Celtics make their first major trade of offseason

A cost-cutting summer for the Celtics officially kicked off late Monday night.

And it started with a name bandied about as a likely trade candidate, too, with guard Jrue Holiday traded from Boston to Portland. In exchange for Holiday, the Celtics will receive Anfernee Simons and two second-round picks.

ESPN's Shams Charania was the first to report the trade.

In what is a bit of a full circle moment of sorts considering that the Blazers sent Holiday to Boston after trading Damian Lillard to Milwaukee, Portland is the first team to capitalize on Boston's tax issues (and the Jayson Tatum injury) that's by all means put the C's into more of a 'retool' mode after back-to-back win-now years that included a title in 2024 and second-round exit in May.

A Celtic for two seasons, the 35-year-old Holiday averaged 11.1 points and 3.9 assists per game in 62 games this past season, and most notably saw his success from deep drop, going from a 42.9 percent mark from three-point range in 2023-24 down to 35.3 percent this past season.

And though his Boston tenure was a short one, it was memorable, as Holiday will be remembered for his game-winning steal on the Pacers' Andrew Nembhard in the closing moments in Game 3 of the 2024 Eastern Conference Finals. That steal helped earn the Celtics a 3-0 series lead versus the always-dangerous 2-1 series would-have-been, with the Celtics successfully closing out the Pacers in a four-game sweep on the way to a title.

Holiday, who is one of just three players to win multiple titles during the 2020s, has two years remaining on his current contract, and at over $32 million in 2025-26 and over $34 million in 2026-27. Holiday is also in possession of a player option (at over $37 million) as a 37-year-old in 2027, too.

Simons, meanwhile, comes to the C's after averaging 19.3 points and 4.8 assists, along with a 42.6 field goal percentage (36.3 percent from deep), in a career-high 70 games for Portland during the 2024-25 season.

The 6-foot-3 Simons, who was a first-round pick in 2018, certainly fills a need as a bonafide scoring option for a Tatum-less Celtics club, having 23 games of at least 25 points for the Blazers this past season.

Simons is also on an expiring contract, making him a potential trade chip for the Celtics if this is indeed the retooling year it may look like for the club.

With the trade, the Celtics are $18 million away from getting below the second apron, meaning that more moves are indeed coming for the Celtics.