The idea of the Celtics trading Holiday picked up steam after they were eliminated by the New York Knicks in the second round. Jay King of The Athletic reported after that series that "several contending teams" were interested in the UCLA product should Boston decide to shop him.

The Celtics made their first big deal of the offseason on Monday night, trading away Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks. The two second-round picks are a 2030 Knicks selection and a 2031 Blazers pick, a source tells MassLive. ESPN was first to report the Holiday trade.

The Boston Celtics have reportedly traded Jrue Holiday to the Portland Trailblazers, according to ESPN. In return, the Celtics are receiving Anfernee Simons and two second-round draft picks.