The summer 2026 issue of the Marquette Lawyer magazine has a number of entries concerning the Hon. Diane S. Sykes, L’84, including a set of one-page essays by seven different faculty on how their Marquette Law School courses draw on her writings as a judge of the U.S. Court of Appeals for the Seventh Circuit since 2004 or as a justice of the Wisconsin Supreme Court between 1999 and 2004. This is the fourth of the seven essays. The illustration of the faculty member, taken from the magazine and appearing here with the blog post, is by John Jay Cabuay.
In Contracts, a required first-year course each fall, we use one opinion by Judge Diane Sykes. And this past year, a second of the judge’s opinions shaped my final exam.
The case we study together is Karma International, LLC v. Indianapolis Motor Speedway, LLC, a 2019 Seventh Circuit decision. The opening line draws us in: “The Indianapolis 500 race has been a fixture of American life since 1911, interrupted only by world war.” Judge Sykes wrote the opinion addressing mutual breach claims between an event-planning company (a licensee of Maxim, the men’s magazine) and the Indianapolis Motor Speedway over a disappointing party at the race’s historic 100th running.
We use the case to learn the requirement that contract damages cannot rest on speculation. The court of appeals affirmed summary judgment against Karma on its claim because its damages theory was “entirely speculative,” emphasizing that “a factfinder may not award damages on the mere basis of conjecture or speculation.” The facts make the principle memorable: although 1,787 guests attended Karma’s event, the company had sold only 92 full-price tickets. Most importantly, it could not provide concrete evidence how greater promotional efforts by the speedway would have caused more tickets to be sold or yielded more revenue. Students can grasp quickly why the law demands more than hopeful arithmetic.
The case also illustrates something I value in Judge Sykes’s work: her ability to show that older doctrines still have modern bite. Students read Chicago Coliseum Club v. Dempsey, an Illinois appellate decision from 1932, and can reasonably question whether the court was right to conclude that the promoter’s evidence on lost profits from a prizefight between Jack Dempsey and Harry Wills (which never happened) was too speculative. The doctrine can seem like a relic. Karma International demonstrates otherwise. The reasonable-certainty requirement remains very much alive, and Judge Sykes applies it with rigor to a modern set of facts.
My exam this past year drew from Quality Oil, Inc. v. Kelley Partners, Inc., a 2011 contract-interpretation case from the Seventh Circuit. Judge Sykes’s opinion rejected a literal reading of a handwritten provision in a loan-and-supply contract. The provision stated that the agreement would terminate after 225,000 gallons of motor oil and 225,000 filters were purchased, or 60 months, whichever came first. The buyer argued that this relieved it of all liability after 60 months, regardless of how much product it had actually purchased.
Judge Sykes acknowledged that the handwritten language was not facially ambiguous but explained that the plain-meaning presumption is rebuttable. The opinion draws on Judge Richard Posner’s earlier opinion for the Seventh Circuit, in Beanstalk Group, Inc. v. AM General Corp. (2002), which we also study in the course.
Two principles do the work. The first is the whole-contract rule—the precept that phrases in a contract cannot be read exclusive of other contractual provisions and that determining the parties’ intentions must involve reading the contract in its entirety. The second is the anti-absurdity principle, traced to Judge Benjamin Cardozo: “If literalness is sheer absurdity, we are to seek some other meaning whereby reason will be instilled and absurdity avoided.” Applying both principles, Judge Sykes concluded that the buyer’s interpretation was “commercially absurd” because it would allow the buyer to retain a $150,000 loan, let 60 months elapse without purchasing anything, and walk away free.
At a recent Marquette Law School event honoring Judge Sykes, her fellow Marquette lawyer and former clerk, Anne-Louise Mittal, L’15, observed that what stood out to her most was Judge Sykes’s ability “to cut through even the most complicated case to identify the governing legal principle or principles at the heart of the case.” That is precisely what these two opinions do. Karma International homes in on the principle that speculation is not proof. Quality Oil quickly arrives at the principle that text serves commercial purpose, not the other way around. Judge Sykes no doubt is a textualist, but Quality Oil shows she is not a blinkered one.
As we celebrate Judge Sykes upon her taking senior status on the Seventh Circuit and after serving as the court’s chief judge, my contribution to marking the occasion is simply to make this point: her opinions continue to teach.