Evaluating Whether Celtics Should Trade for Jrue Holiday

Adding Jrue Holiday to replace Marcus Smart would bolster the Celtics' defense and give them a true floor general.

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The Milwaukee Bucks have pulled off a blockbuster move, acquiring seven-time All-NBA guard Damian Lillard in a three-team trade involving the Portland Trail Blazers and Phoenix Suns.

The seven-time All-Star joins forces with Giannis Antetokounmpo, Khris Middleton, and Brook Lopez, giving Milwaukee a quartet that makes them as formidable as any team in the NBA, including the Boston Celtics.

That's not to say the latter, who a recent ESPN survey polling 15 executives, scouts, and coaches across the NBA deemed the favorites to capture the Larry O'Brien Trophy this season, won't prove they're superior and live up to that billing. However, doing so just became more challenging.

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At a minimum, the move calms concerns about Antetokounmpo potentially leaving the Bucks for a new NBA home as early as next summer.

Another layer to this deal is the Portland Trail Blazers' intention to trade Jrue Holiday for more assets.

That begs the question of whether Boston should act quickly to acquire the five-time All-Defensive team selection.

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Teams across the league will perform their due diligence and check in with Portland about what it costs to land the two-time All-Star. That includes the Miami Heat, who mostly sat back this offseason, hoping Milwaukee would eventually settle on sending Lillard to South Beach.

But one of the reasons why that didn't happen was the Trail Blazers' lack of interest in acquiring Tyler Herro. Miami can still offer a package of picks and a promising young player like Nikola Jovic or Jaime Jaquez Jr.

For the Celtics, adding Holiday to replace Marcus Smart would bolster their defense, give them a true floor general, and help replace some of the grit they lost this offseason with the departures of Smart and Grant Williams.

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However, with the 33-year-old guard on a $36.8 million contract, carrying a $37.4 million player option for next season, and potentially seeking an extension upon getting traded, the salary-matching aspect of the equation alone will make it difficult for Boston to be his next destination, either.

Such a deal could cost the C's two first-round picks, Malcolm Brogdon, Al Horford, and Payton Pritchard. An alternative option is trading Robert Williams, making it easier to exclude Pritchard or at least only have to part with one first-round selection.

They could also offer a package of a first-round pick, Brogdon and Derrick White. Portland would then likely flip the latter two for more assets.

White is extension-eligible from the end of September until the regular season starts, a possibility he shared his opinions on earlier this summer.

If the Celtics are to swing a deal for Holiday, it's practical they'd prefer to part with the former Colorado Buffalo rather than sacrificing from their frontcourt.

Any deal for the 14-year veteran will also require them to get back to the minimum of having 14 players on their roster by opening night, a task that figures to take the franchise over the second apron if White's not in the trade.

It's business, and everyone in it understands that. But if Boston's willing to offer White in its proposal to land Holiday, if the latter goes elsewhere, it could leave the Celtics needing to mend fences with two of its guards.

It's another factor to assess as they determine how much they're willing to disrupt what's in place in this pursuit.

Further Reading

Thoughts on ESPN's NBA Survey's Celtics' Assessment

Here's What Jayson Tatum Told Celtics After Ime Udoka's Removal

Details of Why Malcolm Brogdon's Upset with Celtics Revealed

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

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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