The Boston Celtics seem to believe that if they keep smashing buttons, a championship will eventually materialize. The Celtics have reconfigured around Jaylen Brown and Jayson Tatum countless times. The early Tatum-Brown years saw them trying to build a contender through the Joe Lacob two-track plan that nearly destroyed Golden State.
After Gordon Hayward fractured his tibia and ankle in the opening minutes of the 2017 season, followed by Kyrie Irving departing for Brooklyn in the summer of 2019, Tatum and Brown were recast as the main characters in a rebooted Boston ensemble. Danny Ainge took a crack at accelerating Tatum and Brown’s ascension, but that was fruitless. Brad Stevens’ promotion upstairs, Ime Udoka holding stars accountable and the return of Al Horford culminated in a trip to the Finals.
However, Udoka’s illicit relationship with a member of the Celtics organization forced the organization to scramble its coaching staff on the fly. Damon Stoudemire decamping for Georgia Tech during the season robbed Joe Mazzula’s staff of a veteran coach to guide his steep learning curve at the helm. Ultimately, it was losing in the Conference Finals to an 8-seed rung the alarms, spurring Boston’s front office to make drastic roster changes this summer.
In July, Boston jettisoned its heart and soul, Marcus Smart, as part of a three-team deal with Memphis and Washington for Kristaps Porzingis. It was unfathomable before the offseason began that Smart would be dealt unless he was part of a package deal for a bonafide superstar. Porzingis would have been an intriguing fit alongside Robert Williams, and would have likely allowed Horford to play a more diminished role after averaging 30 minutes a night at the age of 37.
Instead, on the eve of training camp, Boston jettisoned Williams, the disgruntled Malcolm Brogdon, and two future first-round picks including the Warriors’ 2024 top-four-protected pick, and their own 2029 unprotected first to the Blazers for the 33-year-old Holiday
Shedding Williams on top of the Smart trade doubles the riskiness. His emergence during the 2021-22 season that ended in a Finals loss to Golden State warped Boston’s defense into the NBA’s best. Williams’ return to the Celtics starting lineup is what ignited their recovery from a 3-0 Eastern Conference FInals series deficit. In adding Holiday, the Blazers essentially single handedly escalated the Eastern Conference cold war by putting Lillard on a contender and simultaneously arming one of their chief rivals with the Lillard stopper. That’s not hyperbole either. Holiday (and Rajon Rondo) handcuffed Lillard and CJ McCollum to the stanchion in a 2018 first round upset of the Trail Blazers. As evidenced by his on-court chemistry with Rondo, Holiday’s versatility will allow him to thrive in lineups alongside Derrick White.
However, Holiday came at a price. Williams was one of the leading vote-getters for Defensive Player of the Year the last time he was healthy for more than half the season and a intimidating shot swatter whose bite in the paint made Boston’s defense purr. By acquiring a pair of expensive bookends to their lineup in the final years of the deal, team president Brad Stevens has narrowed their focus on the here and now.. Holiday and Porzingis are potentially in the final years of their respective deals. Porzingis exercised his player option before the season to facilitate the trade to Boston and Holiday has an option for 2024-25.
How this patchwork roster will gel on the floor is one of the season’s unknown mysteries. Presumably, they shouldn’t skip a step defensively. Offensively, Holiday is a more natural playmaker than Smart without dropping off defensively. Smart is still the only guard to win the ultimate defensive prize in nearly 30 years, but Holiday has been a model of consistent excellence being named to five All-Defensive teams. Boston was not content to stay the course.
At the very least you can never accuse Boston of being complacent. Rather than resting on their laurels, Boston tinkered and tinkered. It’s not the home run Jaylen Brown for Donovan Mitchell trade that was dreamt about, but the Celtics have to at least give this unit a chance. Besides, Brown is ineligible to be traded until next summer after signing the richest extension in league history.
Boston is running out of assets to offload for talent. For now, Brown is safe, but if the 2023 season goes sour, that job security may dissipate. The message being sent by Boston to everyone except for Tatum is that nobody is safe.
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