Can something be both expected and shocking? If so, the trade between the Boston Celtics and the Portland Trail Blazers might count as such.
After two seasons in Boston, Jrue Holiday was dealt back to the Blazers — the team that first routed him to the Celtics in 2023 after the Damian Lillard trade — for Anfernee Simons and two second-round picks.
Let’s grade the trade:
Celtics: A
A trade of Holiday isn’t unexpected due to the Celtics losing Jayson Tatum presumably for all of next season with a torn Achilles. The Celtics are expensive, and they’re looking to shed both short- and long-term salary.
What’s shocking is their trade partner, and the return itself.
The Celtics managed, somehow, to extract assets out of the Holiday contract, which was extended last season to a number of $135 million over four years, leaving three years remaining on the deal.
That’s surprising for a few reasons, chief among them the fact that everyone knew the situation Boston found themselves in, and the Blazers not using that to their own benefit.
Simons gives Boston a floor-spacer who’s on team-friendly deal ($27.6 million, expiring), and who likely could sign a new deal worth less than his current compensation level.
He’s not a two-way dynamo who’ll defend multiple positions, as the Celtics have had a tradition of acquiring, but he’s a scorer, and a good one at that.
Simons has averaged 19.9 points over the past four seasons, and drained 3.2 3-pointers per night over that same time span. That part of his game will fit seamlessly into head coach Joe Mazzulla’s scheme, which saw the Celtics launch a league-leading 48.2 3s per game this season.
Ultimately, Boston got what it wanted by shedding salary, and even extracted assets, which has to be considered a win.
Blazers: C
Holiday is 35, and the Celtics were obviously in need of shedding significant money. For the Blazers to not only offer them a lifeline in the form of Simons, who is an expiring contract, but also two second-round picks, seems unnecessarily aggressive.
One reason for Portland’s aggressiveness could be that Holiday had stronger trade value around the league than assumed, but for a player who’s entering their 17th season, it’d be interesting to know what the Blazers were actually negotiating against.
Setting aside the trade package, Portland must surely feel as though Holiday levels them up, collectively, to a point where he’s worth the added money.
His defense and leadership qualities do remain rock solid, and he’ll make for a highly intriguing teacher to Scoot Henderson.
In totality, while you can see the vision of Portland if you squint, it remains odd that the Blazers went this hard after a 35-year-old with over $104 million left on his deal, knowing how much the Celtics needed to shed salary.
