After months of scrolling through countless Damian Lillard trade rumors, the news finally broke on Wednesday afternoon that the Portland Trail Blazers' long-time franchise cornerstone was headed to the Milwaukee Bucks. In one of the more surprising blockbuster trades in recent memory, the seven-time All-Star guard will pair with Giannis Antetokounmpo to form one of the best duos in the league. 

Now, the new big fish in the trade market is none other than the player Lillard was dealt for: Jrue Holiday. The Blazers' return featured Holiday, former No. 1 pick Deandre Ayton, Phoenix Suns second-rounder Toumani Camara, an unprotected Bucks 2029 first-rounder, and 2028 and 2030 first-round pick swaps from Milwaukee. The circumstances of Lillard’s trade request and his desire to be dealt specifically to the Miami Heat dampened his trade value, but the Blazers were able to come away with a “palatable” return.

However, Holiday is unlikely to stay in Portland for long as he does not fit their rebuilding timeline around core players Scoot Henderson and Shaedon Sharpe. ESPN’s Bobby Marks graded Portland’s trade return as “incomplete” pending the potential assets the team receives for Holiday when they flip him.

Many contending teams are reportedly rushing to the phones to make moves in reaction to the Lillard blockbuster, with several expressing serious interest in Holiday. These possible suitors include the Philadelphia 76ers, Boston Celtics, Los Angeles Clippers and Heat. Teams must factor in Holiday's potential free agency next summer and the possibility of signing him to a long-term extension, which he becomes eligible for on Feb. 22. Perhaps the Blazers will have some urgency to deal Holiday prior to Media Day on Oct. 2 in order to avoid questions and logistics about bringing him in for training camp. 

For any team over the luxury-tax apron ($171,294,000) to trade for Holiday, they need to trade away at least $33,175,536 (90% of Holiday’s 2023-24 salary) in salaries in order to legally execute a trade. The rest of the league will only need to send out $27,646,280 (75% of Holiday’s 2023-24 salary) in order to make a deal. 

Another important CBA note with any Holiday trade is that his $36,861,707 salary cannot be aggregated with other contracts for two months. While Holiday is still eligible to be immediately rerouted elsewhere, he cannot be traded with other players. For example, just a few months back, Chris Paul was traded to the Washington Wizards and then quickly rerouted in a separate deal to Golden State. Because Paul was the only salary going back to the Warriors, he was legally allowed to be traded. This must be taken into consideration when proposing potential trade ideas.

With Holiday potentially on the move in the coming days, let’s take a look at some potential deals for the 33-year-old.

Realistic Trade Destinations

BOSTON CELTICS

Celtics receive: Jrue Holiday

Trail Blazers receive: Malcolm Brogdon, Al Horford, Dalano Banton (salary guarantee increased to $1,009,853 to satisfy trade rules), 2024 GSW top-4 protected first-round pick, 2025 BOS first-round pick, 2026 BOS first-round pick swap, 2024 CHI/DAL/NO (most favorable) second-round pick, 2026 MIN/NO/NYK/POR (most favorable) second-round pick

By trading away Marcus Smart this summer, the Celtics lost the key cog to their juggernaut defense. Despite not having a Defensive Player of the Year award, Holiday would probably serve as an upgrade to Smart on both the offensive and defensive ends of the floor, helping the Celtics compete against the new-look Bucks in the East. If they wish to enter the Holiday sweepstakes, they would need to trade Malcolm Brogdon ($22,500,000), whom they were close to dealing to the Clippers in July. Along with Brogdon, they would have to sacrifice either Al Horford ($10,000,000) or Robert Williams III ($11,571,429) to make the salaries work. They have all of their own draft picks to trade as well as the Golden State Warriors' pick in 2024, which they got from the Smart trade.

MIAMI HEAT

Heat receive: Jrue Holiday

Trail Blazers receive: Kyle Lowry, Nikola Jovic, Haywood Highsmith, 2027 MIA first-round pick, 2029 MIA top-14 protected first-round pick, 2028 MIA first-round pick swap, 2024 MIA top-50 protected second-round pick, 2026 LAL second-round pick, 2027 HOU/IND/MIA/OKC/SA (least favorable) second-round pick

Missing out once again in their pursuit of a star third option to pair with Jimmy Butler and Bam Adebayo, Miami could use an upgrade like Holiday to their seemingly incomplete roster. Holiday would provide a must-needed scoring punch and would fit seamlessly in Miami’s hard-working culture. While their Lillard trade package was highlighted by Tyler Herro, they likely wouldn’t use him in any trade for Holiday. Their salary going out in a deal would come from Kyle Lowry’s expiring salary ($29,682,540) and some combination of younger players like Jaime Jaquez Jr. ($3,510,533), Nikola Jovic ($2,352,000) and Haywood Highsmith ($1,902,137). While they are somewhat restricted in terms of draft assets, they can offer up to three first-round picks if they amend their 2025 first-round pick they owe the Oklahoma City Thunder. They have three second-rounders to offer as well. 

NEW YORK KNICKS

Knicks receive: Jrue Holiday

Trail Blazers receive: RJ Barrett, Reggie Bullock, Khem Birch, 2024 DAL top-10 protected first-round pick, 2024 DET top-18 protected first-round pick, 2024 WAS top-12 protected first-round pick

Spurs receive: Evan Fournier, 2026 MEM top-42 protected second-round pick, 2027 NO/POR (less favorable) second-round pick

The Knicks may be holding out for when the next superstar – i.e. Joel Embiid, Donovan Mitchell or Giannis Antetokounmpo (although maybe not anymore?) – asks for a trade. While New York may be focused on further down the line, acquiring a player like Holiday could allow them to boost their roster right now without giving up enough capital to harm their future superstar pursuits. A Knicks trade that would not harm their trove of draft assets would have to send out RJ Barrett ($23,883,929), who potentially fits Portland’s rebuilding timeline. Jrue could line up as the team’s starting shooting guard alongside Jalen Brunson, while Josh Hart would play more minutes at small forward to mitigate the loss of Barrett. Evan Fournier’s large salary ($18,857,143) would also have to be in any deal for the Knicks to take in Holiday. Portland wouldn’t want to acquire both Fournier and Barrett as that would push them over the luxury tax, therefore they would likely route Fournier to another team (like San Antonio).

LOS ANGELES CLIPPERS

Clippers receive: Jrue Holiday

Trail Blazers receive: Marcus Morris Sr., Robert Covington, Amir Coffey, Jason Preston (salary fully guaranteed), 2028 LAC first-round pick, 2030 LAC first-round pick, 2029 LAC first-round pick swap

The Clippers may have been given an olive branch with a player like Jrue Holiday becoming available, as he's an impact player at a price they can afford. It also provides an alternative for the Clippers to land a third star while avoiding the potential drama/issues that could come with acquiring a player like James Harden. The Clippers have a lot of high-salary veterans they could use to get to Holiday’s number like Norman Powell ($18,000,000), Marcus Morris Sr. ($17,116,279), Nicolas Batum ($11,710,818) and Robert Covington ($11,692,308). They would probably like to keep Terance Mann, who they seem to not want to include in a potential Harden trade, although his $10,576,923 could be useful. Portland could view their unprotected picks in 2028 and 2030 as some of the best draft assets they could receive due to their aging stars and lack of postseason success.

PHILADELPHIA 76ERS

76ers receive: Jrue Holiday

Clippers receive: James Harden, 2024 NYK second-round pick, 2029 PHI second-round pick, 2030 PHI second-round pick

Trail Blazers receive: Marcus Morris Sr., Robert Covington, Amir Coffey, Jason Preston (salary fully guaranteed to satisfy trade rules), 2028 LAC first-round pick, 2029 PHI first-round pick, 2029 LAC first-round pick swap

Amidst the James Harden debacle, Daryl Morey has remained steadfast in getting a formidable return if they choose to trade the disgruntled All-Star. A reunion with Jrue Holiday, who played in Philadelphia from 2009 to 2013, certainly should get Morey and the Sixers' attention. Holiday would certainly upgrade their defense while being a good support and influence on Tyrese Maxey. The Trail Blazers would have little interest in taking a direct package from Philadelphia, which would almost certainly be headlined by Harden ($35,640,000). Harden's desired destination, the Clippers, should still be interested in acquiring him, but may be more interested in trading for Holiday directly. Portland would likely get a similar package to what they would receive if they traded directly with the Clippers, potentially leaving Philadelphia out to dry. The Sixers would have to incentivize the Clippers by trading some draft capital to take Harden instead of Holiday.

Honorable Mentions

GOLDEN STATE WARRIORS

The Warriors are a logical Holiday destination in terms of fit and trade assets. A trade package would have to send the newly acquired Chris Paul back to Portland or a third team along with a young player like Jonathan Kuminga, Moses Moody or Brandin Podziemski, plus a draft pick. Given that coach Steve Kerr has talked all summer about bringing Paul into the fold, it would be pretty surprising if the team pivoted from the future Hall-of-Famer just before training camp. If the Warriors do choose to jump in the Holiday waters, they could quickly move to the front of the line. 

TORONTO RAPTORS

Toronto was considered the favorite to acquire Lillard at one point, with a package that was likely headlined by OG Anunoby and draft assets. In order to acquire Holiday, they would need to use a similar package, albeit with less draft capital involved. It seems as though the Raptors were being coy about potentially dealing Anunoby for Lillard, according to Ryan Wolstat of the Toronto Sun. If Masai Ujiri was unwilling to include Anunoby in trade discussions before, it’s unlikely he will do so for a player like Holiday. 

MINNESOTA TIMBERWOLVES

Holiday would be a near perfect fit alongside Anthony Edwards in the Wolves' backcourt and would greatly improve their defense. However, Minnesota simply doesn’t have the right salaries or draft assets to realistically get to Holiday’s number unless they are willing to part ways with Karl-Anthony Towns. Even if Tim Connelly was willing to deal Towns for Holiday, the trade may not be what Portland is looking for with the 2015 No. 1 overall pick’s five-year supermax extension beginning next season. The idea of paying supermax money to Towns will likely be a turn off for Blazers GM Joe Cronin.

ORLANDO MAGIC

Orlando is probably the most fun dark-horse destination for Jrue. While Markelle Fultz has been a suitable lead guard when healthy, Holiday would bring a championship-level veteran presence that could be useful for Orlando’s young squad. The question with the Magic is whether they would actually pursue a deal that would accelerate their timeline with Paolo Banchero and Franz Wagner, as well as whether they would part with draft capital that they could potentially use down the line in future trades.