Jrue Holiday being sent from Celtics to Trail Blazers for Anfernee Simons and picks, AP source says

A person with knowledge of the details says Jrue Holiday is being traded by Boston to Portland, a year after helping the Celtics win the NBA championship
FILE - Boston Celtics' Jrue Holiday plays against the Washington Wizards during the first half of an NBA basketball game on April 6, 2025, in Boston. (AP Photo/Michael Dwyer, File)

Credit: AP

Credit: AP

FILE - Boston Celtics' Jrue Holiday plays against the Washington Wizards during the first half of an NBA basketball game on April 6, 2025, in Boston. (AP Photo/Michael Dwyer, File)

Jrue Holiday's acquisition from Portland helped spark the Boston Celtics to their NBA-record 18th championship last season.

Holiday is being sent back to the Trail Blazers by a Boston team that could now be in transition, a person with knowledge of the details said early Tuesday.

ESPN reported that the Celtics would get Anfernee Simons and two second-round draft picks from the Trail Blazers.

The departure of Holiday, who made his sixth career All-Defensive team selection in his first season in Boston, was confirmed to The Associated Press on condition of anonymity because the deal is not yet official.

Holiday was traded by the Milwaukee Bucks to Portland in September 2023 when the Bucks acquired perennial All-Star Damian Lillard. Holiday was then dealt days later to the Celtics, moving right into the starting lineup and eventually earning his second career title last June.

But the Celtics now have lost a second member of that starting lineup for at least part of next season, with All-NBA forward Jayson Tatum having surgery after an Achilles tendon injury in the loss to the New York Knicks in the Eastern Conference semifinals.

Simons could provide some of the scoring punch the Celtics have lost, having averaged 19.3 points last season after going for a career-best 22.6 per game in 2023-24.

But the Celtics will miss the defense and leadership that Holiday provided. The two-time Olympic gold medalist's scoring was down, though, with the 11.1 points he averaged last season his lowest since his rookie season in 2009-10, and more than eight points lower than the 19.3 he put up in 2022-23 with the Bucks, when he was an All-Star.

More than that, the Celtics were likely motivated to trade Holiday because of the $104.4 million owed to him over the remaining three seasons of the contract extension they gave him last year, on top of the huge deals for Tatum and Jaylen Brown.

Holiday, who helped the Bucks win the 2021 NBA title, has averaged 15.8 points in a 16-year career that also includes stints with Philadelphia and New Orleans.

Before trading Holiday, the Celtics’ payroll next year was slated to be around $225 million, creating a tax bill of almost $280 million. The combined potential $500 million total price tag would have been a league record.

The larger concern was that figure would have exceeded not only the projected luxury tax threshold of $155 million, but also the first penalty apron projected of around $196 million and the second penalty apron of around $208 million. Both barriers carry restrictive penalties including limits on trades and what teams are allowed to do via free agency.

And that was all on top of the lack of clarity on if the team's incoming ownership would want to keep paying such hefty penalties to maintain the current roster after agreeing to a purchase in March that is expected to have a final price of a minimum of $6.1 billion.

Trading Holiday suggests that new ownership wants at least some reduced spending before the start of next season. That's especially true with Tatum out for at least a huge portion of next season and Brown coming off knee surgery.

Tatum signed an NBA-record five-year, $314 million contract last July that will begin next season and pay him $54 million. Brown is playing under a five-year, $304 million deal that kicked in this past season. He will make $53 million next season. That is followed by Kristaps Porzingis ($30 million), Derrick White ($28 million) and Sam Hauser ($10 million).

Porzingis seemingly would be the next potential player the Celtics would consider moving, with $60 million total left in his deal before he is eligible for free agency again in the summer of 2026. But there are questions about his health after he missed a significant number of games in the second half of the regular season and was limited in the playoffs because of a nagging respiratory illness.

No matter which direction the Celtics decide to go, Boston president of basketball operations Brad Stevens acknowledged last month after his team was eliminated from the playoffs that it's unclear whether so-called championship windows are becoming smaller because of the current rules governing the salary cap.

“That’s a good question. I don’t know,” Stevens said. “I think certainly it is more challenging in certain circumstances for sure.”

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Portland Trail Blazers' Anfernee Simons plays during an NBA basketball game Monday, March 3, 2025, in Philadelphia. (AP Photo/Matt Slocum)

Credit: AP

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Credit: AP