Where Does the Jrue Holiday Trade Leave the Celtics?

The Celtics returned Holiday to the franchise from which they initially received him via trade back in October of 2023. In exchange for the two-time NBA champion, Boston receives a proven offensive talent on an expiring contract.

The Celtics, as expected, are breaking up their 2024 championship-winning core, and may not be finished. Boston has already traded Kristaps Porzingis to Atlanta for Georges Niang and a swap of second-round picks. Jaylen Brown continues to garner “significant interest” in the wake of the Holiday and Porzingis deals.

The motivation of the Porzingis trade is clear: Boston is beneath the second apron, having achieved the payroll cuts it was in desperate search of. Holiday’s departure achieves a similar goal, but the acquisition of Anfernee Simons makes the trade far more interesting. 

WHAT LOSING JRUE HOLIDAY MEANS

Boston sought Jrue Holiday’s talents to get it over the hump in its pursuit of an 18th championship. Holiday helped Boston do just that, serving as a defensive anchor and pairing seamlessly with Derrick White to form a stellar two-way backcourt.

Holiday’s poise in big moments was his greatest asset as a Celtic, and it paid dividends in the 2024 playoffs. His 26-point double-double in Game 2 of the NBA Finals gave Boston a 2-0 lead in its eventual series win. In the Eastern Conference Finals, Holiday was even better. His 18.5 points per game made him the team’s third-leading scorer behind Jayson Tatum and Jaylen Brown.

Holiday’s late heroics in Game 3 of that series will not be forgotten. The then-33-year-old scored five points in 39 seconds to give Boston its first lead in 36 minutes. He sealed the victory with a steal on Andrew Nembhard in the waning seconds.

Despite being best known for defense, Holiday quickly took to the Joe Mazzulla three-point avalanche offense. His 59.7 FG% on corner threes in 2023-24 was by far the highest in the league. 

Holiday’s efficiency sharply regressed this past season—his 35.5 3P% was the lowest since 2018-19—but his commitment to the approach did not waver. 51.4 percent of Holiday’s shots came from beyond the arc, the most of any Celtics starter besides Derrick White.

With that regression in mind, perhaps the most notable thing Boston loses by trading Holiday is his contract. The Celtics owed the 35-year-old Holiday $34.8 million AAV through 2027-28. Sending Holiday to Portland gets Boston out of a lengthy, expensive commitment to an aging player.

Holiday’s talents are still very much valuable. That much is proven by the price the Trail Blazers paid to get him. Despite a significant return package, the Celtics will miss Holiday’s presence as a defensive anchor.

The Celtics would not have won the 2024 title without Holiday. For that, he will always be remembered fondly in Boston.

WHAT ANFERNEE SIMONS GIVES THE CELTICS

As far as possible returns for Jrue Holiday, Anfernee Simons is much better than expected. 

Simons brings a wealth of offensive talent to the Celtics. While not an overly gifted scorer, he is more than capable, scoring above 17.0 PPG in four straight seasons. Simons boasts a career 38.1 3P%, suggesting he could thrive in the Mazzulla offense. He has shown All-Star potential in the past and could recapture that after a down year in Portland.

Simons’ defense leaves much to be desired, however. He ranked in the bottom 28th percentile in opponents’ points per possession (+2.5) in 2024-25. In 2023-24, the most prolific offensive year of his career, he was in the bottom 11th percentile (+5.3).

Simons on/off rating of -6.1 in 2024-25 ranked in the bottom 23rd percentile. That figure is quite alarming considering he was Portland’s top scorer.

Like Holiday, Simons’ most notable asset from the Celtics’ point of view is his contract. The 26-year-old is on an expiring contract worth $27.7 million in 2025-26, making him a valuable trade asset. Now that Boston is below the second apron and can aggregate contracts in trades, Simons could be moved before the season or at the deadline for a sizable package.

Simons has the offensive talent to be a difference maker, but his advanced metrics and lack of defensive talent are cause for concern. It’s more likely that he is a one-year rental than part of Boston’s long-term plans.

GRADING THE DEAL FOR BOSTON

Before the trade, it was hard to envision Boston moving Holiday for a significant return without attaching major draft capital. Despite that, Brad Stevens found a way to acquire a young, talented player on an expiring deal without losing draft picks.

At best, Anfernee Simons could thrive in Joe Mazzulla’s offense and help Jaylen Brown and Derrick White lead a competitive Celtics group in the absence of Jayson Tatum. At worst, Simons is a fun one-year rental for Boston, which is in a gap year without its best player.

Holiday’s physical costing the Celtics draft picks stings, but Brad Stevens did all he could to maximize the aging guard’s value.

Grade: B+

CONCLUSION

Together, the Kristaps Porzingis and Jrue Holiday trades give the Celtics with much-desired salary relief without having to sacrifice additional assets. At the same time, they deprive Boston of two championship pieces.

Both trades mark an unfortunate but necessary divorce and are a powerful reminder of the reality of the NBA’s second apron.