Grading the NBA Trade: Boston Celtics Send Out Jrue Holiday, Receive Anfernee Simons From Portland Trail Blazers

Just one day after the conclusion of the 2024-25 NBA season and with the clock nearing midnight on the East Coast, the Boston Celtics began their monumental offseason with a cross-country trade of Jrue Holiday to the Portland Trail Blazers. In return, they’ll welcome Anfernee Simons, a talented guard who will bring a scoring punch but hasn’t yet been relied upon on the big stage in his seven-year career.

What does this mean for the Celtics’ offseason plans, and does this signal a win-now move for the Trail Blazers following a promising finish to last season?

Breaking Down the Jrue Holiday-Anfernee Simons Trade Details

The trade was first reported by ESPN’s Shams Charania on X.

“BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN,” Charania posted.

BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT

— Shams Charania (@ShamsCharania) June 24, 2025

The complete package includes Portland’s 2031 second-round pick and the New York Knicks’ 2030 second-round pick that the Trail Blazers had previously acquired. Let’s grade both sides of the deal, beginning with the Celtics, who are sending out an aging player for a youthful yet experienced scorer.

Boston Celtics Analysis

After being bounced from the second round of the playoffs and facing the second apron of the luxury tax, the entire league knew that the Celtics were heading into an offseason that would be full of intriguing decisions and potentially vast changes.

Add in that superstar forward Jayson Tatum tore his Achilles in the second-round series against New York, potentially sidelining him for the entirety of the 2025-26 season, and general manager Brad Stevens had work to do.

It didn’t take but a day after the NBA Finals finished that the first domino has fallen with Holiday heading out the door.

Boston acquired Holiday from the same Trail Blazers’ front office ahead of the 2023-24 season. He proved to be the final piece of their championship roster that claimed the franchise’s league-leading 18th title and their first since 2008. Holiday’s hounding, anticipatory defense, and championship-level maturity (he also won a title with the Milwaukee Bucks in 2021) were vital for the Celtics throughout their run.

Prior to the playoffs in 2024, Boston signed Holiday to a four-year, $134.4 million deal, presumably to finish his career as a Celtic. But with $67.2 million still to be paid over the next two seasons and with Holiday posting his lowest scoring output since his rookie season, Stevens decided it was time to get out of the Holiday business and his increasingly expensive contract.

In addition to easing the luxury tax bill, which comes out to saving a projected $40 million in tax money for the 2025-26 season, the Celtics received a player who has scored 19 or more points per game in each of the last three seasons.

Simon’s contract is also favorable, as he has just one more year remaining on his four-year, $100 million contract signed in 2022. After next season, if the Celtics decide not to re-sign him, they’ll have shed and be completely freed from Holiday’s remaining salary that would’ve hung over their head.

If Boston does decide to re-sign Simons, they can do it on their terms and with a number that they know they can manage moving forward. Contract and luxury tax details aside, which comes out as a resounding victory for Boston, the player-for-player swap is also excellent business for the Celtics.

While Holiday is one of the best defenders in the NBA, fellow guard Derrick White is also an All-Defensive team-caliber guard who can step in and take the challenge in his absence. Holiday also had his worst 3-point shooting season since 2019-2020 and didn’t always bring much to the table offensively.

Enter Simons, who has been an explosive, eruptive scorer with the ball in his hands the last two seasons in averaging a career-high 22.6 points per game two seasons ago and 19.3 points last season. A volume shooter from deep, he knocked down 3.1 of his 8.5 attempts per game last season, good for 36.3%.

It’s worth noting that he can also play off the ball as he did in a combo guard role for the Blazers in 2022-23, Damian Lillard’s last season with the team. Starting 62 games alongside Lillard, Simons averaged 21.1 points and was a prime candidate for the Most Improved Player of the Year award.

With Tatum sidelined for potentially the year, Simons adds a much-needed scoring punch and will give the Celtics’ front office a year to make a decision on whether or not to let him walk in free agency and have added cap space freedom or sign him long term.

Oh, and they also managed to receive two second-round picks in the deal from a Portland team that has had that pick fall in the early second-round range in recent years.

In all sides of the deal, on court, luxury tax, draft picks, this is a win for Boston.

Celtics Grade: B+

Portland Trail Blazers Analysis

Two summers ago, general manager Joe Cronin dealt Portland’s beloved superstar and franchise cornerstone Lillard in exchange for Holiday, Deandre Ayton, Toumani Camara, and draft compensation. Now, in the wee hours of June 24, Cronin has traded a borderline star guard in Simons for Holiday again.

But this time, the vibe is a little different around Portland.

A little after the calendar turned to 2025, the Trail Blazers finally found their identity under head coach Chauncey Billups in his fourth year at the helm: defense.

From Jan. 19 to Feb. 6, a span in which the Trail Blazers won 10 of 11 games, they held opponents to just 102.1 points per game. That would’ve ranked first in the NBA across the entire season by over three points.

Considering that newfound aspect of the team and what Holiday brings to the table, is this setting up for a different result than what Cronin pulled off in 2023, when he rerouted Holiday to the Celtics just three days later? Certainly could be. It’s unlikely that many teams, if any, would be comfortable taking on Holiday’s salary outside of the Trail Blazers, assuming they view him as a keeper.

MORE: PFSN NBA Mock Draft Simulator With Trades!

In that case, he’d immediately step in as the top perimeter defender on the team. The point of attack had been a weak spot for Portland’s defense, as Simons and shooting guard Shaedon Sharpe are below-average on-ball defenders.

But with Holiday in the fold, they’d potentially have elite defenders at all three levels: the point of attack (Holiday), the wing (Camara), and at the rim (7’2″ center Donovan Clingan).

If this does prove to be a move in which the Trail Blazers are pushing their chips in, the question arises of what other moves could be made. Oft-injured center Robert Williams III is a menace defensively when healthy but is the third center on Portland’s roster behind Clingan and Ayton. He could potentially be dealt for another contributing player.

Jerami Grant is a similar case, as he doesn’t quite fit the timeline of the current roster.

There is talent within the team already if no other moves are to be made. Scoot Henderson is entering his third year after being selected No. 3 overall in 2023 and, despite taking a step back in his sophomore season, still has all the potential that made him a high draft pick. Sharpe is ultra-athletic and has a terrific 3-point shot. Deni Avdija blossomed last season, notching career highs in points, rebounds, and assists.

But where exactly does the addition of Holiday to that mix leave the Trail Blazers in the stacked Western Conference?

In reality, still far outside of contending status, to date. There are still other moves that could be made that could either bolster or undermine the team’s chances of winning next season.

However, regarding this trade, Cronin identified Simons as a moveable piece and acquired a player in Holiday who fits with the roster’s identity and could be a mentor for the team’s young guards.

Trail Blazers Grade: B-