Celtics Sending Jrue Holiday For Anfernee Simons and Picks Confuse Fans: “Why the Blazers Do This?”

Boston Celtics were facing a $500 million wage bill next season if they kept Jrue Holiday, Kristaps Porzingis and the rest.

Celtics Sending Jrue Holiday For Anfernee Simons and Picks Confuse Fans: “Why the Blazers Do This?”

Boston Celtics send Jrue Holiday to Portland Trail Blazers for Anfernee Simons (Image via FirstSportz)

When the Boston Celtics traded for Jrue Holiday and Kristaps Porzingis to pair with Jayson Tatum, Jaylen Brown, and Derrick White, the idea was to assemble a team that could win at least 2-3 NBA titles. In two seasons, that experiment netted one championship.

This season, their regular-season performance was not as good as last year’s, as many players battled injuries. Despite that, every other analyst believed the Celtics had everything going for them to defend their crown.

The way they won the 1st round of the 2025 playoffs, that notion received sufficient proof. Then they met the New York Knicks, and all hell broke loose. Last year’s champions lost both opening home games after building up 20-point leads.

Then Jayson Tatum suffered a season-ending injury to his Achilles tendon. That injury, though, was not the reason for the loss, and their fans understood that Tatum may not play with the same roster again next season.

The Boston Celtics have the league’s highest payroll, with an approximately $500 million bill next season. To avoid that, they would need to break the team apart, and the 1st option was to let go of the veteran stars.

Shams Charania reported that the Celtics negotiated a deal with the Portland Trail Blazers to send Jrue Holiday in exchange for young guard Anfernee Simons and two 2nd round picks. This helps the Massachusetts-based team relieve itself of Holiday’s $135 million contract.

They might be saving just $8.6 million in annual cap space, but in Anfernee Simons, they are getting a guard nine years younger than Holiday, who they can audition next season before handing him an extension. Simons is on an expiring contract.

Fans confused about Jrue Holiday for Anfernee Simons’ trade

When Shams Charania’s social media post triggered notifications sounds on phones, basketball fans were left confused. On one hand, they understand that Jrue Holiday is a terrific defender who helps teams build a championship mindset.

On the other hand, he is 35 years old and could start to fade away after a season. On top of that, the Portland Trail Blazers gave up a young piece they could build on, along with picks, to take on that colossal contract. These details left basketball fans shaking their heads and reacting accordingly on social media.

Jrue Holiday might be the missing piece for the up-and-coming Trail Blazers. They need a veteran star who can help elevate the squad. However, many believe this was a steep price for an aging star whom the Boston Celtics felt was no longer needed.

Anfernee Simons will have pressure trying to replace Jrue Holiday

For Jrue Holiday, this move might be a breath of fresh air. He will be moving to a city where the pressure from both fans and the media will be a lot less. The 35-year-old can help build the Portland Trail Blazers quietly and without distractions.

Anfernee Simons will have a lot of pressure in Boston
Anfernee Simons will have a lot of pressure in Boston (Image via Ball Report/X)

Considering he has time before he becomes a target for another trade or is released, the die-hard family man can relax and play basketball. It will not be the same for Anfernee Simons, who gets thrown into the Boston Celtics fire immediately.

Until Jayson Tatum returns, expect a lot of the scoring pressure to be on the IMG Academy graduate. He knows he has to perform if he is to earn his next big payday. If not, the Celtics can easily move on from him and find the next replacement.

The Florida native will also have the pressure to defend the way Holiday used to do. If either the franchise or their passionate fans find him to be lacking, they will waste no time letting him know loud and clear what they think of him.

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