Goodbye Holiday: Boston Celtics start to dismantle championship team

It’s not that the Finals needed to end for the NBA’s signing machine It’s not as if the NBA needed to wait for the Finals to end before trade season began – see Desmond Bane and Kevin Durant – but now, with the curtain officially down, there’s no need for subtlety anymore. With the playoffs over, it’s draft and trade time, and the Boston Celtics are the first to jump into the action.

Celtics freshen the roster

The franchise that lifted the trophy a year ago and entered this past season as favorites to repeat has just fired the starting gun on dismantling the roster that delivered its historic 18th title. Jrue Holiday is on his way to the Portland Trail Blazers in a trade that brings Anfernee Simons and two second-round draft picks to Boston.

Holiday is returning to Portland, where he spent a brief – and entirely symbolic – stint in the summer of 2023. He was initially traded there from Milwaukee as part of the Damian Lillard deal, only for Boston to swoop in days later and make him a cornerstone of a starting five that steamrolled the league throughout the 2023-24 campaign. Holiday, of course, never suited up for the Blazers.

This move will save the Celtics around $40 million in luxury tax penalties, as Holiday still had two years and $72 million left on his contract. At 35, and with Boston’s title hopes effectively shelved after Jayson Tatum’s Achilles tendon rupture, Holiday’s departure may not be the last.

Had they kept the roster intact, the Celtics were headed straight into the dreaded second apron – the NBA’s severe cap penalty zone for teams whose payroll far exceeds the set threshold. The team’s new ownership group, led by Bill Chilshom, acquired the franchise for $6.1 billion this past March and doesn’t seem keen to throw good money after bad on a roster with slim championship prospects. With Tatum sidelined for much of the coming season, the mood in Boston is turning toward a strategic retreat.

Kristaps Porzingis may be the next to leave, and even Jaylen Brown’s name has surfaced in early trade speculation – though that scenario appears much more complicated.

This past season, the veteran guard averaged 11.1 points, 4.3 rebounds, 3.9 assists, 1.1 steals and shot 35.3% from beyond the arc. While he remained a positive contributor, the dip from his debut season in Boston was noticeable. That year, he was named to the NBA’s All-Defensive Second Team and hit a blistering 42.9% from three, averaging 13.2 points and reaching the coveted 50-40-90 shooting thresholds.

On the other end of the trade, Anfernee Simons arrives in Boston as a 26-year-old shooting guard selected 24th overall by Portland in the 2018 draft. A gifted scorer, he’s averaged 20 points per game across the past four seasons, during which he’s become a key piece of the Blazers’ rotation. In that span, he’s launched 8.5 threes per game on average and converted 38.2% of them.

Given that Boston’s offense revolves heavily around perimeter shooting, Simons looks like a good fit for Joe Mazzulla’s system. More importantly for the front office, he’ll be a free agent next summer, giving the Celtics flexibility – they can either retain him or reallocate the $27 million he’s owed this season elsewhere.

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