Yardbarker
x
Grading Trail Blazers Landing Jrue Holiday for Afernee Simons
Apr 13, 2025; Portland, Oregon, USA; Portland Trail Blazers guard Anfernee Simons (1) and Portland Trail Blazers head coach Chauncey Billups share a moment before the Trail Blazers play Los Angeles Lakers at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images Jaime Valdez-Imagn Images

The Boston Celtics traded Jrue Holiday to the Portland Trail Blazers for guard Anfernee Simons and two second-round picks.

The trade comes out of nowhere for the Blazers, who were not linked to Holiday and there were several other more interested suitors for Simons, but this is the trade that the front office chose to go for.

The deal sees the Blazers move on from Simons, the team's former late first-round pick in the 2018 draft.

Given the team already had Shadon Sharpe and Scoot Henderson, Simons was the most likely guard on the roster, given that he is on an expiring deal.

Here is the grade for the massive trade:

Blazers: D

The Blazers are taking on Holiday's massive contract which has three seasons left on it and has him earning more than $30 million per season still.

The 34-year-old guard still plays at a high level, offering good defense and secondary ball-handling that complements any back-court running mate.

The main issue with the trade is that Holiday is past his best, and he is best optimized on a winning team, who can get the best out of Holiday and keep his minutes down.

The two-time All-Star has only played more than 80 regular-season games twice in his career. He is known for missing part of the season with an injury, and even when he does play, he carries some kind of lingering issue.

The Blazers are still a ways away from competing in the stacked Western Conference, and the Holiday trade doesn't provide enough to get them in a higher tier of contenders.

In the modern salary cap era, his contract will hurt the team's future flexibility and become a burden soon.

Many NBA experts predict that the Celtics will need to attach draft compensation to move on from Holiday, but the Blazers were the team that offered draft capital and a younger, cheaper player.

Holiday does offer the Blazers something, but it is hardly enough to justify the trade.

Oregon Has Issued Resolution to Keep Blazers in Portland Amid Sale

Report: Blazers Have Held Trade Conversations on Robert Williams With One Team

Blazers Must Take Advantage of Raptors Rumored Fire Sale

Blazers Draft Rumors: Portland Linked to Big Man Amid Trade Speculation

Blazers Make Big Coaching Announcement

Blazers Have Massive Jerami Grant Problem

East All-Star Being Linked to Blazers

For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.


This article first appeared on Portland Trail Blazers on SI and was syndicated with permission.

More must-reads:

Customize Your Newsletter

Yardbarker +

Get the latest news and rumors, customized to your favorite sports and teams. Emailed daily. Always free!