It is time for the Boston Celtics to move on.
That was always going to be the painful reality of this summer, as the Celtics addressed an aging and supremely expensive starting lineup in the face of punitive restrictions in the league's collective bargaining agreement. Being light years above the second tax apron was going to prevent the Celtics from maintaining a contending team and cost the franchise's new owners a pretty penny. They were always going to be taking one or more contracts and dumping them into Boston Harbor like so many crates of tea.
The urgency for such a move has only skyrocketed in the wake of one of the worst weeks Boston has seen in a very long time, with franchise icon Jayson Tatum tearing his Achilles and expected to miss all of next season. A six-game loss to a New York Knicks team they were supposed to eviscerate has the Celtics knocked out and beat up, and with an uncertain future.
There are multiple options for Brad Stevens and company to consider, one of which is offloading some money, doing their best next year and trying to run it back two seasons from now when Tatum is healthy. The other end of the spectrum involves doing a complete reset around Jayson Tatum, trading all of their core pieces, and building a brand-new team to contend for the next five seasons after next year.
Whatever path this team takes, there should be one common denominator: trading Jrue Holiday.
The Celtics have to trade Jrue Holiday
That level of bold statement is usually built on some sort of immense dissatisfaction. That's not the case with Holiday, who is by all accounts a phenomenal person, teammate and leader. If the Celtics don't trade for Holiday they don't win last year's title. His combination of versatile defense, playmaking and scoring as a supporting actor are ideal for a title contender, and that is why he has joined two different franchises and propelled them to a championship.
Now for the unfortunate truth: Jrue Holiday will turn 35 next month. He would turn 37 during the NBA Finals if the Celtics kept him and tried to run it back in 2026-27. His offensive game has continued to spiral over the last few seasons, and he averaged just 11.1 points per game this season, his lowest since his rookie year.
Holiday wasn't able to ramp things up in the playoffs, either, scoring just 9.5 points per game even with teammates in-and-out of the lineup. He shot only 35.3 percent from deep, and opponents were all-too-happy to leave him open if it meant shutting off the water to Jaylen Brown, Tatum or Kristaps Porzingis. His usage rate and assist percentage also hit career-lows as he handled less and less of the ball.
In contrast to his declining offensive skillset, his contract goes up. Holiday still has three years remaining on the four-year, $135 million extension he signed. He will make an average of $34.8 million over the next three years. It will be nearly impossible for the Celtics to maintain a contending team paying that much money to a player with declining skills like Holiday.
His defense remains excellent, and he helps a team more than his box score suggests. He is not a complete albatross on his contract, but given the expense of the rest of the roster, Boston has to make a move.
Perhaps another team wants to roll the dice on Holiday being exactly what they need in a deal. If the Celtics can move him at neutral value in a deal that lowers their payroll, they should probably do that. If they can attach a nominal asset and clear most of his salary, they should pursue that even more strongly.
Gaining financial flexibility will enable them to make the next move to arm up for a championship; right now they are hamstrung by their salary situation and are facing a year of non-contention as their best player recovers from what could be a career-defining injury.
Jrue Holiday may still have fans around the league who are willing to eat his contract cost. If Boston can find them, they need to work out a trade -- not because Holiday has done anything to warrant shipping him out of town, but because it's the best move for the future.