Celtics Trade Jrue Holiday for Anfernee Simons in Blockbuster Deal

Celtics news update: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and draft picks. Shams Charania first reported the Jrue Holiday trade. Anfernee Simons, a sharpshooting guard, arrives in Boston under Brad Stevens’ plan. Coverage includes how Anfernee Simons fits, Celtics trade strategy, and Eastern Conference implications.

Trade Details: Holiday Goes to Portland, Simons to Boston

Celtics trade news broke on June 23, 2025, when ESPN’s Shams Charania reported that the Boston Celtics are sending veteran guard Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and draft picks. In fact, ESPN’s report confirms the deal. Notably, this deal involves only Jrue Holiday; his older brother, Lakers All-Star Drew Holiday, was never part of it. Fan searches for “Anfernee Simons trade” and similar terms have already surged, underscoring the interest. In concrete terms, the salary exchange works in Boston’s favor: Simons is on a two-year expiring deal (about $25.9M and $27.7M) while Holiday owed about $72M more over the next two seasons. This move saves roughly $40M in luxury tax costs in 2025-26 and keeps the Celtics about $18M under the punitive second apron.

• Boston Celtics get: 26-year-old Anfernee Simons, a high-volume scoring guard who shoots a lot of threes (nearly nine per game), on an expiring contract. Boston also acquires two future second-round picks. The trade clears about $72M of future salary (Holiday’s 2026-27 and 2027-28 salaries).
• Portland Trail Blazers get: 35-year-old Jrue Holiday, a veteran two-way guard (All-Defense team last season) with three years remaining on his deal (approx. $30M next season). Portland re-acquires the former Blazer to add championship experience to their roster. Holiday’s arrival is expected to boost Portland’s defense (they were a top-five defensive unit after mid-season).
• Search interest: Fans are already looking up Anfernee Simons and the trade. Even misspellings like “Anfernee Simmons” or “Afernee Simons” now lead to this news. Likewise, queries like “Jrue Holiday Blazers” or “TrailBlazers trade” will point to this deal.
• Boston’s move: The Jrue Holiday trade is already the biggest story in Celtics news, highlighting how seismic the roster changes are. It is expected to dominate offseason discussions in Boston.
• Team references: Media and fans use both “Trail Blazers” and “Trailblazers” to describe Portland in this coverage. This deal is one of Portland’s boldest Blazers trades, as the front office continues to remake the roster.

Jrue Holiday (#21, left) drives past Portland’s Jerami Grant (#9) during a game. Holiday, who won a championship with Boston in 2024, is headed back to Portland in the Anfernee Simons trade. Holiday, who won a championship with Boston in 2024, is now on the move again. In fact, Jrue Holiday has now been on five NBA teams: Philadelphia, New Orleans, Milwaukee, Boston, and Portland. For example, a Google search for “Jrue Holiday teams” would return this article, which lists all five of his franchises.

Celtics Perspective: How Anfernee Simons Fits in Boston

For Boston, Anfernee Simons offers immediate scoring punch. The 26-year-old guard averaged about 19.3 points last season on 42.6% shooting (36.3% from 3), and he once erupted for a 47-point game in Portland. In Coach Joe Mazzulla’s offense (which emphasizes spacing and shooting), Simons’ deep range is a big asset. With Kyrie Irving gone and Jayson Tatum injured, Simons can help fill the offensive gap. He isn’t as accomplished a defender or playmaker as Holiday, but his shooting and age (26) add youth to the roster. For Anfernee Simons, this trade immediately places him in the spotlight of Boston’s championship aspirations, with Celtics news outlets already analyzing his fit on the team. This also means every Eastern Conference opponent will have to game-plan for Anfernee Simons on Boston’s roster, a new element to their offense.

Simons’ contract status also looms large. He joins on an expiring deal ($25.9M for 2025-26 and $27.7M for 2026-27), making him a potential trade chip. As CelticsBlog notes, “Whether they’ll retain Simons — or trade him in the coming weeks — remains to be seen”. In short, the Celtics are taking a short-term risk (moving a proven veteran) for long-term flexibility (lower salary and draft assets). Simons’ performance will determine if he stays; Boston could extend him if he thrives or flip him for additional picks if not. For now, Boston’s front office – led by President Brad Stevens – is betting on Simons’ shooting to keep the team competitive. Indeed, insiders pointed out that Stevens “had to make a move to shed $$$” with Holiday’s massive contract, so this Simons deal lightens the financial load and frees roster space.

Brad Stevens’ Role and Celtics Plan

This trade is widely viewed as an initiative of Brad Stevens, Boston’s president of basketball operations. Stevens, recently named Executive of the Year, inherited a roster with a record-high payroll and had to plan for a long season without Tatum. ESPN’s Tim Bontemps noted that Stevens’ first offseason task is handling the team’s picks and finances, and this trade fits that narrative. By flipping Holiday’s contract, Stevens immediately moves Boston under the second tax apron, giving the team more flexibility on the luxury-tax scale. In Celtics news, management has stressed that the core will still center on Jaylen Brown (and a hopefully healthy Kristaps Porzingis next year). Yet this trade officially breaks up Boston’s 2024 championship lineup. It signals a pivot: Stevens is preserving winning windows for the future (e.g. 2026-27 when Tatum returns) by accumulating assets and cutting payroll now. Many analysts believe Stevens will stay active; with Simons coming in, the team might still explore deals around other key players during the offseason.

Portland Trail Blazers Perspective: Veteran Leadership

From Portland’s side, the trade is a chance to retool around Jrue Holiday’s veteran presence. Holiday originally came to Portland in the Damian Lillard trade and had the Blazers’ respect from his earlier stint. By re-acquiring Holiday, the Blazers add a two-way All-Defensive guard who can mentor young players. As Shams Charania tweeted, “Portland makes an aggressive move to re-acquire Holiday”. Holiday’s high basketball IQ and championship experience (with Milwaukee in 2021 and Boston in 2024) should aid the Blazers’ locker room, especially as they integrate their younger guards. However, Holiday’s large remaining salary (roughly $30M+ per season) suggests Portland also might flip him later if a bigger trade arises. For now, Blazers fans are simply getting back a familiar face and hope he can help stabilize the team’s defense. Trading away Simons does not hurt Portland’s cap – Simons’ contract is gone – which could help them target other free agents or deals.

Anfernee Simons: Future and Trade Rumors

The arrival of Anfernee Simons in Boston is generating its own buzz. As noted, Simons is on an expiring deal and will be an unrestricted free agent in 2026. CelticsBlog highlights that “whether they’ll retain Simons — or trade him in the coming weeks — remains to be seen”. Indeed, if Simons excels in Boston, the team could sign him long-term to replace Holiday’s offense. If not, they might deal him at the February trade deadline for more picks. Social media and forums are already abuzz with hashtags like #Celtics trade and #Simons, and even searches for “Anfernee Simmons” or “Afernee Simons” (common misspellings) will surface this story. For Simons himself, Boston represents a bigger stage and perhaps a chance to rebuild value. He joins Jaylen Brown, Kristaps Porzingis (expected back from injury), and sharpshooters like Malcolm Brogdon in a new-look backcourt. Whether Boston’s plans include Simons long-term or use him as a stepping stone, the trade rumors around him will continue until we see how the season shakes out.

Also check out The Best Nootropics for Focus & Memory: A Science-Backed Review

Eastern Conference Outlook

This blockbuster deal has shifted the Eastern Conference landscape. With the Celtics shedding a key veteran and possibly retooling around younger parts, other contenders may have a clearer path. The New York Knicks (who reached the Finals in 2024) and the Philadelphia 76ers (with MVP Joel Embiid) remain the frontrunners in the East. Boston’s window may narrow in 2026 if Tatum’s return is pushed to 2027. Eastern opponents must now account for Anfernee Simons when facing the Celtics, adding a new wrinkle to scouting reports. Additionally, teams like Milwaukee and Cleveland will watch how Boston integrates Simons in place of Holiday. In short, the Celtics are clearly banking on the long-term payoff of this Jrue Holiday trade, even if the near-term outlook is uncertain. The move amplifies urgency for other teams: with Boston temporarily weakened, rivals will double down on their own improvements. And Celtics fans will be watching all summer to see if Simons can help Boston stay in the title hunt.

Sources: Verified reports from ESPN and Sports Illustrated; salary analysis from Bobby Marks; local Celtics coverage (CelticsBlog).