FWIW, Hollinger's latest from The Athletic:
https://theathletic.com/4908778/2023/09/28/hollinger-damian-lillard-jrue-holiday/
Here's the section on the C's and Holiday:
3. To Boston for a pupu platter: The Celtics can get to a salary match on Holiday, but it’s complicated. Malcolm Brogdon would be involved, but he makes $22 million in 2025-26 and that’s $22 million more than the Blazers want to take back. Additionally, the second contract in a Boston deal has to be either Robert Williams or Al Horford, which nukes the Celtics’ frontcourt depth … unless they make the salary match Brogdon, Payton Pritchard, Luke Kornet, Sam Hauser, Jordan Walsh and a signed-and-traded Blake Griffininstead. A six-for-one. Whew.
Unlike a lot of contenders, the Celtics still have all their future picks to trade, plus they turned Marcus Smart into a future first from Golden State that is now available to put in a deal like this. Boston could offer five firsts if it wanted: 2024, ’26, ’28 (lesser of their own or San Antonio’s), and ’30, plus the Warriors’ top-4 protected pick this year.
The problem for Portland is Boston is good and should be for many years with Jayson Tatum and Jaylen Brown still in their mid-20s. The picks the Blazers would get would almost certainly be in the 20s. Ditto for that Warriors pick, too. It almost doesn’t matter the quantity, because what are the odds of getting a lottery-level pick quality out of this? I’d much rather own fewer end-of-decade picks from, say, the Clippers.
Between that and the fact that extending Holiday would make the Celtics shockingly expensive in two years, I’m a little less bullish on this one. But if Boston could pull this off while keeping Williams and Horford out of the trade, oh my goodness this defense. Nobody would ever score on them. And in terms of the sheer quantity of draft picks, this is the way for Portland to get the most.
Jrue Holiday is 33 this year, I'd be OK not extending him. Get two years out of him and then use the cap space on someone else while the Js are still at their peak.