In the first major transaction to shake the league since the NBA Finals concluded, a blockbuster trade between the Boston Celtics and Portland Trail Blazers involving two-time NBA champion Jrue Holiday had an indirect, yet notable, connection to the New York Knicks.
The deal, widely reported by sources including ESPN’s Shams Charania, saw the Boston Celtics send veteran guard Jrue Holiday to Portland. In return, Boston acquired guard Anfernee Simons and two future second-round draft picks from the Trail Blazers.
The Knicks Pick’s Journey
Intriguingly for Knicks fans, one of those second-round selections heading to Boston originated in New York. According to reporting, including from Jake Fischer of The Stein Line, the pick is a 2030 second-round choice.
This pick previously belonged to the Knicks but was sent to Portland as part of a transaction during last year’s NBA Draft. In that deal, the Knicks moved up to the 34th overall selection, which they used to draft Marquette alum Tyler Kolek. To complete the trade with Portland, the Knicks also included second-round picks in 2027 and 2029, along with the draft rights to Spanish prospect Dani Diez. Now, one piece of that package from the Blazers is back on the East Coast, landing with an Atlantic Division rival.
Celtics’ Financial Maneuvering
While acquiring scoring depth like Anfernee Simons is valuable, the primary driver for the Celtics in trading Holiday appears to be significant financial savings. Reports indicate the move is designed to create substantial salary cap relief and help Boston dip below the NBA’s restrictive second luxury tax apron.
Trading Holiday and the remaining salary on his contract is projected to save the Celtics tens of millions – potentially around $40 million in combined salary and tax according to some estimates – as they navigate an offseason reportedly focused on cost management. This move, followed quickly by another major trade sending center Kristaps Porzingis to Atlanta, is part of a broader effort to drastically reduce future tax penalties, potentially saving the franchise around $180 million in taxes when combined with other recent transactions aimed at getting below the second apron.
Post-Playoff Shakeup
These trades come on the heels of a disappointing end to the Celtics’ season, where their title defense was halted by the New York Knicks in a six-game second-round series victory for New York – the Knicks’ first trip to the Eastern Conference Finals since 2000. Adding urgency to Boston’s situation is the reported Achilles injury sustained by star forward Jayson Tatum during the playoffs, potentially sidelining him for a significant portion, if not all, of the upcoming season. Simons’ scoring ability could be critical in Tatum’s absence. The team is also reportedly operating under new majority ownership, which may influence financial strategies.
What It Means for Portland
For the Portland Trail Blazers, receiving Jrue Holiday brings an accomplished, veteran defensive presence and two-time NBA champion to their roster. Holiday is widely regarded as one of the best perimeter defenders of his generation and a valuable leader.
However, there are conflicting reports regarding Portland’s plans for the 35-year-old guard. While some speculation suggests he could be re-routed in another trade – mirroring his brief stint in Portland after the 2023 Damian Lillard trade before being sent to Boston – other reports indicate the Blazers intend to keep him to provide veteran leadership and defensive help, particularly for young guard Scoot Henderson, and integrate him into their plans to try and improve in the Western Conference.
This Holiday trade was among the first significant transactions to shake the league shortly after the NBA Finals concluded, setting a tone for what is expected to be an eventful offseason already featuring other major moves like Kyrie Irving re-signing, the Pelicans trading CJ McCollum, and the Suns dealing Kevin Durant.
So while the New York Knicks weren’t directly involved in the Holiday-Simons exchange, a small piece of their future draft capital is now headed to their Atlantic Division rivals as part of Boston’s significant roster and financial shakeup following their season-ending playoff loss to… the Knicks.
