How the Damian Lillard trade to Milwaukee could benefit the Sixers

Giannis Antetokounmpo and Damian Lillard teaming up in Milwaukee is a prospect that most NBA fanbases are scared of. Lillard has the defensive cover he has always needed, and Giannis has the crunch-time offensive force he could have used to escape hairy playoff situations in the past. And Sixers fans, down bad as it is, are ready to punt the 2023-24 season entirely as they think about Philadelphia attacking this problem.

I’m here to tell you it may not be all bad news for the Sixers, who could end up benefitting from the Damian Lillard trade in some form or fashion.

You must be crazy

I am not. But for you to stay with me, I need you to accept these ideas as something close to fact.

• The Sixers were unlikely to be the team that acquired Lillard. While they were more involved than the team let on, there was never any indication they would bid top dollar for Lillard and throw Tyrese Maxey into the trade rumor mill.
• The Sixers would have been in a worse short-term position if Miami had acquired Lillard. They are certainly underneath the top tier of the conference, comprised of Milwaukee and Boston at the moment. But the Sixers would have been trailing that duo regardless, and in a world where the Heat acquired Lillard, Miami would have been a firm Tier 1 team in their own right. Simple math here, but it is better to have two definitively better teams in the conference rather than three.

There will be pushback on the second point as a result of Miami’s playoff success, and the Heat are and have been a better playoff team than the Sixers. That’s inarguable. However, Miami had a similar offseason to the Sixers in that they were essentially in a holding pattern that required one big move to justify, and now they’re left in a tough spot.

The Heat let their two biggest free agents (and two big playoff contributors) walk, put Tyler Herro in the store window like a prized cut of ham, and did nothing of consequence in free agency. Without a big step forward from one of their young guys — never underestimate Heat Culture voodoo magic, of course — they are on track to be worse after barely scraping by to make the playoffs in the first place.

If we can agree on those things, let’s move into the abstract.

The arms race begins

As long as Lillard was on the trade block, any team with even remote star trade interest was going to put that on hold. The Chicago Bulls and Toronto Raptors illustrated that point beautifully — neither would have had any realistic title chance trading for Dame, yet both popped up as suitors for the star guard at points over the last couple of weeks.

(The Raptors, it seems, really fumbled the bag on this one. There are people more plugged in than I am in Toronto, but the word in league circles was that Masai Ujiri could have had this deal done a week ago if the Raptors had been willing to part with OG Anunoby.)

Fear is a powerful motivator, and while the old Bucks were respected, you wouldn’t say they scared anyone, as Jimmy Butler and Co. were able to show in round one last year. Lillard jumping to a true blue contender changes that. It’s an, “Oh, shit!” transaction that will make a lot of executives wonder if they have enough.

The Heat are happier than any team in the NBA to Maguyver a problem, so maybe they just put their heads down and we wake up one day to Nikola Jovic being a star. But with Butler publicly accusing the Bucks of tampering (jokingly or not) and the Heat not so subtly whining through the media about the Blazers for the last two months, they do not have the feel of a franchise satisfied with what they have.

How do the Boston Celtics feel right now? Perhaps it was still the right time to move on from Marcus Smart after a long partnership with him and plenty of headbutting internally. But his defensive tenacity on the perimeter would have been more valuable than ever in a matchup with the Bucks. They probably feel better about their ability to attack Milwaukee using their star wings, but worse about their ability to defend the Lillard/Giannis pick-and-roll.

Go further down the list to Cleveland, who made a splashy trade for Donovan Mitchell last offseason only to get punked in round one by the Knicks. There is a fair bit of pressure to win before Mitchell can opt out of his deal in 2024-25. The Bucks leveling up through this trade will warrant some soul-searching for the Cavs as to what their next move is.

None of these things mean the Sixers are feeling great, obviously, as the rest of these teams all ostensibly have stars who currently want to play for them. Philadelphia still has the biggest active problem to solve. But this trade adds pressure on any win-now team, perhaps even creating a bit of desperation. And desperation tends to heat up the trade market, which would be a godsend for a Sixers team in need of more moves.

It’s not unfathomable that the market for Harden could expand at this point. I would doubt he fits into anyone’s idea of “Heat Culture” but he still represents a unique opportunity for any team looking for guard help — Harden played at a high level last season as a No. 2 to Embiid and has shown he can still be an impact player as a co-star after injuries slowed him down.

Failing that, if a motivated Harden can be convinced to come back to Philly, Milwaukee now has a dead-meat defender as the tip of the spear. Yes, Lillard has great help behind him, but switch hunters will rejoice at the idea of seeking out Lillard in crunch time. With Milwaukee’s best defensive players now all best at help defense and rim protection rather than switching, an iso-heavy player like Harden might find even more joy against the Bucks.

A Jrue Holiday reunion will be the focus for Sixers fans right now but think of all the teams who felt they needed to go in for Lillard: Miami, Milwaukee, Toronto, Boston, New Orleans, Minnesota, Chicago, and Philadelphia were all known to have some level of interest in Lillard.

Many of the players on those teams, Zach LaVine and Tyler Herro for example, have been the subject of constant rumors all summer. Can their current teams get them to buy in again, or is a non-Lillard trade the way forward? There are notable future free agents on those teams as well. To pick a name out of the list, how available is New Orleans’ Brandon Ingram?

With the focus off of Lillard, the door is open for Philadelphia to make some noise in the trade market.

The Holiday element

As we reported at PHLY Sports shortly after the Lillard trade went down, the Sixers are interested in trying to acquire Jrue Holiday from Portland. ESPN’s Bobby Marks took this a step further on an episode of The Lowe Post on Wednesday evening, claiming that a Holiday/Sixers reunion in free agency next summer had already been whispered about.

Philly is interesting [as a trade destination]. There have been rumors about Holiday in Philly as a free agent, and if he got to free agency here, does Philly go — is that a three-teamer? Certainly not going to trade Maxey for Holiday, that doesn’t make sense here. Does that involve Harden now? I think that’s intriguing in itself.

Lowe Post, ESPN

I won’t sit here and tell you that acquiring Holiday gives them better title odds than pushing chips in for Lillard would have. That being said, Holiday is a trade option that was basically nonexistent until 24 hours ago, as the Bucks were not going to make him available to Philly for basically any offer. He represents a middle ground between holding out for a star and swapping Harden out for a series of role players. The best part is not that you could retain Maxey in a Holiday trade, but that Maxey and Holiday are a hand-in-glove fit on several levels.

While the Harden/Maxey pairing has electric offensive potential, their defensive problems are numerous. Even as he ages, Holiday would represent a significant defensive upgrade over Harden, a chess piece you can move around to take top assignments and take pressure off of their other players. He would not, mind you, be a replacement for Harden’s playmaking and the ability to carry an offense for long stretches of time. That responsibility would need to be spread across several players, and certainly to Embiid as the hub of the team. Still, Holiday is coming off of three straight good outside shooting seasons and had his best-ever year there last year when you factor in volume.

(I know, I know, the playoff numbers have been ugly in recent seasons. A problem to worry about at a later date.)

Suddenly, the Sixers would have some switch-heavy lineups to throw at teams and disrupt a game with. You could throw a backcourt of Holiday/Melton out there in bench groupings, sprinkle in some wing athletes (Kelly Oubre, Danuel House Jr., Tobias Harris), and either have Embiid anchoring the backline or Paul Reed’s brand of chaos out there. Hell, I’d argue there’s a decent amount of intrigue pairing Holiday with Jaden Springer off of the bench, provided you can find enough shooting to make that work.

The point is that he fits with basically anyone you can think of. And that’s doubly true if his shooting numbers hold, as Holiday would be a reliable off-ball threat who you can trust as an initiator as well. Playing in an Embiid-centric world wouldn’t be that different from playing in the Giannis-centric world he thrived in.

That fact is why he won’t come cheap, mind you. Tobias Harris has been floated by Sixers fans as a guy to flip in exchange for Holiday, and though their contracts are very similar for matching purposes, I don’t know why Portland would make a deal for Harris unless you found a way to acquire additional draft capital elsewhere. The Blazers will have a lot of suitors for Holiday’s services, many of whom will have younger players to offer, more picks to offer, or both. So it does seem more likely that Holiday would have to be part of a multi-team Harden deal that sends him to L.A.

(Don’t discount the Clippers cutting out the middleman and chasing Holiday over Harden. Holiday is an L.A. native who might end up being a better fit for what the Clippers want/need.)

In any case, there is mutual interest between Holiday and the Sixers for a potential reunion. And that possibility would not have been possible until at least next summer without this Lillard trade.

A moment of clarity

There are two ways teams can go when faced with a potential NBA juggernaut: submission or defiance. We have seen Daryl Morey go with the latter option in the past, loading up to try to compete with the Kevin Durant Warriors and nearly finding a way to outlast them. I would be stunned if the Sixers simply threw up their hands and decided they were uninterested in trying to keep up over the next couple of years because it got slightly harder to win in the East.

This next year or two was already expected to be wild for NBA transactions after changes to the CBA, and I think the Lillard trade might accelerate that reality. Teams on the fringe may decide to get out while the gettin’ is still good. If nothing else, this move should be a wake-up call for Philadelphia, a reminder that the teams above and around them are willing to take drastic steps to improve. And if they’re not going to match that desperation, they might want to get out of the race entirely. Because if they don’t make a decision in one way or another, it won’t be too long until Joel Embiid makes the decision for them.