When it came to determining whether the Portland Trail Blazers had won or lost the Damian Lillard deal, I went with TBD. We do not yet know.
Portland came out on top in the straight-up trade with Milwaukee, but a big part of that was receiving All-Star point guard Jrue Holiday, who the Trail Blazers are already trying to move. The return on the Holiday transaction will allow us to declare Portland victors (or losers) in the Lillard trade.
According to Jared Weiss of The Athletic, the cost of acquiring Holiday will begin with two first-round picks and matching compensation. According to Barry Jackson and Anthony Chiang of the Miami Herald, Holiday has six favored teams.
According to the Miami Herald, Holiday is interested in the Miami Heat, Los Angeles Clippers, Los Angeles Lakers, Boston Celtics, Chicago Bulls, and Philadelphia 76ers.
More clubs will be interested, and Portland general manager Joe Cronin should and will take the best offer for his team, regardless of Holiday’s intentions, but contenders should be the most motivated in acquiring Holiday. Let’s take a short look at Holiday’s six teams.
Miami Heat: They didn’t get Lillard, but Holiday would be a good consolation prize, suit the culture, be a good point guard for them, and keep them as serious title candidates. Miami has the selections and salaries if they are willing to include them in the deal, but after the Lillard debacle, will Cronin even answer the phone if it is from the 305 area code?
The Miami Herald says that the Heat have no plans to pursue a trade for James Harden.
Los Angeles Clippers: The Clippers had negotiations this summer about trading for James Harden, but Holiday would be a better fit (and why would Los Angeles execute a three-way trade to obtain Harden when dealing for Holiday straight up would be cleaner). Los Angeles may include a draft selection or two, salary filler (for example, Marcus Morris Sr. and Robert Covington), and young players like Amir Coffey and Bones Highland. The Blazers may prefer a third team to take on the large contracts, but they are set to expire. Would Los Angeles accept Terrance Mann if Portland asked for him?
Los Angeles Lakers: The Lakers can’t make this trade until after December 15 because they can’t trade anyone they signed or extended this summer, so D’Angelo Russell, Rui Hachimura, Gabe Vincent, and others are off the table for the time being, and the Lakers’ only way to match salary is to send out Anthony Davis. Which is plainly a dead end.
Boston Celtics: The Celtics can make this trade work by sending away Malcolm Brogdon (who they were willing to trade all summer) along with one of Al Horford or Robert Williams III, as well as choices. Portland may want a third team to take on the veterans, but Boston can keep Horford and Williams and use a combination of lower-cost players and a trade exception from the Grant Williams deal to get it done, as Weiss at The Athletic points out. Would Boston be willing to give up two first-round picks to make this happen?
With Lonzo Ball sidelined for the season, the Chicago Bulls might benefit from a two-way glue point guard like Holiday. Chicago has been looking for a possible Zach LaVine deal all summer, but Portland isn’t going to want to bring LaVine in with their youthful core (and they don’t want to bring LaVine in simply to flip him in another trade). Financially, a trade including DeMar DeRozan and Alex Caruso makes sense, but the Bulls and Blazers are unlikely to be interested. There doesn’t appear to be a trade that benefits both parties.
Philadelphia 76ers: This only works if the Sixers can include a trade for James Harden in the transaction. Portland doesn’t want Harden (and he wouldn’t want to go there), and this summer has demonstrated that there isn’t much of a market for an All-Star guard. Philly is interested in Holiday, but it’s difficult to see a trade coming together (unless they can push the Clippers into a three-way deal with Harden going to his preferred Los Angeles).
Other teams will be competing. The Warriors, for example, could join in the fun by selling Chris Paul and Jonathan Kuminga for a pick or two, but I’m not sure either side would enjoy that setup (and if you thought the “bring CP3 off the bench” conversation was contentious, wait till you hear about Holiday).
All of this indicates that the cost of Holiday will be significant. As a result, Portland comes out on top.