Well, it finally happened.
At long last, we finally got the Damian Lillard trade we've waited for since the night of the NBA Draft Lottery.
The Milwaukee Bucks made a big swing for Lillard to shock the NBA world and shake up the title landscape, shipping out Jrue Holiday with Grayson Allen and picks. The Suns made it a three-way deal, moving Deandre Ayton to Portland for Jusuf Nurkic and pieces.
Those are the principles in the blockbuster, and it's hard to imagine a trade shaking up the title race more on the cusp of the season. The Bucks became clear East favorites, with odds around +150 to +175 implying 36 to 40%, well ahead of the Celtics. The Suns got a slight bump in the West, with their win total creeping up and West odds just behind the Nuggets at around +300 to +350.
This deal will have a massive impact on the shape of the league, and on Bucks and Suns futures.
But I don't think the Bucks or Suns are the winners of the Damian Lillard trade — nor the Blazers, at least not this year.
The biggest winner of the Dame trade might actually be the team that ends up getting Jrue Holiday.
Jrue Holiday Is the Kingmaker Who Makes Every Good Team Better
Holiday is the consummate teammate, a leader who wins at every stop. You'd be hard-pressed to find anyone in the league with a single negative word to say about him.
Don't believe me? Holiday won the Twyman-Stokes Teammate of the Year award in three of the last four seasons — and in his one "off year," he won the NBA Sportsmanship Award instead. This dude is quite literally the teammate of the year, as chosen by his teammates and peers.
These days, everyone wants to team up with stars. Few players are clamoring to play with a guy like Holiday. But they should be.
Holiday is a star in his own right. He's not going to drop 40 very often and won't make many highlight reels, but he plays hard every night, defends the perimeter as well as anyone in the league, moves the ball well and fits just about any winning roster.
Some NBA stars are additive. Put someone like Brandon Ingram or Zach LaVine on your team and you'll add efficient scoring and raise a team's floor, without really moving the needle.
Holiday is multiplicative. The winning things he does — the defense, the hustle, all the "teammate" stuff — fill in all the gaps and makes the other guys around him even better. His presence lifts everyone else on the court.
Holiday is an NBA champion, and he had huge moments along the way and helped the Bucks get over the hump when they'd never even made the Finals with Giannis Antetokounmpo. Holiday is also an Olympic gold medalist, and he was an absolute core member of that team's identity as it struggled to find guard play and turned to Holiday to do all those little teammate things. He's five-time All-Defense selection too, and five is too low.
Beyond the on-court stuff, Holiday is a team culture superstar. He's the sort of guy whose quiet leadership sets the tone for an entire franchise. That sounds like hyperbole, but again, we literally have awards for this stuff and you can read all about what Holiday and his wife, Lauren, have done for their community and world around them.
I genuinely cannot imagine an NBA team that wouldn't immediately be improved significantly by adding Holiday. He's not going to lead his team in scoring and probably won't win Finals MVP, but he could be the kingmaker and help crown the real winner of this trade.
So who gets him?
Which NBA Teams Make Sense for a Jrue Holiday Trade?
So what NBA teams should be considering a Holiday trade?
Well, the Blazers already have him and the Bucks can't reacquire him yet, so … all 28 other teams?
Holiday turned 33 this summer, a month older than Lillard. He's entering the final year of his contract with $36.9 million remaining before a player option he'll likely decline. Any team trading for Holiday will give up so much that he'll have them over a barrel for any extension he wants to lock in after the season, since they can't risk losing him for nothing.
Of course, the trade has to make sense for Portland too. The Blazers don't want a point guard or a center. Scoot Henderson and Ayton are the future now. Portland also doesn't have any real use for old guys. This is the long game.
The Blazers covet youth and picks, and they'd love a great young wing to add to that core (along with Anfernee Simons and Shaedon Sharpe), but young wings don't exactly grow on trees, and the teams that have them are looking to keep them. That makes a deal difficult, but Holiday is a coveted piece that almost any team in the league should consider. He should be worth multiple firsts.
Shall we look at a few potential deals and what they could mean for bettors?
I'm just looking big picture, so don't worry too much about matching salaries and which picks. The teams can figure that stuff out. Let's just focus on imagining Holiday in a new uniform. I'm separating potential trade partners into a few groups. Let's start with the lesser fits — there's plenty of them — and hone in on the five most intriguing and how to prepare to bet them.
Long Shot Mentions
- Hawks — Atlanta gets a better defensive upgrade for Dejounte Murray and sends the younger player to Portland.
- Cavs — Moving Darius Garland or Jarrett Allen is intriguing but doesn't fit Portland. How about Donovan Mitchell? Too soon.
- Nets — Cam Johnson as a centerpiece? Maybe. More likely it has to mean the Blazers taking on Ben Simmons. Nah.
- Kings — Probably has to be built around Keegan Murray, plus Kevin Huerter and/or Harrison Barnes for salary? I don't see it.
- Raptors — Portland covets OG Anunoby, and Toronto needs a point guard with Fred VanVleet gone. A little too obvious?
Young Teams that Could Make a Leap with Holiday
- Pacers — Bennedict Mathurin, Buddy Hield, and pieces? I'm intrigued by Haliburton and Holiday with Indiana's new defensive pieces, but the timeline is off and the incoming Portland pieces don't really make sense.
- Timberwolves — How about Holiday for Mike Conley and Jaden McDaniels? Minnesota probably doesn't give up its young wing but Holiday and Rudy Gobert on defense with Anthony Edwards and Karl-Anthony Towns on offense could give the Wolves a genuine shot at the Finals, and it's hard to imagine Portland getting many better single young player assets.
- Magic — Would Holiday come in to set team culture and act as a leader, raising the floor for a playoff push and giving this young team a lead guard for the first time in forever? Maybe Portland returns Gonzaga's Jalen Suggs to the Pacific Northwest, perhaps Cole Anthony or Markelle Fultz, plus a pick and effectively expiring deals in Jonathan Isaac, Gary Harris and/or Joe Ingles?
- Nuggets — Would the champs dare trade Michael Porter Jr. for Holiday? It would be a huge shake-up, but MPJ is an expensive luxury who didn't always play in the big moments, and Holiday replaces the expiring Kentavious Caldwell-Pope role and adds defensive tenacity, leaving Denver to save some cash and find wings like Christian Braun or Julian Strawther for that MPJ 3-and-D role. Porter would be a huge injury risk for Portland, but he played high school ball in the Pacific Northwest and has star upside.
- Pelicans — Would New Orleans trade Brandon Ingram for Holiday? Portland might have to add something, but it could be a winner for both teams. The Blazers get a young All-Star and face of the franchise. The Pels bring Holiday back as a perfect fit next to C.J. McCollum and add Holiday to the other nasty defenders around McCollum, Zion Williamson and Jonas Valanciunas. Ingram might be too starry of a name to trade away, but McCollum and pieces doesn't make sense for Portland. A straight Ingram swap might be my single favorite fit on the board.
Intriguing Fits But Hard to Find the Deal
- Mavericks — I'd absolutely love to put Holiday next to Luka Doncic and Kyrie Irving, but good luck finding the right deal. Unless Portland covets Jaden Hardy, Josh Green and/or Dereck Lively, there's just not much here. Dallas's matching salaries in Tim Hardaway Jr., Richaun Holmes and Maxi Kleber are negative assets, and the Mavs can only really trade the 2027 pick. It's not enough.
- Celtics — Holiday would be a perfect Marcus Smart replacement, and the team would love to have him in a Bucks playoff matchup to defend Lillard. Boston was a trade loser since the Celtics don't really have a defensive answer for either Milwaukee star now. But what's the deal? It's got to be Malcolm Brogdon and either Al Horford or Robert Williams to make the salary work, plus picks. I'm not sure the Celtics can risk giving up either big man, and it's hard to see this tempting Portland.
- Lakers — A Lakers deal probably has to wait until December 15, and the cupboard is pretty bare. Unless LA trades Austin Reaves, the offer is probably D'Angelo Russell, Rui Hachimura and a 2029 pick. When you see the other options on this list, it's hard to imagine that being anywhere near Portland's best offer. But LA could benefit secondhand. If a Holiday deal involves a veteran point guard like Kyle Lowry or Chris Paul as makeweight salary, the Lakers might be No. 1 on any buyout market. A veteran PG like that could be a real difference maker, worthy to consider title odds.
The Five Most Intriguing Jrue Holiday Fits — and How to Bet Them
- Thunder — The Thunder have a ton of cap room and assets and could go get Holiday as sort of a pre-free agency swing to cash in some of those assets and accelerate the timeline. Maybe that's an offer built around Josh Giddey, but he'd have to play with Henderson. It could be Lu Dort as a young wing, plus Davis Bertans' salary and some picks, a package that makes some sense for Portland. Can I interest you in a Jrue, Shai Gilgeous-Alexander, Jalen Williams and Chet Holmgren lineup? Oh baby. Could that team contend in the West this year? The bet here is Gilgeous-Alexander to win MVP, if Holiday's arrival raises the defense and makes the Thunder a top-four seed.
- Heat — These teams are probably done with each other at this point, but hilariously, the same offer Miami did or didn't make for Lillard could also work for Holiday. He'd be an amazing Heat Culture fit with all his intangibles and defense, allowing the Heat to double down on its identity and strength, and I'd probably make Bam Adebayo the new DPOY favorite.
- Warriors — We've seen Holiday-Ws rumors. How about Jonathan Kuminga and Chris Paul? CP3 is an expiring deal, and Kuminga is young and talented and fits Portland's build. Klay Thompson or Moses Moody could be options, too. The Warriors add Holiday to replace Thompson's waning defense, a stellar fit that would make this defense nasty with Draymond Green. The fallout here is twofold. I'd look hard at Warriors title odds with Holiday, but this deal likely also sends CP3 to the buyout market, which could deliver him for free to the Clippers or Lakers and increase their title odds too. Speaking of which…
- Clippers — If Portland just wants to get picks and clear salary, the Clippers might actually have the best available deal. LA can offer its 2028 and 2030 picks plus expiring deals in Nicolas Batum, Robert Covington or Marcus Morris Sr. to match salary. Terance Mann is the only notable young name, but just getting expiring deals and picks essentially nets the team five firsts for Lillard while clearing the books. The Clippers have badly needed a lead playmaker. Is that Holiday? It could be, or it could also open the door for a three-way trade with…
- 76ers — I'm not sure there's a direct deal for Holiday. Maybe something like Tyrese Maxey and Tobias Harris, and Philly likely doesn't give up Maxey, as intriguing as a James Harden-Holiday-Joel Embiid trio might be. But the Sixers might be the right third team. Harden goes to the Clippers like he wants, Holiday comes to Philly as an ideal fit next to Maxey and Embiid, and the Blazers get those Clippers picks, maybe even a Sixers pick. That's a pretty good outcome for all three teams. The Clippers and Sixers move up in their respective conference pecking orders. I can't get there on title odds for either, but I'd be all over a Maxey ticket for Most Improved Player.
So that was 18 teams — literally 60% of the league. Holiday is that good and makes sense to that many teams, and some fans will read this and wonder why their team wasn't included too.
Lillard is the headliner on Wednesday's blockbuster trade, and Bucks and Suns title odds definitely shifted. But Holiday might be the kingmaker when all is said and done and determine the real winner of the trade in the end. Be ready to act.
