When it came time to call the Portland Trail Blazers a winner or a loser in the Damian Lillard trade, I went with TBD. We don't know yet.
Portland came out a winner in the straight-up trade with Milwaukee, but part of that win was getting All-Star point guard Jrue Holiday, who the Trail Blazers are already working to flip in another deal. The return on the Holiday trade will let us call Portland winners (or not), in dealing Lillard.
The price to land Holiday reportedly will start with two first-round picks, plus matching salary, reports Jared Weiss at The Athletic. Holiday has six teams that are his preferred destinations, reports Barry Jackson and Anthony Chiang at the Miami Herald.
Sources tell the Miami Herald that the Miami Heat, Los Angeles Clippers, Los Angeles Lakers, Boston Celtics, Chicago Bulls and Philadelphia 76ers are teams that appeal to Holiday.
More teams than that will be interested, and Portland GM Joe Cronin should and will take the best offer for his team with little regard for Holiday's wishes, but it is contenders that should be the most invested in landing Holiday. Let's do a quick breakdown of Holiday's six teams.
Miami Heat: They missed out on Lillard, but Holiday would be a quality consolation prize, would fit the culture and be a quality point guard for them, and would keep them as serious title contenders. Miami has the picks and salary if they are willing to put them in the deal, but after the Lillard trade mess will Cronin even pick up the phone if the call is from the 305 area code?
We should add the Heat have no intention of trying to deal for James Harden, the Miami Herald reports.
Los Angeles Clippers: The Clippers had discussions around landing James Harden in a trade this summer, but Holiday would be a better fit (and why would Los Angeles do a three-way trade to get Harden when dealing for Holiday straight up would be cleaner). Los Angeles could throw in a pick or two, salary filler (Marcus Morris Sr. and Robert Covington, for example) plus young players such as Amir Coffey and Bones Highland. The Blazers may want a third team to take on the big contracts, but they are expiring. Portland might ask for Terrance Mann, would Los Angeles throw him in?
Los Angeles Lakers: The Lakers cannot make this trade until after Dec. 15 because they can't trade anyone they signed or extended this summer yet, so D'Angelo Russell, Rui Hachimura, Gabe Vincent and others are off the table for right now, and the only way the Lakers match salary is sending out Anthony Davis. Which is obviously dead in the water.
Boston Celtics: Boston can make this trade work by sending out Malcolm Brogdon (who they were open to trading all summer) plus one of Al Horford or Robert Williams III, plus picks. Portland might want a third team involved to take on the veterans, or Boston can keep Horford and Williams and use a combination of lower priced players and a trade exception from the Grant Williams deal to get it done, as Weiss notes at The Athletic. Would Boston be willing to throw in two firsts to make this happen?
Chicago Bulls: With Lonzo Ball out for the season, the Bulls could use a two-way glue point guard like Holiday. Chicago has looked for a possible Zach LaVine trade all summer, but while that works financially Portland isn't going to want to bring in LaVine with their young core (and they don't want to bring in LaVine just to flip him in another trade). Financially, something like DeMar DeRozan and Alex Caruso works, but it's hard to see that trade appealing to the Bulls or Blazers. There just doesn't seem to be a trade that works for both sides.
Philadelphia 76ers: This only works if the Sixers find a trade for James Harden as part of the deal. Portland doesn't want Harden (and he wouldn't want to go to Portland) and this summer has shown there isn't much of a market for All-Star guard. Philly is interested in Holiday, but it's hard to see how a deal works (unless they can talk the Clippers into a three-way with Harden going to his preferred Los Angeles).
Other teams will be in the mix. For example, the Warriors could get in on the party by trading Chris Paul and Jonathan Kuminga plus a pick or two, but I am not sure either side would like that construction (and if you thought the "bring CP3 off the bench" talk was controversial, what do you do with Holiday).
What is clear from all this is the price for Holiday will be high. Which means in the end Portland is a winner.