The confetti’s still being swept off the hardwood after the Oklahoma City Thunder claimed the 2025 NBA title, but NBA front offices aren’t wasting any time. Just as the offseason buzz began building, the Boston Celtics made the first jaw-dropping move, shipping out Jrue Holiday to the Portland Trail Blazers.
In return, they receive Anfernee Simons and a couple of second-rounders. It didn’t take long for NBA fans to light up social media with their unfiltered takes, and most aren’t holding back.
NBA Fans Baffled at the Celtics Trading Jrue Holiday to Blazers for Anfernee Simons
The trade caught fans completely off guard, as it was reported by ESPN’s Shams Charania.
While trades are a normal part of the NBA offseason, this one hit differently, especially considering Simons’ recent impact. His offensive versatility, particularly as a strong three-point shooter (Simons has averaged nearly nine 3-point attempts per game over his past three seasons), is unprecedented, which is why, for many fans, the deal simply didn’t make sense.
“WHY WOULD THE BLAZERS DO THIS,” one user wrote, clearly baffled by Portland’s decision to part ways with Simons and give up draft capital.
WHY WOULD THE BLAZERS DO THIS
— Jake (@playoffjake) June 24, 2025
Meanwhile, Holiday, a versatile, two-way guard known for his elite defense, calm playmaking, and high basketball IQ, is the kind of player you don’t usually let go. But Boston fans were already celebrating. “CELTICS WIN BY A LANDSLIDE,” another posted, echoing what a large chunk of NBA Twitter seems to believe: Boston may have just fleeced the Blazers.
Given Simons’ age and offensive upside, it’s easy to see why some view this as a huge W for the Celtics. Simons posted 19.3 points on a 42.6% FG per game in the 2024-25 season.
CELTICS WIN BY A LANDSLIDE
— Jason Petrucci (@Jpet_7) June 24, 2025
That said, not everyone is convinced this move is purely about basketball. “This was definitely a money move,” one fan commented, suggesting Portland might be motivated by long-term cap strategy rather than on-court results.
Holiday, the 2024-25 NBA Social Justice Champion, signed a four-year, $134.4 million contract with the Celtics. He is owed nearly $72 million in the 2026-27 and 2027-28 seasons. The trade saves Boston $40 million in luxury tax next season. On the other hand, Simons is joining Boston on an expiring contract, as ESPN’s Bobby Marks reported.
This was definitely a money move
— ChoZen (@ChoZenKun) June 24, 2025
There’s also the full-circle element: Holiday was originally acquired by the Portland Trailblazers in the Damian Lillard trade in 2023, only to be rerouted to Boston for two first-round picks. Now, he’s back with the Blazers, but this time, the cost was Simons and two second-round picks, not a haul of first-round picks.
MORE: Try Our Free NBA Mock Draft Simulator
Still, not all fans are pessimistic. One user flipped the script entirely, posting: “Portland going to the play-in now… this is incredible move for them.” That optimism is based on Holiday’s ability to stabilize a young roster and bring a winning mentality — something Portland’s lacked in recent seasons.
Portland going to the play in now… this is incredible move for them
— Ethan Price (@Paradox_EP) June 24, 2025
As one user simply put it: “Insane trade.” And really, that’s the best way to describe it. The Finals may be over, but if this deal is any indication, the 2025 offseason is going to be absolutely wild, as Charania had already predicted previously.
Insane trade
— Andrew (@andr3w) June 24, 2025
The trade can strengthen the Celtics’ roster as well. Simons gives the Celtics an added scoring punch and playmaking depth, which is especially valuable as Jayson Tatum recovers from an Achilles injury. The trade also helps Boston create flexibility under the salary cap.
With Simons heading to Boston on an expiring contract and Holiday making a surprise return to Rip City, all eyes will now be on what both franchises do next.
