Why the Boston Celtics are trading Jrue Holiday to Portland Trail Blazers

Following a frustrating postseason exit, made worse by Jayson Tatum’s Achilles injury, the Boston Celtics have caught the basketball world off guard by sending Jrue Holiday, a two-time NBA champ, to the Portland Trail Blazers.

In return, Boston brings in scoring guard Anfernee Simons along with a pair of future second-round picks. On paper, it's a deal that makes sense for both sides, but it also hints at a new chapter in Boston, as they look to retool their roster after falling short of back-to-back titles.

Holiday, a two-time NBA champion, played a pivotal role in Boston's 2024 title run, helping the franchise secure its record-breaking 18th championship banner.

This flurry of activity comes just a day after the NBA trade market exploded. The Kevin Durant blockbuster, which saw Jalen Green, Dillon Brooks, multiple second-rounders, and the No. 10 pick head to Phoenix in exchange for the veteran star, appears to have sparked a trade frenzy ahead of Game 7 of the Finals.

Barely 24 hours later, the Celtics followed suit, cutting ties with Holiday to ease the burden of looming second-apron luxury tax penalties. The move officially marks the end of Boston's 2024 title-winning core.

At the heart of the Holiday trade was Boston’s tightening financial noose. With Jayson Tatum ruled out and the Celtics eyeing another deep postseason push, the team found itself teetering on the edge of the NBA's dreaded second luxury tax apron, a zone that comes with brutal financial consequences.

Holiday's upcoming contract numbers, $32.4 million in 2025-26 and climbing, were simply too rich for a team already walking a salary cap tightrope.

By offloading his hefty deal to Portland, Boston clears roughly $40 million in tax liabilities, a major relief for a front office bracing for stiff penalties. Holiday was in the middle of a $134.4 million deal, and according to NBC, even the Dallas Mavericks considered using him as a trade chip, though absorbing his salary proved too tricky. ESPN's Bobby Marks had previously warned that the Celtics needed to slash around $20 million to get under the second apron, making this move all but inevitable.

But this wasn't just about the books. Holiday, now 35, posted career-low numbers since his rookie year — 11.1 points, 3.9 assists, and 4.3 rebounds, and his three-point shooting dipped to 35.3%. While his offensive output took a step back, his defensive prowess and playoff experience still carry serious weight.

In return, Boston picks up Anfernee Simons, a scoring guard who fits perfectly into Joe Mazzulla's perimeter-heavy system. Simons, 26, averaged nearly 20 points and knocked down close to 38% from beyond the arc last season. He also arrives on an expiring contract, giving the Celtics firepower without the financial strings attached.

Here's some of the quick reaction from the NBA world on the news:

Holiday is heading back to the team that briefly held his rights back in September 2023 — the Portland Trail Blazers. In that original three-team blockbuster involving Milwaukee, Phoenix, and Portland, the move was made to help the Bucks land Damian Lillard. But Holiday didn’t stay long in the Pacific Northwest; he was quickly flipped to Boston, where he became a key cog in the Celtics’ title run.

Now, the two-time All-Star and two-time NBA champion returns to Portland, bringing full circle a trade path that started nearly a year ago. For the Trail Blazers, this deal also helps clear up a logjam in the backcourt, moving on from Anfernee Simons, who had been competing for touches with the team's crop of rising young guards.