Anfernee Simons Heads to Boston in Blockbuster Trade for Jrue Holiday
Wow, what a shake-up in the NBA — the Boston Celtics have officially traded Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round draft picks. This deal is both logical and surprising at the same time. Logical, because the Celtics were always likely to make a move after Jayson Tatum's devastating Achilles injury, and surprising, because they managed to get solid value back despite their urgent need to shed salary.
Let’s talk about what Boston gets in Anfernee Simons. Simons isn’t just a decent replacement — he’s a legit scoring threat. Over the last four seasons, he’s averaged nearly 20 points per game and has been one of the most reliable deep threats in the league, knocking down over three 3-pointers a night. That kind of offensive punch fits like a glove in Joe Mazzulla’s system, which is built around high-volume three-point shooting. With Tatum out, Boston needed someone who could keep the scoreboard moving, and Simons brings exactly that.
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Now, Simons isn’t known for defense, and he’s not going to replace Holiday’s all-world defensive impact. But what he lacks on that end, he more than makes up for in offensive efficiency and cap flexibility. He’s on a team-friendly contract worth $27.6 million that expires after this season. That’s a big deal for the Celtics, who were facing heavy luxury tax penalties and needed to get under the second-apron threshold. Essentially, this trade helps Boston stay competitive while also managing their finances — that’s a tough balance to strike, and they did it.
On the flip side, the Trail Blazers' decision is puzzling. They’re sending away a 26-year-old in Simons and two second-round picks for a 35-year-old Jrue Holiday, who is owed over $100 million for the next three seasons. Yes, Holiday brings veteran leadership and elite defense. Yes, he could be a great mentor for Scoot Henderson. But was it worth that much? Portland’s roster is young and rebuilding, and committing that kind of money to a veteran seems like an odd fit unless they believe they can flip Holiday again in the near future.
Holiday has missed 63 games over the past four seasons, including 20 last year. His game is still solid, but age and durability are real concerns. Maybe Portland sees this as a short-term boost and long-term asset play. But from the outside looking in, it feels like they gave up too much for too little certainty.
In the end, Boston gets a B+ to A grade here — they made a smart move to stay flexible without taking a huge step back. For Portland, it’s more of a C. The move has potential upside, but the price they paid feels steep unless Holiday returns to All-Defensive form and stays healthy.
The NBA never sleeps, and this trade just proves that front offices are always thinking two or three steps ahead — even when the moves don’t always make sense right away.
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