Boston Sports Tonight

Can Celtics land Jrue Holiday? Mannix details ‘steep' asking price

Is there a realistic path for the Celtics to acquire the talented two-way guard?

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There's another shoe to drop after the Milwaukee Bucks' surprising acquisition of Damian Lillard. Might that shoe land in Boston?

The Bucks' three-team trade with the Trail Blazers and Phoenix Suns to add Lillard sent veteran guard Jrue Holiday to Portland, which reportedly plans to immediately trade Holiday after drafting its point guard of the future, Scoot Henderson, with the No. 3 overall pick.

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Several teams are expected to have interest in Holiday, a two-time All-Star and three-time All-Defensive First Team selection who played a key role in Milwaukee's 2021 championship. And the Celtics reportedly are among them.

But what might it cost to acquire Holiday in a trade with Portland? Sports Illustrated's Chris Mannix shared what he's hearing Wednesday on NBC Sports Boston's Boston Sports Tonight.

"The asking price is going to be steep because there is going to be a bidding war for Jrue Holiday," Mannix said, noting that the Los Angeles Clippers, Philadelphia 76ers, Miami Heat all likely will pursue Holiday.

"My early read of the landscape is that it's probably going to cost two first-round picks to get Jrue Holiday. It's going to at least cost one first-rounder and potentially a blue-chip type prospect that fits into the rebuild in Portland.

"I think the Celtics should go after him. I think they should be really aggressive. But I also think they should be prepared for a very steep asking price."

Holiday would be a great fit in Boston. His defensive prowess would offset the loss of 2022 Defensive Player of the Year Marcus Smart, and he'd be an upgrade from Smart offensively after averaging 19.3 points and 7.4 assists per game last season while shooting 38.4 percent from 3-point range.

Holiday also has a pair of Boston connections: He was teammates with Celtics star Jayson Tatum on the USA Basketball squad that won gold at the 2020 Summer Olympics, and his former assistant coach in Milwaukee, Charles Lee, joined the C's staff this offseason.

The 33-year-old carries a $36.8 million cap hit for the 2023-24 season, however, and has a player option worth $39.4 million in 2024-25 that he could decline to hit free agency next summer. So in order to absorb Holiday's salary on a one-year rental, the Celtics most likely would need to send Malcolm Brogdon ($22.5 million cap hit) and Robert Williams ($11.5 million cap hit) to Portland.

Based on Mannix's intel, Boston may need to add a first-round pick to that proposal, and/or another depth piece to make up the roughly $2.8 million gap between Holiday and the combined salaries of Brogdon and Williams.

Should president of basketball operations Brad Stevens give up Brogdon, Williams and a first-round pick to land Holiday? There are arguments for both sides: Williams is an extremely valuable defender and dynamic rim-runner when healthy, and dealing him would leave Boston thin in the frontcourt with an injury-prone Kristaps Porzingis and an aging Al Horford. Then again, Williams comes with his own injury concerns, and a "Core Four" of Tatum, Jaylen Brown, Kristaps Porzingis and Holiday would be championship-caliber.

At the very least, expect Stevens to give Blazers general manager Joe Cronin a call to explore a possible Holiday deal as Portland weighs its options.

Brian Scalabrine joins Trenni Casey on Arbella Early Edition to discuss how the Celtics stack up in the East after the Bucks acquired Damian Lillard in a blockbuster deal. Scal also weighs in on whether the C's should pursue Jrue Holiday
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