The Celtics stayed on the sidelines as expected for the Damian Lillard trade derby but the fallout of the deal will be felt throughout the Eastern Conference. With Lillard finding a surprise new home in Milwaukee, the NBA’s attention now turns to the next obvious premier name on the market in Jrue Holiday.
The Blazers will be shopping the 33-year-old point guard in the coming days as they attempt to collect more assets while rebuilding around a younger backcourt already in place.
Several reports have linked the Celtics as likely bidders for the defensive-minded guard. However, multiple league sources told MassLive they do not expect Boston to come out on top in what is guaranteed to be a competitive bidding war among contenders in both conferences.
What exactly are the factors in play here for Boston? Let’s take a closer look at a few important elements to consider as negotiations play out.
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Holiday’s Contract
Holiday has two years left on his deal, earning just shy of $37 million for this coming season along with a player option for 2024-25 that’s widely expected to be declined by Holiday per league sources.
Holiday was looking for an extension in Milwaukee and will be unable to sign one with a new team for six months per CBA rules. However, the problem for the Celtics is they have already committed to a third big fish for the short term with Kristaps Porzingis, who was given a two-year extension back in July.
The Celtics are also set to hand out two super max contracts to Jayson Tatum and Jaylen Brown, the first of which kicks in next season with Brown. Boston’s payroll is already projected to be beyond the second apron with their current commitments for 2024-25 and that’s before factoring in what Holiday would command (likely $30+ million per year in his new deal). The Celtics may not have the payroll budget to pay that next big deal while keeping their current core intact and/or want to deal with the competitive disadvantages that result from going over the second apron. In that case, a deal for Holiday would potentially be a one-year rental, which could very well impact Boston’s offer.
Compensation
NBA trade rules would require the Celtics to send out at least $33.5 million in a trade for Holiday. That’s not an easy number to get to for the Celtics with their current payroll without messing with important parts of their core.
Malcolm Brogdon is an easy place to start as a potential trade chip with his $22.5 million contract. From there though, the only realistic path is also including one of Derrick White, Al Horford or Robert Williams in the deal to make the money work. While there’s no doubt that Holiday is an upgrade on Brogdon, the team is very high on White as evidenced by Joe Mazzulla already naming him the new starting point guard earlier this summer.
Boston’s front line also has injury and age question marks so moving out Horford or Williams in a deal for Holiday suddenly leaves that position mighty thin and vulnerable if the one remaining starter-level big or Porzingis gets hurt. Beyond that? It’s a host of minimum-level players left in Luke Kornet and Oshae Brissett. Making this type of trade may have been easier to swallow with more frontcourt depth but the team let a lot of that talent out the door due to money (Grant Williams) or to make separate trades work moneywise (Mike Muscala in Smart deal).
On top of that conundrum, there’s also the fact that the Blazers are going to be seeking out future draft compensation in any deal so they are going to want picks on top of players for Holiday. Brogdon and Williams/Horford are important role players for a contender but they will be of little use for Portland (except perhaps Rob Williams although his fit behind DeAndre Ayton would be tricky from a cost standpoint).
The Blazers would try to flip these players for more assets but the market for some (Brogdon) could be limited due to his position and salary. A straight up trade from Boston players for players is likely to be outbid by other competitors quite easily once picks are included. Bringing in Holiday would potentially open up other holes throughout the roster with limited means to fill them.
Final Thoughts
The Celtics are going to do their due diligence here, as they should when any player like Holiday becomes available. The team was in the running for him back in 2020 per a source when he last hit the trade block but were outbid by the Bucks. Three years later, it’s fair to wonder if he’s worth the lofty price tag for likely a one-year rental when it comes at the expense of multiple key role players and draft picks.
The Celtics still have the trade ammo to make a big swing this offseason but this is a pitch they likely will let go by.
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