<p>Shams Charania has once again broken a trade in the NBA! The Boston Celtics have traded their veteran point guard Jrue Holiday to the Portland Trail Blazers for a young guard. Let&#8217;s talk hoops!</p>
<p><em>Check out <a href="https://affiliates.bettingnews.com/register/betonline/" target="_blank" rel="noopener">BetOnline</a> for how this changes <a href="https://affiliates.bettingnews.com/register/betonline/" target="_blank" rel="noopener">next year&#8217;s champion and playoff team odds!</a></em></p>
<div id="attachment_76375" style="width: 1010px" class="wp-caption alignnone"><img loading="lazy" decoding="async" aria-describedby="caption-attachment-76375" class="wp-image-76375 size-full" src="https://wp.bettingnews.com/wp-content/uploads/2025/06/3.jpg" alt="Jrue Holiday looking mildly upset in a green Celtics jersey." width="1000" height="510" srcset="https://wp.bettingnews.com/wp-content/uploads/2025/06/3.jpg 1000w, https://wp.bettingnews.com/wp-content/uploads/2025/06/3-300x153.jpg 300w" sizes="auto, (max-width: 1000px) 100vw, 1000px" /><p id="caption-attachment-76375" class="wp-caption-text"><em>The Celtics are moving on from a player that was once considered their final piece. Life moves fast.</em></p></div>
<h2>Jrue Holiday traded for Anfernee Simons</h2>
<p>The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. This is a great trade for both franchises as Jrue Holiday brings a veteran presence to an already pesky Portland team that almost slipped into the Play-In Tournament this year.</p>
<p>Holiday was drafted No. 17 overall in 2009 to Philadelphia. The 35-year-old has career averages of 15.8 points, 6.2 assists, and 1.4 steals per game. He is a two-time champion with the Milwaukee Bucks and last year&#8217;s Celtics. He&#8217;s coming off a year where he played 62 games, but averaged his lowest scoring total since his rookie campaign. The Celtics face next season without superstar Jayson Tatum. This is a welcome trade that lets fans know front office and ownership still thinks they can compete next season.</p>
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<h3>Boston&#8217;s Money Troubles</h3>
<p>Furthermore, Simons is young so he can fit into their long-term plans or be a one-year rental. This is a good trade. The move also saves the Celtics a projected $40 million in tax savings for 2025-2026. Massive savings. The cherry on top? Simons is extension eligible already. Unfortunately, Boston will still be $18 million over the dreaded second apron. They do not have a lot of maneuverability because of that so having the flexibility of Simons deal is very welcome.</p>
<p>Simons was the No. 24 overall pick out of IMG Academy in 2018. He learned under Damian Lillard and is a excellent shooter. Anfernee holds a career average of 38.1% on serious volume especially the last three years. He is the kind of player that will fit right in Mazzulla&#8217;s offense. Jrue Holiday was starting to show his age, but now he can enter into a new role with Portland.</p>
<p>Additionally, surrendering just two second-round picks is great. Portland gets their veteran. Jrue Holiday can teach Scoot Henderson a lot about being a long-term pro and defensive skills. Boston stays in contention by adding a 20-point scorer. A rare but conclusive win-win here.</p>
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<h3>Shoutout Brad Stevens!</h3>
<p>Here is a quick oversimplification of some of the moves last year&#8217;s Executive of the Year for the Celtics made:</p>
<ul>
<li>Moved Kemba Walker for Al Horford</li>
<li>Traded a pair of players and a first-round pick for Derrick White</li>
<li>Swapped Marcus Smart for Kristaps Porzingis</li>
<li>Acquired Jrue Holiday and <strong>won the championship</strong></li>
<li>Acquired Anfernee Simons for an aging veteran</li>
<li>Extended all his core pieces</li>
</ul>
<p><strong>This story will be updated as additional information is made available. </strong></p>
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<h2>Thanks for Reading!</h2>
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