable luxury, albeit an extremely difficult player to pass up on.

There’s a path if the team decided to part ways with Derrick White or Al Horford, but both players feel far too central to Boston’s defensive backbone and veteran leadership. Robert Williams III could go with Brogdon, forfeiting a ceiling-raiser and important depth at center behind injury-prone Kristaps Porzingis and aging Horford, along with the best overall defensive player on the roster.

Miami Heat (123) Vs. Boston Celtics (116) At TD Garden (Game 1) Photo by Jim Davis/The Boston Globe via Getty Images

It’d shift the team’s reliance on Brogdon and Williams III toward Holiday — a far better player than both. That gives the Celtics one slam dunk at a championship before financial concerns emerge, and gets ahead on future decisions regarding Brogdon and Williams. Though not quite Kevin Durant, he’d provide a similar boost. A Celtics’ Holiday trade also keeps him away from rivals like Miami and Philadelphia, while acquiring him for the battle ahead against his former Bucks.

Holiday will turn 33 this season and looking for an extension. His agent Jason Glushon represents several current and former Celtics, including Smart, and just negotiated the largest deal in NBA history for Jaylen Brown. He won’t offer Boston a discount. The 140% salary increase in the new CBA allows Holiday to earn as much as $50 million in the starting salary on his next deal, beginning in 2024-25. Boston can’t stack five smaller salaries to match Holiday, since Svi Mykhailiuk and other signings don’t become trade-eligible until December (although a sign-and-trade of Blake Griffin is possible).

Holiday’s contract could increase to over $60 million by the end of a four-year extension when Holiday turns 37. That’s life going all in. The Bucks just assumed similar risk in Lillard, but faced pressure from Giannis Antetokounmpo who will be looking for a new deal soon, too. So, they acquired one of the best players in the sport.

There’s virtue for the Celtics making this kind of move ahead of a critical year. It’s worth wondering if Holiday makes the most sense for consolidation without flexibility. The Celtics would likely have to trade Brown, Holiday or Porzingis in short order ahead of Jayson Tatum’s super max extension. Derrick White will also stand to earn nearly $28 million in Year One of his potential extension, while Payton Pritchard’s next contract would probably fall closer to the mid-level exception.

Trades become harder for impending second apron teams like Boston in 2024, with some argument for locking in the highest team salary possible before those penalties hit with bad deals becoming worse in a less flexible market. Milwaukee and Phoenix made their choice. Boston hinted at theirs by trading Porzingis.

“We want to win,” Stevens told CelticsBlog/CLNS Media when asked why Boston added another massive salary in this new collective bargaining agreement environment.

Minimizing White becomes the hardest part in all of this. White deserves to start and blossom after one of the more encouraging seasons by a role player in recent Celtics history. At times, White looked like an All-Star, capping his campaign with a historic Game 6 putback that shouldn’t go forgotten despite what followed. He shot nearly 40% from three on over 500 attempts, made an All-Defense team, added muscle this summer and rarely makes the wrong decision. Starting him emboldened that performance.

Pairing Holiday and White makes some sense but pivots the Celtics back toward smaller lineups. Brogdon, reportedly healthy entering camp, would depart as the steadiest scorer and shooter of the three guards. Losing Williams III would damage Boston’s lineup flexibility, especially after letting Grant Williams go. Adding Holiday might make for a net increase in physicality.

It’s truly one of the tougher trade decisions I’ve considered covering this team. Something’s missing intangibly in this locker room that’s allowed one of the most talented teams in the league to fall short over the past two seasons. Holiday could prove to be that missing piece, but this decision arrives before the team can realize whether Porzingis solves what went wrong last year.

“We have a lot of flexibility. We can play big and small. I like obviously our experienced guys that everybody knows their name. I like those guys a lot, they can help lead it,” Stevens told the Globe. “But I like a lot of our younger guys and what they can ultimately become. We may not see that game to game right now, but I’ve been impressed the way they’ve been working.”

There’s risk in standing pat. Holiday could bolster 76ers and Heat teams searching for their own next identities following James Harden’s trade request and Miami’s failed Lillard pursuit. That’s not a reason to make a deal though, and with training camp ahead next week — this trade talk sounds too good to be true.

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