The Damian Lillard trade sweepstakes are over, and now, his old team is getting right back to making calls about trading a guard. The biggest name that the Portland Trail Blazers received in the deal that sent Lillard to the Milwaukee Bucks was Jrue Holiday, the standout two-way guard who was crucial in getting Milwaukee over the hump in their pursuit of a championship.
If Portland wanted, it could keep Holiday around for a bit, let him serve as a mentor for their bevy of young guards, and look to move him at the trade deadline to a team that wants to make an all-in move during the season. But according to Shams Charania of The Athletic, it seems far more likely that they move quickly.
“The Bucks sent two-time All-Star Jrue Holiday to Portland to acquire Lillard, and I expect the Blazers to be active in the next few days to find a new landing spot for the veteran guard,” Charania reported on Friday morning.
It begs the question: Which teams could use Holiday’s services the most? Holiday’s one of the best all-around guards in the league, a snug fit on basically any roster, and one of the NBA’s most highly-respected guys, which is to say that the Blazers are in a pretty good spot here. There will be a bidding war to acquire his services, even though he is slated to become an unrestricted free agent at the end of this season if he declines to pick up his player option for 2024-25. With camp starting soon, teams interested in acquiring Holiday should be incentivized to move quickly to get in him before the season begins, which would theoretically drive up the bidding even more.
There are a ton of teams that could end up looking into a Holiday deal. Here, we’re going to look at the ones that make the most sense, both in terms of wanting to compete right now and having the stuff to make a deal happen.
6. Boston Celtics
Does Boston desperately need Holiday? Not really, no — they have Derrick White as their presumed starting point guard and felt confident enough in his ability to run the show that the team traded away Marcus Smart. Having said that: Boy, can you imagine this Celtics team with Jrue Holiday on it? Holiday has pushed one Eastern Conference contender with title aspirations over the hump before, and it’s not hard to see how he could do the same thing here if he ended up on this team.
Boston has a ton of picks it can potentially trade, including a top-4 protected 2024 selection from the Warriors, and a reportedly disgruntled guard in Malcolm Brogdon who could head the other way. Figuring out how to make the rest of this work financially would be tricky — would Boston even consider this if they’d have to move one of Robert Williams or Al Horford? — but there would not be a better starting five in the NBA than Holiday, Jaylen Brown, Jayson Tatum, and any two of Horford, Williams, and Kristaps Porzingis. That, mixed with how he can initiate the offense and let Brown and Tatum focus on other things, makes the thought of him in Boston awfully fun.
5. New York Knicks
New York is sitting and waiting to strike when an All-NBA player hits the trade market. Why not make a move that: 1. Doesn’t really compromise their ability to do that and, 2. Gets them a guy who fits really well alongside Jalen Brunson in their backcourt? The Knicks have a boatload of future first-round picks, including four in the 2024 NBA Draft (their own and protected selections from Dallas, Detroit, and Washington). They can’t make all of these picks, and they have to do something at some point. Would two of those picks, one of their own future picks, Evan Fournier’s salary, and a young player work? Would they want to move R.J. Barrett? Would the Blazers want Immanuel Quickley (along with whatever else New York would need to add to make this work financially)? I’m assuming Quentin Grimes, who the team had zero interest in moving during its pursuit of Donovan Mitchell, would be off the table, but who knows?
Tom Thibodeau loves defense and toughness, both of which Holiday brings in droves. He’d be part of a very good backcourt with Brunson, would give him and Julius Randle room to cook, and if they could sign him to an extension, he’d be an excellent player alongside whomever the Knicks acquire when that day comes for their really big swing.
4. Golden State Warriors
Just think for one moment about a Steph Curry-Jrue Holiday backcourt. They have a big ol salary to make things work out financially in Chris Paul, they could sweeten the pot with some combination of picks (say, their 2026 and 2028 firsts) and young players (Jonathan Kuminga and/or Moses Moody would be sensational fits on a young Blazers team), and they’d probably care less than anyone else on this list about Holiday potentially being a one-year rental. The “who comes off the bench?” question that exists right now with Paul in town would become more of a conversation, and it’s worth wondering if the Gary Payton II trade saga from last year soured relations between the teams. But if that’s not a hang up, Golden State should 100 percent kick the tires on a trade here — all that matters is to win as much as possible before Curry’s career comes to an end, and this would get them closer to accomplishing that goal.
3. Los Angeles Clippers
Considering their links to James Harden this offseason, the Clippers sure seem like a team that could use some backcourt help, even though Terance Mann is perpetually underrated, Bones Hyland is a promising youngster, and Russell Westbrook is back on a new deal. Holiday, a Los Angeles native, would give Ty Lue the sort of versatile perimeter defender that he loves, all while giving them a steady hand on offense when Kawhi Leonard or Paul George needs a break (or, in a worst-case scenario, miss time due to injuries). It also stands to reason that Steve Ballmer would have no qualms about signing him to a contract extension — presumably one that puts him on a similar timeline to Leonard and George, who are also potential free agents next summer — ahead of the team moving into their new arena next season.
They have the sorts of big expiring contracts that can work as salary ballast here, although players like Marcus Morris and Robert Covington may be helpful for them this season. Two big questions: Would the Clippers want to move a young player like Mann or Hyland if the Blazers demanded it? Would they really want to dip into their stash of picks that is just now getting replenished following the monster deal that landed them George (and, by extension, Leonard)? If the answers to both are yes, that would be one hell of a trio for, say, a postseason matchup with Phoenix.
2. Miami Heat
This would probably be the funniest possible outcome here. After trying and failing to acquire Lillard — in part, per reports, due to the Blazers’ disinterest in trading him to his preferred destination — would Miami actually pick up the phone and try to call up Joe Cronin and co.? The irony here is that Holiday could not be a more perfect fit on the Heat, and it would 100 percent be worth trying to figure something out. A deal built around Kyle Lowry’s salary and some of the picks they were willing to move for Lillard would be sensible, and while it would be a tough pill to swallow, maybe a promising young player like Nikola Jovic or Jaime Jaquez could help put their offer over the top.
Getting him in and letting him handle the point guard responsibilities makes life easier on Jimmy Butler (who wouldn’t have to shoulder such a gigantic role), Bam Adebayo (who would have a killer pick-and-roll partner), and Tyler Herro (who can just focus on being a scorer and secondary creator). And as an added bonus, he’d give Miami someone who could do as good a job as anyone guarding the guy Milwaukee just acquired, which, well, that’d be a fun subplot in a playoff series, wouldn’t it?
1. Philadelphia 76ers
Holiday is, obviously, a former Sixer. More importantly, Holiday could be the solution to the single biggest problem the team has right now, which is trying to find a way to get rid of James Harden while still being able to compete for a championship. While it’s certainly fair to wonder if Philly has any chance at accomplishing that following the moves Boston and Milwaukee made this summer, their best chance is probably turning Harden into a player who makes sense alongside Joel Embiid and Tyrese Maxey. If they’d need to give up Maxey here, that probably turns this into a non-starter, especially if they’d move him and keep Harden.
But imagine something like a three-team deal where Harden goes to the Clippers (or somewhere else), Holiday goes to Philadelphia, and both the Sixers and the team that lands Harden send Portland a first-round pick. (It’s very funny to imagine a two-team trade here with Harden and picks going to the Blazers, thereby letting them play this game with another guard.) But in terms of need, Philly laps the field, as Holiday gives them a solution to the Harden dilemma, is a terrific running mate alongside Maxey, and would be a great second fiddle to Embiid. It’d be difficult to pull this off, but they should certainly operate with the most urgency.
