Holiday had been a valuable contributor for the Celtics in his two years with the team, playing a big role in helping them to their championship in 2024. He averaged 11.1 points, 4.3 rebounds, 3.9 assists and 1.1 steals in 62 games this past season while playing a versatile defensive role for the side.
However, the future for the Celtics was thrown for a loop after their shock defeat to the Knicks, losing superstar forward Jayson Tatum to a torn Achilles in the process.
Now, without Tatum and already far above the second tax apron, the team decided to switch things up to prioritize the future over the present. With the decision to trade Holiday, the Celtics move off the 35-year-old’s $32.4 million cap hit for the 2025-26 season. He’s also set to make $34.8 million in the 2026-27 campaign before getting a $37.2 million player option for 2027-28.
A two-time NBA champ and 16-year veteran, Holiday brings some valuable experience to a Trail Blazers team that previously dealt him after acquiring the guard from the Milwaukee Bucks in the 2023 Damian Lillard trade. He’ll now join his fifth NBA franchise after stints with the New Orleans Pelicans, Philadelphia 76ers, Milwaukee Bucks and the Celtics.
Meanwhile, according to Charania, Boston remains engaged in trade talks surrounding multiple key players on the roster.
Until then, the Celtics add a promising young player about to enter his prime and on a cheaper, shorter-term deal than Holiday. Simons, 26, is set to make $27 million next season before hitting free agency. He is, however, extension-eligible as well.
Dealing away Holiday for Simons gave the Celtics a projected $40 million in tax savings for 2025-26, per ESPN’s Bobby Marks, and got the team $18 million below the second apron.
And as long as Simons is with Boston, his 19.3 points, 2.7 rebounds and 4.8 assists on 42.6/36.3/90.2 per cent shooting splits through 70 games last season will be a welcome addition to a Celtics roster that’s looking to fill a Tatum-sized hole until the six-time all-star returns.
Meanwhile, his high-volume three-point shooting will also fit right in with a Boston squad that took and made more long-distance shots than any other team in the league last season. Simons is one of only six players with an average of three-plus makes from beyond the arc in each of the last three seasons.
As for the picks the Celtics will also receive, the second-rounders will be via the New York Knicks (2030) and Portland’s own 2031 selection, per NBA insider Jake Fischer.
