After months of negotiations, the Portland Trail Blazers have pulled off a massive blockbuster three-way trade with the Milwaukee Bucks and Phoenix Suns, sending out Damian Lillard, Jusuf Nurkic, Nassir Little and Keon Johnson to get Jrue Holiday, DeAndre Ayton, Toumani Camara, a 2029 unprotected first-round pick (via Milwaukee) and the right to swap picks in 2028 and 2030 in return.

One of the newest members of the Blazers organization shouldn't unpack just yet, however, as the Blazers would be wise to flip and re-trade Jrue Holiday to a contender for youth and draft picks, maximizing the return for Lillard and starting a rebuild in earnest as opposed to keeping an unhappy 33-year-old point guard on the roster yet again.

Here are the three main reasons the Blazers should trade Jrue Holiday after the Bucks/Suns/Blazers blockbuster deal:


1. Jrue Holiday can start a bidding war

It's a little odd to see the Blazers trade their 33-year-old point guard in Damian Lillard just to get…another 33-year-old star point guard in Jrue Holiday. But the reality of the situation for Portland was that trading Lillard to a contender for youth and valuable picks was always going to be a difficult proposition and that acquiring someone to re-trade was a more realistic path. Holiday is going to be much more attractive on the trade market than, say, Tyler Herro, because his contract isn't oppressive (Holiday has a player option for 2024-25) and his defense-first mentality can fit in with just about any title contender.

Holiday, as we've seen, is the perfect third option on a title team as someone who can score but isn't necessarily relied on for that. His ability to provide value both on and off the ball is perfect for a team in need of help in the backcourt but not wanting to fork over all the possessions that a score-first type guard necessitates.

Holiday's short contract should be easier for teams to acquire than Lillard's, and while he's not on the same star level as Dame, Holiday can still start a bidding war on the trade market for teams in win-now mode. The Boston Celtics, Miami Heat, Los Angeles Clippers, and Los Angeles Lakers all make sense as potential trading partners for the Blazers, who can continue to re-flip pieces from subsequent trades to get the draft pick and young player haul that was going to be difficult to get in a singular trade with a contender.


2. Jrue Holiday would impede Scoot Henderson's development

By re-trading Jrue Holiday, the Blazers can clear the decks and the ballhandling responsibilities for Scoot Henderson and Anfernee Simons, who should be considered the backcourt of the future in Portland. While Holiday could fit with those two young players given his ability to guard multiple positions, Henderson needs to get as many on-ball reps as possible and become “the guy” from Day 1 in Portland.

It's mutually beneficial for both sides to quickly part ways. Holiday should be competing for championships at this stage in his career, and he has nothing to gain from babysitting the Blazers young backcourt for a season. Battling for lottery position is beneath Holiday at this point, and even the chance at having an unhappy veteran around should be avoided during Portland's rebuild. Portland, knowingly or unknowingly, leaned into being young, fun, and well, bad, once Damian Lillard was traded. Getting Holiday back in the trade shouldn't change that, as this needs to be Henderson's team right away now.

That's not to say that Henderson and Simons couldn't learn plenty of valuable lessons from Holiday, but the risk associated with keeping Holiday (injury, trade demand, etc.) greatly outweighs the reward. Clear the touches and minutes for Henderson, and live with the results.


3. The Blazers can't compete and need a full rebuild and youth movement

Perhaps it would be different if the Blazers could realistically compete for a title, but that's not where this current roster is at. Yes, Ayton is an upgrade over Nurkic and could shine as a key offensive focus after playing third fiddle to Devin Booker and Chris Paul/Kevin Durant for so long, but the Western Conference is loaded and the Blazers don't have the true star power or depth needed to go deep in the playoffs.

Everything now should be in service of building a team around Henderson for the future. That can be done by acquiring draft picks and players on controllable rookie deals, and trading Holiday is Portland's best shot at getting more of those lottery tickets.  Portland should have no delusions about contending in a loaded Western Conference — start the youth movement in earnest, get a great offer for Holiday, and be ready to run the West four years from now rather than staying on the treadmill of mediocrity the team was stuck on with Damian Lillard the past five plus years.

This is a new day for the Blazers after the three-way deal with the Bucks and Suns, and trading Holiday is a must if Portland wants to truly build a contender down the line.