When Jayson Tatum suffered a season-ending Achilles injury that will almost certainly cost him most of the 2025-26 NBA season, it called the very future of the Boston Celtics into question.

Would the team keep their expensive core together without a chance to make the NBA Finals for the second year in a row? Or would they look to move off of some more expensive, older options to get younger and cheaper moving forward?

Well, on Monday, June 23, fans got at least part of their answer, with the Celtics trading Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, as initially reported by ESPN's Shams Charania.

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Looking at the numbers, the decision to move on from Holiday was always a possibility, as he was on the books for $32.4 million and at 35 years old, is unquestionably a depreciating asset. But trading him away for Simons, a one-way scoring guard on an expiring contract, says a lot about why this deal was done.

According to Bobby Marks, this deal saves the Celtics $40 million against the cap in 2025-26, with $72 million taken off the books from 2026-28. Boston can take a financial step back in 2025-26 while adding a volume scorer to a team that just lost one, improving their ceiling a bit versus where Holiday falls at this point in his career, and the team will have far more financial optionality in the future, which could including keeping to moving on from Simons, depending on how his season shakes out.

With Tatum out of action, the 2025-26 season was always going to be a bit of a weird year for the Celtics, but with Holiday on the move and his replacement a 26-year-old who averaged 20.7 points per game over the last three seasons, Boston found a surprising way to keep things interesting heading into a bridge year.