Portland has Ja Morant, Damian Lillard returning from a torn Achilles, Scoot Henderson and Jrue Holiday. That is four point guards. There is one basketball.
Everyone has decided Holiday is the one who goes. Portland has been saying otherwise.
The Contract, Correctly Stated
The figure floating around is two years and $72 million. That is technically accurate and functionally misleading.
Holiday is owed $34.8 million guaranteed this season. The 2027-28 salary of $37.2 million is a player option with a June 2027 deadline. Only the $34.8 million is actually committed money, which makes him considerably more tradable than the headline number suggests.
The deal traces back to a four-year, $134.4 million veteran extension he signed with Boston in April 2024.
He Is 36 and Still Good
Holiday turned 36 in June and is entering his 18th season. Last year he played 53 games with 51 starts, averaging 16.3 points, 4.6 rebounds and 6.1 assists in 29.4 minutes while shooting 45.1 percent from the field and 37.8 percent from three.
In five playoff games against San Antonio he averaged 16.4 points, 5.4 rebounds and 7.2 assists on 38.4 minutes a night.
He scored a season-high 35 against Memphis on March 4, passed 17,000 career points two days later, and won the Maurice Lucas Award.
The availability is the issue. A right calf strain on Nov. 14 cost him 27 straight games, and he has not played more than 69 games in a season since 2022-23.
Correcting the Trade That Brought Him There
The widely repeated version says Portland sent Anfernee Simons and two second-round picks to Boston. That was the deal as originally agreed in late June 2025.
After Portland reviewed Holiday’s medicals, the two seconds were removed. The trade that actually completed on July 7, 2025 was a straight one-for-one: Holiday for Simons. Boston received nothing else.
What Portland Has Actually Said
This is where the September rumor mill runs thin. There is no hard insider reporting on Holiday from this month. Everything dated September is fan-site opinion.
The last real reporting is from late June and July. Marc Stein and Jake Fischer wrote on June 30 that Portland had been signaling to rival teams it plans to keep him, while conceding it could be posturing and calling him the most logical outgoing salary after the Jerami Grant trade.
Jason Quick of The Athletic reported no urgency and a plan to play Holiday at shooting guard and small forward. On July 1, Quick reported that new head coach Micah Nori flew to Los Angeles to meet Holiday and assure him he is in the plans.
Holiday Wants to Stay
He told Joe Freeman of The Oregonian in May exactly where he stands.
“I hope so. I don’t like being traded and moved and stuff,” Holiday said. “I like being a part of something and building with the team.”
The Market Is Thinner Than You Think
Cleveland considered Holiday at the February 2026 deadline before landing James Harden instead. That is past interest, not current interest. Phoenix and Orlando appear in columns as hypotheticals, not as reported suitors.
A 36-year-old guard with a $34.8 million salary and a durability history is a luxury purchase for a contender, not a pivot piece. Portland can keep him, play him off the ball as Quick reported, and revisit it at the deadline when a playoff team gets desperate.
That is almost certainly what happens.
A longtime sports reporter, Carlos Garcia has written about some of the biggest and most notable athletic events of the last 5 years. He has been credentialed to cover MLS, NBA and MLB games all over the United States. His work has been published on Fox Sports, Bleacher Report, AOL and the Washington Post.