In her first year on senior status for the U.S. Court of Appeals for the Seventh Circuit, Judge Diane Sykes is reflecting on the lessons she’s learned through her experience in the court system, beginning as a civil litigator, then as a Milwaukee County Circuit Court judge, and as a state and federal appellate judge, including service as a Wisconsin Supreme Court justice.
Nearly eight months after stepping down as chief judge of the Seventh Circuit and assuming senior status, Judge Sykes now lives along the Chesapeake Bay, close to family. It’s a different scene from her longtime home in suburban Milwaukee.
Senior status means Sykes is in “semi-retirement.” She still has a caseload and attends oral arguments in Chicago.
“I’m very grateful to have the opportunity to continue to be of service to the Seventh Circuit and to the people of Wisconsin and Illinois and Indiana,” said Sykes, who began her career as a reporter at the Milwaukee Journal Sentinel before attending Marquette University Law School, graduating in 1984 during the Ronald Reagan presidency.
A Civil Litigator on the Criminal Bench
Sykes arrived in 1992 at the Milwaukee County Circuit Court in the criminal rotation, starting with misdemeanors but spending most of her years judging felonies.
“That time on the criminal rotation was a formative experience for me,” Sykes remembers, “because I had been a civil litigator in my private practice and did not have criminal law experience. I needed to learn criminal law and trial processes very quickly” because “civil litigators don’t try a lot of cases.”
Sykes, who worked at Whyte & Hirschboeck, S.C. (now Husch Blackwell LLP) in Milwaukee, explained that a civil litigator “develops cases and works on pleadings and motion practice and discovery,” building theories for claims or defenses. The criminal docket in the Milwaukee County Circuit Court is very different. Amid “heavy caseloads” and “a very active calendar” in the state’s largest jurisdiction, she learned on the job. Her colleagues became mentors.
200 Trials
Her criminal rotation included two years in violent crimes court, which exclusively handles “homicide cases and sexual assault cases, including child sexual assault cases.”
Jay D. Jerde, Mitchell Hamline 2006, is a legal writer for the State Bar of Wisconsin, Madison. He can be reached by email or by phone at (608) 250-6126.
In her last year as circuit court judge, she was assigned to the civil division hearing large-claim civil cases. During her seven years on the Milwaukee trial bench, Sykes presided over “roughly 200 jury trials,” which she said gave her “a great perspective on the jury system.”
“It gave me a real appreciation for our jury system and the seriousness that most citizens who come to jury duty approach that responsibility,” Sykes said, adding that the system works well “for finding the truth and arriving at a just verdict.”
Across both the criminal and civil rotations, she learned firsthand that “juries make sensible decisions” and “make credibility judgments very well.”
She also found the building blocks of those decisions — charging decisions and the skill of trial lawyers and trial judges — exceptional.
On Discretion and Deference
When Justice Donald W. Steinmetz announced his retirement in 1999, Sykes saw an opportunity at the Wisconsin Supreme Court.
She worked her way through the governor’s appointment process, submitting a detailed application and participating in a series of committee interviews that culminated in an interview with Gov. Tommy G. Thompson, who appointed her in 1999. In 2000, Sykes was elected to a 10-year term. Her trial court experience served her well.
Trial court judges use their discretion to make many decisions, such as criminal sentencing and evidentiary rulings. “As a trial judge, I learned how weighty those judgments can be, which was great preparation for my work as an appellate judge,” Sykes said. “It also gave me a significant level of appreciation for the decisions that state trial judges make every day.”
She brings “a great deal of appreciation for and understanding of the deference that is owed to trial judges” to her appellate work. “I take seriously the trial judge’s superior position to make those judgments — every appellate judge does — but I have firsthand familiarity with having made those decisions.”
Wisconsin’s Most Cited
Sykes wrote the opinion in State ex rel. Kalal v. Circuit Court for Dane County, 2004 WI 58, the most cited Wisconsin case.
Westlaw confirms that Kalal has been cited in 1,636 opinions, as of this writing.
Kalal solved a chronic problem in state jurisprudence: inconsistent statutory interpretation.
“There was a push-pull from different panels of the intermediate court of appeals, and from different justices on the state supreme court as to the general methodology,” Sykes remembers.
Kalal offered an opportunity to clarify the appropriate method for statutory interpretation, she explained. The result provided “a framework for interpreting statutes” drawn from “general rules distilled from our case law” and “also from the textualist theory of statutory interpretation,” distinguishing between “the competing views of textualism and purposivism,” Sykes said.
Sykes couldn’t foresee how much of an effect the case would have, but she knows the issue is perennial. “Statutory interpretation will always be with us,” Sykes said. “We live in an age of statutes, and many cases involve questions of statutory interpretation.”
The opinion in Kalal could be considered a valedictory, one of her last written decisions on the Wisconsin Supreme Court.
A Bipartisan Path to the Federal Bench
On Nov. 14, 2003, President George W. Bush nominated Sykes as a Seventh Circuit judge, just over three years into her 10-year term on the state supreme court.
The appointment process began with Wisconsin’s unique bipartisan Federal Nominating Commission. The state’s two Democratic senators ensured that the commission would remain bipartisan by inviting Republican representatives, Sykes said.
The commission process required “a very comprehensive application,” much like the governor’s. It resulted in a list of candidates for President Bush to consider. Interviews followed with senators, the White House Counsel’s Office, and the U.S. Department of Justice.
With three states in the Seventh Circuit — Illinois, Indiana, and Wisconsin — national politics played a role. The U.S. Senate confirmed Sykes to the Seventh Circuit on June 24, 2004, by a vote of 70–27.
She started work on the court on July 1, 2004, using her trial court experience to review federal trial court decisions, with a twist. While Wisconsin circuit court judges often rule orally from the bench, federal district judges produce “many more written decisions.”
“I’m usually reviewing a written decision … that the judges had time to think about and research and assistance from support staff to prepare a reasoned written opinion,” Sykes explained.
But whether the decision is oral or written, “it’s the same principle of deference that’s owed to the trial judge’s decisions when it’s an issue that’s committed to the trial court’s discretion,” Sykes said. “So, my experience as a state trial judge has been very helpful to my reviewing authority as a Seventh Circuit judge, just as it was as a state appellate judge.”
Kalal’s Method, Erie’s Limits
The focus of Sykes’s interpretive work varies from state to federal court. Statutory and constitutional law are prevalent, and if they provide the rule of decision, an appellate answer becomes “interpretive work.”
Describing her process while on the Wisconsin Supreme Court, Sykes said she reviewed what the Wisconsin Court of Appeals had written on the subject to benefit from its analysis. From there, relevant decisions of other state supreme courts could be helpful.
Without anything from those sources, “it would be a true case of first impression.”
“We would proceed as we would with any other question,” Sykes explains. “If the case raised a constitutional question, we would look to the text and structure and history of the state constitutional provision in question. If it was a statutory case, we would look to the text and structure and context of the statute.”
“Federal judges are not common-law judges,” Sykes reminds us. “We take the common law as it comes to us from the state systems, and the state supreme court has the last say,” according to the Erie doctrine.
‘Of Service’
“As a senior status judge, I have a wonderful opportunity to continue to serve, but on a reduced basis,” Sykes said.
Sykes is easing in slowly as she settles into her new location. She’s working remotely with her staff when she isn’t needed in person in Chicago.
Sykes may eventually take up her interest in teaching, with plenty of law schools in the area to choose from, but that’s not the priority right now. “I really want to focus on my core work as a judge and be of service to the Seventh Circuit and the federal judiciary before I pick up any other kind of work.”
» Cite this article: 99 Wis. Law. 42-44 (October 2026).