Might a Jrue Holiday Sixers homecoming happen in the wake of the Damian Lillard trade?

Here we were, calmly going about our business and waiting for next week’s training camp, when the NBA went ahead and dropped a megaton bomb that would make Oppenheimer sit up and take notice. Damian Lillard is heading to Milwaukee, an Eastern Conference shake-up that surely doesn’t mean good things for the Philadelphia 76ers. However, in the wake of this league-shattering news, could there be a silver lining for the Sixers? Might Jrue Holiday be able to make his way back to the place where his NBA career started?

Reporting from PHLY Sports’ Kyle Neubeck says the Sixers are interested in making it happen:

Heading to Portland as part of the three-team Lillard deal, Holiday is clearly superfluous for a now-rebuilding Blazers team that has young guards Scoot Henderson, Anfernee Simons, and Shaedon Sharpe already on the roster. Reporting from ESPN’s Adrian Wojnarowski has the Blazers as open for business in the Jrue market:

Though on the tail end of his prime at age 33, Holiday is still a very helpful basketball player, averaging 19.3 points, 5.1 rebounds, and 7.4 assists last season, shooting 38.4 percent from behind the arc. He also made the 2022-23 NBA All-Defensive First Team, his fifth time earning All-Defensive team honors. Holiday would be a terrific fit alongside Tyrese Maxey in Philadelphia, able to play on or off the ball and share in the playmaking responsibility, while also taking the tougher defensive assignments with the ability to guard up.

Of course, any number of teams would love to have Holiday on their rosters. What would a trade look like to bring him to Philadelphia? Jrue is on the books for $34.95 million this year, with a player option for $37.365 million next year. A deal for Holiday would have to involve either Tobias Harris ($39.27 million cap hit) or James Harden ($35.64 million cap hit).

Trading Harden for Holiday would certainly be a brilliant stroke from Sixers President of Basketball Operation Daryl Morey. However, the Blazers would have no interest in him given their rebuilding status, glut of young guards, and (waves arms wildly) all the Harden stuff. A three-team deal with someone like the Clippers would be possible, but it would make more sense for Los Angeles to jump through fewer hoops to just bring Holiday into the fold, an arguably more impactful player than Harden at this stage of their careers anyway.

A more straightforward path might be Tobias Harris, who the Blazers could potentially value as an additional veteran presence to help set the tone for this next stage of the franchise’s development. Portland is too talented to bottom out completely, and the young guards, Jerami Grant, Tobias Harris, and Deandre Ayton is an interesting lineup this year, with flexibility next year when Harris comes off the books. The Sixers have their 2029 first-round pick available, and could throw in a pick swap or two. They could certainly put forth a competitive package, considering Portland will not have terrific leverage with teams knowing the need for them to move Holiday.

On the other hand, though, a Harris-for-Holiday trade would leave the Sixers’ roster unbalanced. Philadelphia is already pretty thin on the wings, and have Maxey and De’Anthony Melton set to play major minutes at the guard positions (not to mention if Jaden Springer is ready to make a leap or what Pat Beverley has left in the tank). It probably comes down to the resolution of the James Harden situation. If some sort of detente is reached, and Harden makes an effort to be a normal part of the team, I’m not sure how Holiday would fit into things. If Morey were to bite the bullet on a less-than-full-value Harden trade that brought back forward help, however, acquiring Holiday would be a tremendous way to avoid skipping a beat.

The additional thing that must be mentioned is that everything Morey has done this offseason has centered around the cap space plan next summer. Holiday’s player option next summer could throw a major wrench in those plans. So you also have to consider the probability that a Holiday move could obstruct an OG Anunoby signing (or your favorite 2024 free agent du jour).

Ultimately, Holiday would be a great on-court fit who is a tremendous individual off the court and has the added nostalgia factor of having played four seasons in Philadelphia. Still, the cap situation is slightly tricky, the Sixers aren’t exactly loaded for bear with trade assets, and the Harden saga has everything murky. It makes sense for the Sixers to be interested and make calls, and I’m sure Morey can cook up some more creative ways to get this done, but there’s not a no-brainer deal I see that makes Jrue Holiday a Sixer. Don’t let me stop you from dreaming and hitting the trade machine, though.