Boston is still undergoing an offseason makeover, but this time, valuable draft assets are being traded in addition to players. Fans and the media are reacting to a shocking development as the Celtics complete the Jrue Holiday trade with Portland: Boston is losing draft picks in addition to a seasoned guard.

Original Deal vs. Final Outcome

NBA insider Shams Charania said in late June that Boston had reached an agreement to move Jrue Holiday to Portland in return for Anfernee Simons and two Trail Blazers future second-round choices. At that point, it appeared to be a straightforward asset grab and salary exchange.

However, the official version on Monday had a different tone: Boston traded Holiday for Simons upfront, with no picks returning. The deal excluded all of Boston’s draft capital, which is a strange decision that has caused several leaguers to take notice.

Why the Picks Vanished

The Celtics’ management required as much freedom as possible under the NBA’s second luxury tax apron because of their soaring salary and the impending effects of Jayson Tatum’s Achilles injury. Boston saved more money and offloaded more cash more quickly by cutting incoming draft picks, which makes more sense for a team looking to rebuild cap space.

However, other analysts contend that Boston may have lost out on important draft prospects by prioritizing pay relief above asset return, which could have weakened their long-term outlook.

Celtics Get: Simons, But Lose Assets

Gain: A youthful, accurate shooter with an expiring contract, Anfernee Simons (19.3 PPG on 38% from deep last season) is perfect for cap maneuvering.

Loss: There will be fewer trade chips and draft alternatives going forward due to the lack of second-round selections.

Cap Relief: Boston reduces next year’s tax exposure by an estimated $40 million by offloading Holiday’s final three-year, $100+ million commitment.

Big Picture: Cap Cleansing Over Continuity

Financial breathing room was obviously a top priority for Boston’s front team. With the departure of Holiday and Kristaps Porziņģ (pending a separate three-team trade), the Celtics are cutting their total salary and luxury tax liabilities by over $64 million, which could free up a significant amount of mid-level and exception room.

This change suggests that Boston will adopt a mini-rebuild, accumulating cap flexibility instead of immediate depth, particularly during the year after Tatum’s injury.

Reaction from Media & Fans

Grades: Boston received a B+ from SI, which acknowledged the need for finance but lamented the loss of draft assets.

Reddit users expressed their disapproval of the move and lamented the loss of picks, affecting the fan reaction to be critical.

The view was shared by Yahoo Sports, which noted Boston as a top “loser” in offseason activity because of what they gave up and said, “They got rid of Jrue Holiday’s massive contract.”

What Comes Next

Roster Reset: Now that the cap sheet is clear, Boston may look into midseason trades or free agent acquisitions, probably aiming for G-League players, veterans, or possibly a blockbuster if Tatum is healthy.

Draft Dependency: The Celtics will have to rely on player development or trades in the absence of picks. Instead of drafting, they might have to deal for their next influx of talent.

Tony Bradley? In order to rebuild, some speculate that Boston may bundle elsewhere—possibly Derrick White or Jaylen Brown—in future transactions.

Final Take

Boston is prepared to exchange draft assets for roster flexibility and payroll relief, as evidenced by the Jrue Holiday–Anfernee Simons transaction. Even if it makes sense fiscally, especially now that Tatum is out, it eliminates the upside of future drafts.

For Celtics supporters, this is an indication that the team is making a change and prioritizing financial stability above immediate depth. It would make sense if the goal is to replace as soon as roster and salary health permit. Boston faces stagnation if it doesn’t.

With no selections returning and a large amount of cap space available, everyone will be watching Boston’s next moves, whether they are daring trades or smart acquisitions. From championship contender to cap-savvy architect, the story is changing. What kind of foundation are they going to lay?