Less than two weeks out from Media Day, the artificial deadline to complete offseason transactions is quickly treadmilling forward, putting an added layer of urgency on the Portland Trail Blazers in their saga with Damian Lillard.

Over the past few days, other teams have emerged as potential suitors for the All-NBA guard. It has been floated that the Bulls could be that “mystery team” linked to Lillard, and our pal Kyle Neubeck over at PHLY stoked the flames on their 76ers show.

On today's @PHLY_Sixers pod, we discussed the ongoing Lillard saga and a wild-card team I've heard is making calls to get in the mix — the Chicago Bulls

🎧https://t.co/4XneINe2SP pic.twitter.com/ereazkR6cB

— Kyle Neubeck (@KyleNeubeck) September 20, 2023

In theory, the Bulls could get into the Lillard sweepstakes using Zach LaVine or DeMar DeRozan. LaVine, the younger and more malleable player might fit better next to Lillard on paper. Maybe the Bulls can leverage DeRozan’s expiring contract into something more than LaVine’s remaining $185 million.

But the Bulls would need to send out $45 million to bring in Lillard and DeRozan’s $28 million would be too difficult to overcome without sending out Lonzo Ball’s money, attaching further assets to do so.

That leaves LaVine, who the Bulls may be forced to deal in part because he can net a greater return than DeRozan. But star-for-star swaps are not common in the NBA. Teams usually look to gobble up assets for a rebuild in preparation for a long rebuild. The Bulls have shown no interest in a teardown before, if they want to trade LaVine as the summer smoke may suggest, acquiring a star would be a great way to sell that to the fans while avoiding another long hibernation.

Financial impact

Before getting into whether or not this is a prudent basketball move, we must figure out whether it is financially possible.

Aside from whether the Blazers want LaVine, a swap doesn’t even work money-wise. If you were queasy about the LaVine max contract, boy does Lillard put that into perspective.

Not only is LaVine five years younger and signed through his prime years, he’s going to end up being $13.5 million cheaper in 2026-27.

But before we arrive at that future AK problem, they must solve for the $5.75 million difference between Lillard and LaVine’s money for this season.

A straight up swap would put the Bulls almost $7 million into the luxury tax. Of course, the trade likely wouldn’t be straight up — in order for the Bulls to pull off this kind of swing, they’d have to add another asset or three.

The Bulls however, they don’t have much in the way of realistic tradable contracts at the moment. Neither Coby White ($12.4M) nor Ayo Dosunmu ($6.4M) can be included —The CBA prevents players who were signed for more than 20 percent of their previous salary using Bird Rights until January 15. Jevon Carter ($6.2M) would close the gap, but recently signed players cannot be traded for three months after signing, preventing him from being moved until October 8.

All of this is to assume the Blazers have interest in LaVine, which by all indications is not a fair assumption to make. They are oriented around Scoot Henderson, Shaedon Sharpe and Anfernee Simons now, and while they have some veteran players on their roster including Jusuf Nurkic and freshly signed Jerami Grant, this Lillard saga has given them direction.

If the Blazers aren’t interested in LaVine, there would need to be a third party to whom LaVine would be directed. The Bulls could, in theory, send LaVine to a Mavs, a Hornets, a Pacers or some other team hoping to add a scoring weapon that improves their own title hopes. Then, the third party (along with the Bulls) would ship assets to the Blazers for LaVine.

Who knows if such a team exists.

Weighing the risk

Ultimately, it depends on the cost. Lillard has been adamant that he get traded to Miami and only Miami. The Bulls take on huge risk trading for a star has specifically asked to be somewhere else. With only one real suitor in the marketplace, if the Heat had offered anything the Blazers want, the deal would already be done.

So beating the Heat’s offer of Tyler Herro plus some future picks, salary filler and a young guy becomes the goal. But they’ll have to overtake the Heat’s offer without gutting the rest of their team. If they have to include Alex Caruso or Coby White or Patrick Williams, they may begin to neutralize any potential added championship equity the Bulls would gain from the delta in impact between Lillard and LaVine.

Let’s say the Bulls can flip LaVine to a third team, adding only one of their own future picks, the lottery protected pick they are owed by the Blazers and matching salary.

That kind of deal, if it is available, would significantly raise the Bulls ceiling. That fact can’t be stressed enough.

Buoyed by elite, high volume three-point shooting, foul drawing and basketball brilliance, Lillard put up a career-highs in points (32.2) on a career high in effective field goal percentage (56.4) while ranking in the 97th percentile in assist percentage. Lillard is an elite offense unto himself — the Blazers were +11.3 with Lillard on the court, ranking in the 99th percentile of the NBA.

He led the entire NBA in EPM, tied for second in the NBA in ESPN 538’s RAPTOR, 10th in Win Shares, Box Plus-Minus and VORP despite playing only 58 games and being a sub-average defender.

Lillard has already put together a Hall of Fame career that including two knockout playoff punches, a trip to the conference Finals, seven All-Star appearances, seven All-NBA teams and already on the NBA’s Top 75 players list.

In an Eastern Conference full of unknowns, Lillard’s star power markedly changes the Bulls outlook.

Without going into the tax or a drawn out rebuild, there are few options that could put the Bulls in a position to make the Conference Finals. Lillard would be one of the few, if any, conceivable ways to do that.

But it wouldn’t come without risk.

That doesn’t mean the fit would be seamless. LaVine is the more pliable compliment to another co-star, and while Lillard is a more dominant offensive talent than LaVine, his usage is much higher, his defense is much worse and his age-related decline is coming much sooner. It would be interesting to watch Lillard’s fit next to DeRozan and Vucevic unfold.

Still, getting even more win-now for a team that still likely wouldn’t be a title contender is bold, especially considering age. As much as it feels like the Bulls went all-in on their current roster, they left themselves with a few future draft picks and young players to be able to add down the line. It hasn’t made sense for the front office to pull the trigger on any other big swings, but this would truly be the last big move they could make.

A trade for Lillard would cap the team out more than they currently are. What if the deal would force the Bulls to empty the cupboard of young players and/or draft capital the Bulls hope to nourish and develop. It would age the core an additional five years, and while it may raise the group’s ceiling, it would give the team fewer outs to be able to recover and rebuild should the front office ever decide to do so.

The question comes down to opportunity costs and counterfactuals.

Perhaps there is a higher chance of success with Lillard than LaVine, but what win total or Playoff rounds would make the deal “worth it”? And what if things still don’t work out? Now you’re locked into an even older group with fewer future assets. Is that a better outcome than staying course?

At the same point, their current position is clear. If the continue course, what happens if they end up in the exact same position 365 days from now, having missed the playoffs and being forced to extend DeRozan because they can’t lose him for nothing?

Bringing Lillard to Chicago would make the Bulls better, at least more exciting in the form of different.

Aside from there not being a clear answer on any of these fronts, it seems exceedingly unlikely that the stars align to where the Bulls can actually pull this off. Until then, all points may be moot, but you have to applaud the front office for thinking big.