Celtics trade proposal sends Jrue Holiday to West Coast for pair of All-Defensive players

The Boston Celtics have been one of the best teams over the past few years, but even they have some mistakes to recover from.

This offseason, the Celtics might be able to take some strides toward their next championship run with some big moves. While Jayson Tatum is still recovering from a torn Achilles and Jaylen Brown is seemingly off the table, Boston could make some shocking moves in the next few weeks.

One of those big moves could be to send Jrue Holiday out in a deal to help the team’s cap situation moving forward. One of the routes to getting Holiday to a new team could be to rectify a past mistake.

In a recent Bleacher Report article re-drafting every team’s worst pick in the past 10 years, Matt Velazquez suggested that Boston’s biggest mistake was taking Romeo Langford with the No. 14 pick in 2019 over Matisse Thybulle. While it is too late to make the right pick from that draft, it isn’t too late to get Thybulle into Boston.

With Holiday potentially on the way out, the Celtics could send their championship point guard to Portland for Thybulle, Robert Williams III and Duop Reath. For the Blazers, Holiday could add some veteran leadership and help them take the next step, potentially taking over for Anfernee Simons if he gets dealt this offseason.

Meanwhile, the Celtics can buy low on Thybulle, who played 15 games last season, and Williams, who has infamously had injury issues throughout his career. While it’s risky to buy into players with such notable injury histories, this move adds some depth and helps Boston’s financial situation. 

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And if the move doesn’t work out on the floor, the Celtics still gained some flexibility with Holiday’s contract off the books, and Thybulle and Williams are both on expiring deals.