• Loading stock data...
Wednesday, August 6, 2025
Tuned In returns to NYC on September 16. Hear from the biggest names in sports media. Click here to get your spot

Celtics Trade Jrue Holiday Back to Portland As Salary Slashing Begins

The Celtics traded Holiday to the Trail Blazers two years after acquiring him from them in the first of what will likely be multiple trades to avoid the second apron. 

May 12, 2025; New York, New York, USA; Boston Celtics guard Jrue Holiday (4) dribbles in front of New York Knicks forward Mikal Bridges (25) in the second half during game four of the second round for the 2025 NBA Playoffs at Madison Square Garden.
Vincent Carchietta-Imagn Images

The Celtics’ teardown of their 2024 title team has officially begun. 

A day after the Thunder replaced Boston as the reigning NBA champions, the team traded defensive specialist Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks. The news was first reported by ESPN

The trade comes two years after the Celtics acquired Holiday from the Blazers for two first-round picks: Robert Williams III and Malcolm Brogden. 

By trading Holiday, the Celtics took the first step in avoiding a roughly $500 million payroll next season, including luxury taxes. 

Holiday, 35, is entering the second year of a four-year, $134 million extension he signed with the Celtics in 2024 that will pay $32 million next season and ends with a $37 million player option for the 2027–28 season. Considered one of the best defenders in the NBA, Holiday helped the Celtics win the 2024 Finals with his play against Mavericks star Luka Dončić. But he was going to be an expensive role player for the team as he gets older. Meanwhile, the team’s luxury tax penalties to retain him would hamper the ability to build around Tatum and Jaylen Brown for the coming seasons. Tatum will likely miss all of next season after tearing his Achilles against the Knicks in the playoffs. 

The deal saves Boston roughly $40 million in luxury taxes for next season as it gets the $72 million guaranteed to Holiday off its books. But it’s still $18 million over the dreaded second apron, which is why the team is exploring trades for center Kristaps Porzingis, who’s owed $30 million in the final year of his contract next year. Trading Porzingis could get the Celtics out of the second apron entirely. Sharpshooter Sam Hauser, who is about to start a four-year, $45 million extension, is another trade candidate. 

Simons made roughly $26 million for the 2024–25 season and is owed $27.7 million next season before becoming a free agent next summer. Just 26, he fits the Celtics timeline with Tatum (27) and Brown (28) better than Holiday. He’s extension eligible this summer for a three-year deal worth $105 million. But the team could wait until Simons starts playing for the Celtics before signing him to a new deal. The Celtics could be out of luxury tax entirely in two seasons based on the roster’s current construction and letting Simons’ deal expire before re-signing him helps keep it that way. 

Holiday is being traded before the NBA Board of Governors is scheduled to approve the sale of the team in July to Bill Chisholm, a Massachusetts native and longtime Celtics fan who’s buying the franchise for $6.1 billion. Chisholm said shortly after the purchase he planned to spend what was needed to keep the Celtics in contention. Despite multiple injuries to fellow Eastern Conference contenders including the Pacers and Bucks, the team decided to tear down its championship team anyway. 

My approach is to win and raise banners,” Chisholm previously told ESPN. “That’s in the near term and the long term. I’ve had a couple of sit-downs with [general manager] Brad [Stevens] and it’s been about aligning our goals, and extending the window of this team. The plans that [governor] Wyc [Grousbeck] and Brad have laid out make perfect sense to me.”

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Jul 28, 2025; Arlington, Texas, USA; Dallas Wings guard Paige Bueckers (5) and guard DiJonai Carrington (21) during the game between the Dallas Wings and the New York Liberty at College Park Center.

WNBA Trade Deadline Hits Ahead of Looming CBA Chaos

The trade deadline is Thursday at 3 p.m. ET.

Spurs Are Spending Big Now, but Can They Afford Their Future?

San Antonio traded for Fox in February ahead of the trade deadline.

Inked Under Anesthesia: Athletes Getting $50,000 Tattoos

High-end studios, elite artist teams, and hours under anesthesia.
Steve Pagliuca

Boston Group Has Deal to Buy Sun For WNBA-Record $325 Million

The league office cautioned that any Boston move was subject to approval.

Featured Today

Coco Gauff at New York Liberty

How the New York Liberty Became the Hottest Ticket in Town

Once banished to the burbs, the Libs are now Brooklyn’s marquee attraction.
Las Vegas sign
July 29, 2025

College Sports Embracing Vegas After Years of Cold Shoulder

The Big Ten became the latest newcomer to Sin City.
2000, Jupiter, FL, USA; FILE PHOTO; Montreal Expos pitcher Hideki Irabu in action on the mound against the New York Mets at Roger Dean Stadium during Spring Training
July 28, 2025

Dead Sports Franchises Are Alive and Well on Twitter

The Expos, Sonics, and Whalers have active social media accounts.
Limited Hype
July 27, 2025

Sneaker Reselling Was Once Easy Money. Success Is Now Complicated

Vendors need to evolve what they’re selling and how they do it.
Mar 24, 2025; Phoenix, Arizona, USA; Milwaukee Bucks injured guard Damian Lillard against the Phoenix Suns at Footprint Center.

Damian Lillard and All the NBA Players Taking College GM Roles

The All-Star was named general manager of Weber State men’s basketball Saturday.
Leo Messi
exclusive
August 1, 2025

MLS Commissioner Don Garber Defends Messi Suspension

Messi was punished for skipping the MLS All-Star Game.
August 2, 2025

Luka Dončić Signs 3-Year Lakers Extension On 1st Day Of Eligibility 

Dončić can opt out after two seasons and sign a record deal.
Sponsored

Game On: Portfolio Players Stories, Brought to You by E*TRADE from Morgan Stanley

Dealmaker Jeffrey Kaplan maps the evolution of sports as an asset class
August 1, 2025

Micah Parsons Requests Trade From Cowboys As Contract Talks Stall

The defensive end has been seeking a new contract.
McLaurin
August 1, 2025

Terry McLaurin Asks Out of Washington Amid Contract Standoff

McLaurin is in the final year of a three-year, $68 million contract. 
July 31, 2025

Mikal Bridges Takes $6M Discount to Help Knicks Avoid Second Apron

Bridges agreed to a four-year, $150 million extension Thursday.
Apr 25, 2025; Minneapolis, Minnesota, USA; Los Angeles Lakers guard Luka Doncic (77) looks on against the Minnesota Timberwolves in the first half during game three of first round for the 2024 NBA Playoffs at Target Center.
July 31, 2025

Luka Dončić Eligible to Sign $229M Extension Saturday

Dončić can sign a four-year, $229 million extension on Aug. 2.