Celtics Reportedly on Jrue Holiday's List of Desired Destinations

Is it better to trade for Jrue Holiday now, or should the Celtics save their draft capital for the stars who may become available next summer?

Michael McLoone-USA TODAY Sports

The Portland Trail Blazers will work quickly to reroute Jrue Holiday in a deal designed to expedite their rebuild. There's a legitimate chance this move will happen ahead of media day on Monday.

As previously detailed by Inside The Celtics when exploring what it might cost Boston to acquire the two-time All-Star and whether the price is worth paying, Holiday is on a $36.8 million contract, carrying a $37.4 million player option for next season.

Interested teams may disregard his preferences, but the 33-year-old guard's ability to opt-out and enter free agency next summer gives him some leverage in where he ends up.

David Butler II-USA TODAY Sports

With contenders across the Association in pursuit of his services, the California native's wish list consists of the Celtics, Miami Heat, both Los Angeles-based teams, the Philadelphia 76ers, and Chicago Bulls, per the Miami Herald.

Perhaps Boston believes adding the five-time All-Defensive team selection is worth going over the second apron. Even if an extension gets reached after doing so, the organization can reshape its roster's core to limit how many years it crosses that threshold.

But the package the Celtics put together will either include Derrick White, Al Horford, or Robert Williams, or they'll get creative, utilizing a Blake Griffin sign-and-trade in a proposal centering on at least two and likely more first-round picks.

White, 29, is younger and has proven more effective defending Damian Lillard. Proceeding with two of Horford, Williams, and Kristaps Porzingis, especially the latter two, given the former's aging gracefully and their durability concerns, also puts Boston in a precarious position.

And regarding the draft capital involved in any package for Holiday, while Giannis Antetokounmpo seems likely to sign an extension with the Milwaukee Bucks next summer, stars like Luka Doncic and Joel Embiid could find new homes after the 2023-24 campaign.

Winslow Townson-USA TODAY Sports

Should the Celtics decide it's worth parting with Jaylen Brown to acquire a player such as the two mentioned above, they'll regret the restrictions a Holiday trade places on the draft picks they can offer.

But as the franchise quickly calibrates how best to move forward, perhaps pouncing now is the correct course of action.

Holiday won't match Marcus Smart's fiery demeanor; his shooting can prove streaky, though he did knock down 38.4 percent of his 6.1 three-point attempts last season, and he's better off the ball than on it. However, he'd replace much of what Boston had in its former floor general.

While the Celtics face steep competition for the 14-year veteran, if they can make this happen, especially without trading White, Horford, or Williams, they should prioritize their current championship chase and be okay with crossing the second apron this season and not worry about chasing stars who might become available later.

Further Reading

Celtics' Malcolm Brogdon Reportedly 'At the Center' of Clippers' Trade Talks

Bucks Acquiring Damian Lillard a Boost to One Celtics Rival, Potentially Fatal Blow to Another

Evaluating Whether Celtics Should Trade for Jrue Holiday

Jayson Tatum Preparing for Point-Guard Role This Season

Payton Pritchard, Eager to Help Celtics Seize Banner 18, Senses Teammates 'Urgency to Do Something Special'

Candace Parker on Celtics Trading Marcus Smart, Maximizing Tatum-Brown Tandem, Pat Summitt, and the Sports Matter Initiative

Brad Stevens Discusses Differences in Joe Mazzulla Entering Year 2 as Celtics' Head Coach

Here's What to Know About Celtics' 2023-24 Schedule

Examining How Celtics' Starting Lineup Might Shapeshift This Season

Dwyane Wade Discusses Jayson Tatum's Next Step, Him and Jaylen Brown's Challenge, Heat Culture, Pat Riley, Damian Lillard, and Life After Basketball

Why Celtics Should Enter 2023-24 Season Optimistic About Most Important Area of Improvement