Brian Robb: Celtics savvy bet on Jrue Holiday trade eliminates key predicament

Boston Celtics president of basketball operations Brad Stevens speaks at a news conference during the NBA basketball team’s media day, Monday, Oct. 2, 2023, in Boston.

The Celtics’ sense of urgency to win a title now kicked up a notch this summer in the wake of betting big on a Kristaps Porzingis trade and extension back in July. That move also diminished the team’s margin for error when it came to depth across the roter with Marcus Smart and Grant Williams heading out the door in separate trades to make room for the big man’s salary.

When Jrue Holiday became available in the wake of the Damian Lillard trade to the Bucks in late September, Brad Stevens and the Celtics front office had to map out the potential risks and rewards of a pursuit in short order. Bringing aboard Holiday on an expiring deal would be an expensive option in terms of player and draft capital while also potentially hurting Boston’s depth in the frontcourt.

Ultimately, the team pulled the trigger on the move despite those caveats for the upgrades Holiday brings. Whether the team will be able to retain Holiday on a long-term deal remains to be seen (they can’t negotiate until 6 months after the deal was completed), but pulling off a major trade preemptively in October has to be seen as a success already in the wake of this week’s injury developments with Robert Williams in Portland.

Williams is expected to undergo major surgery on his right knee after suffering an injury on Sunday night per multiple reports. The likelihood now is he will miss several months, if not the entire season.

If the Celtics stood pat on the Holiday front back in September and watched the point guard go to another contender (Clippers?), Boston would be left in a miserable situation right now in the wake of Williams’ injury. One key trade and rotation asset would have vanished for the short term with his injury. Meanwhile, Malcolm Brogdon would still have been unhappy with the team in all likelihood in the wake of an early attempted trade to the Clippers back in June. For a team set on contending now, finding any meaningful in-season upgrades would have been daunting without emptying the team’s draft asset stash.

Instead, Boston’s front office was seemingly realistic about the possibility of this type of scenario unfolding with Williams given his tough injury history. Factoring that scenario into the calculus of the Holiday trade compensation was a smart gamble since the risk of standing pat entering the season was very real as well with that duo. There were certainly other players Boston would have gone after during the year if they came up short in the Holiday pursuit but there was no guarantee a player as accomplished as him would become available over the course of the year at an affordable price point.

To that point, the Celtics had no guarantee their remaining pool of player assets they would be willing to trade would stay healthy as well if they chose to wait. There’s something to be said for having an entire team’s core together from the start of the year as well, a goal that Boston was able to achieve with the Holiday deal as well.

In the aftermath of the blockbuster swap, the Celtics still have plenty of options for minor tweaks with Grant Williams’ TPE and smaller salary deals across the bench that could be moved for the right addition. Patience will be key now on that front as Stevens weighs the biggest needs going forward.

In the meantime, the Celtics brass can breathe a sigh of relief for getting out in front of an unfortunate injury situation with Williams. It’s tough not to feel for the former beloved Celtic, who luckily for him is on a long-term deal for another two years. Whether he will be able to command another big contract in the wake of his ugly injury history remains to be seen.

In the meantime, the Celtics’ bet to use Williams to help fill Marcus Smart’s void with Holiday already looks like a savvy move.