The Seventh Circuit heard arguments on September 17th in Freehan v. Berg, the challenge to Illinois’s wine retailer shipping law. Illinois lets in-state retailers ship wine to Illinois residents but denies that privilege to out-of-state retailers.

The most important dynamic in the case may be a trap Judge Easterbrook set for himself. In Chicago Wine Co. v. Braun, he upheld Indiana’s comparable law because he found it was not discriminatory. But his opinion went further: if a law does discriminate, he reasoned, precedent requires striking it down, and the state doesn’t get to rescue it with evidence. “After Tennessee Wine a trans-border delivery rule that discriminates against interstate commerce is forbidden.” Chicago Wine Co. v. Braun, 148 F.4th 530, 534 (C.A.7 (Ind.), 2025). If the other two judges on this panel find that Illinois discriminates, Easterbrook’s own framework could point towards invalidating the law.

A Panel of Opposites

The panel brings together judges who have already landed on opposite sides of this question.

Judge Rovner sat on the panel in Lebamoff v. Rauner, which unanimously held that Illinois’s retailer shipping law was discriminatory, found it unjustified on the existing record, and remanded for the state to produce evidence supporting the discrimination.

Judge Easterbrook sat on the panel in Chicago Wine, which upheld Indiana’s retailer shipping law in a per curiam decision. The two judges in the majority agreed on the result but not on the reasoning, and each wrote separately. Easterbrook concluded the law did not discriminate at all. Judge Scudder assumed discrimination but found that Indiana had justified it.

That split matters. Because no single rationale commanded a majority in Chicago Wine, its precedential force arguably extends only to its result, not to either judge’s reasoning. That is a significant limitation when the Seventh Circuit already has a decision, Lebamoff, addressing the very Illinois statute at issue.

The third member of the panel, Judge Rebecca Taibleson, was the most active questioner and, I believe, the vote that will decide the case.

The Arguments

Alex Tanford, arguing for Freehan, contended that Lebamoff controls: it addressed this Illinois law, and the law has not changed since.

Judge Easterbrook disagreed, asserting that Chicago Wine had already determined how Lebamoff should be treated. Neither of the other judges weighed in on whether Chicago Wine displaced Lebamoff, or on whether a precedent addressing this specific Illinois statute still stands.

Judge Taibleson asked Tanford how the Indiana law differed from Illinois’. Tanford answered that Indiana’s law concerns retail delivery, while Illinois’s concerns retail shipping. She then pressed him on a practical question: how could Illinois possibly inspect out-of-state retailers? Tanford replied that the state could do what it already does with out-of-state wineries, which is license and permit them to make the system work.

Assistant Attorney General Sam Horan, arguing for Illinois, maintained that the law is not discriminatory because nothing prevents an out-of-state retailer from opening an Illinois location. He argued that Freehan therefore failed the first step of the Tennessee Wine framework.

That framework has two steps. First, the court asks whether the law discriminates against out-of-state interests. Second, if it does, the court asks whether the state has shown, with concrete evidence, that the law predominantly serves a legitimate interest such as public health or safety rather than protectionism.

Horan’s strategy seemed to be lock in Easterbrook’s vote on step one and bring Taibleson, who shares much of Easterbrook’s constitutional philosophy, along with him.

Why the Strategy May Fail

I think the gambit may have failed. Taibleson’s questioning was openly skeptical of the claim that Illinois’s law does not discriminate.

That creates a problem for the state. Taibleson seems unlikely to move to Easterbrook’s position on discrimination. The real question is whether Easterbrook can move to hers, and his own Chicago Wine opinion makes that difficult. If he accepts that the law discriminates, his framework says the law falls.

Taibleson’s questions on inspection and enforcement, however, suggest she is taking step two seriously. Where she comes down on the state’s evidence is the open question.

How the Opinion Could Come Out

There are several plausible outcomes.

The panel could find discrimination and hold that Illinois met its evidentiary burden, upholding the law. It could find discrimination and hold that Illinois failed to meet its burden, striking the law down. Or it could split: Taibleson might reject Easterbrook’s no-discrimination theory but join him in the result, finding the state’s evidence sufficient, much as Scudder did in Chicago Wine. That path would require Easterbrook to join a result on reasoning his own prior opinion rejected or be consistent and issue another opinion agreeing on result but disagreeing on process.

I expect Rovner would find it hard to rule for the state after joining Lebamoff. I expect Easterbrook would find it hard to abandon his no-discrimination theory from Chicago Wine. That leaves Taibleson. She is skeptical that the law is non-discriminatory; the question is whether Illinois proved its case.

My Prediction

Honestly, I don’t know. I was surprised when the Sixth Circuit ruled for the retailer in Block v. Canepa, and surprised again when the Eighth Circuit in Sarasota Wine Market grilled Missouri at oral argument and then ruled unanimously for the state. This area of law has a way of defying predictions.

I only hope this opinion doesn’t take the four years that Chicago Wine did.