Why you should care

Judge Diane Sykes is a Midwestern originalist who’s serious about the law, but seriously hard to predict.

For three decades, one man has held down the center of an often divided U.S. Supreme Court: Justice Anthony Kennedy. With rumors swirling that the current term may be Kennedy’s last on the bench, OZY is taking a look at what the court might look like in his absence and whom Donald Trump might nominate to take his place. This is Life After Kennedy.

One evening while folding laundry in her kitchen, Diane Sykes was half paying attention to the TV when Fox News host Bill O’Reilly caught her ear with a segment about a “deadbeat dad.” Sykes’ face suddenly hit the screen, along with those of two female colleagues from the Wisconsin Supreme Court and a sketchy-looking defendant, as O’Reilly intoned: “Why do these women want this man to have more children?” The “No Spin Zone” had stretched the facts a tad. Sykes and her colleagues had merely argued that a judge’s prohibition on David Oakley fathering more children as a condition for his probation overstepped the U.S. Constitution.

Telling this in her aw-shucks Midwestern manner to a chuckling crowd at Duke University’s law school in a 2010 speech, Sykes pointed out that O’Reilly’s dig wasn’t a problem for her liberal colleagues. But the conservative justice’s phone started ringing off the hook. “I know a lot of people who watch the Fox News Channel,” she said.

Now sitting on the 7th U.S. Circuit Court of Appeals, Sykes — an originalist who rejects the notion that the Constitution evolves — is an active member of the influential Federalist Society of conservative lawyers. She has popped up on President Donald Trump’s shortlist of candidates for the U.S. Supreme Court, meaning she’ll be in the mix if an opening arises in the coming months. But as the Fox News watcher-in-chief weighs his options, he has in Sykes someone who doesn’t fit the typical mold. She comes from the heartland, not the Ivy League, and has an unpredictable streak of siding with liberals at times, including on the most heated issue any SCOTUS nominee will face: abortion.

Her matter-of-fact interpretation of the law sometimes leads her against conservative orthodoxy.

Sykes was born and raised in Milwaukee. She attended Northwestern University for journalism and Marquette Law School. (All nine current members of the Supreme Court attended Harvard or Yale law, though Ruth Bader Ginsburg graduated from Columbia Law School.) Sykes worked as a reporter for the Milwaukee Journal Sentinel in the early ’80s but “always wanted a career in public service,” says her former husband, Charles Sykes, an MSNBC contributor who hosted a conservative radio show in Milwaukee for many years. Judge Sykes looked up to her father, who was an engineering consultant for the government, and dreamed of following in his footsteps, according to her ex-husband.

After law school, Sykes clerked for a federal district court judge, worked as a private practice lawyer and, in 1992, became a Milwaukee County Circuit Court judge. The then governor, Republican Tommy Thompson, appointed Sykes to the Wisconsin Supreme Court in 1999, and voters elected her to a 10-year term in 2000. George W. Bush nominated her to the 7th Circuit, and the Senate confirmed her, 70-27, in 2004. Support from across the aisle, including Wisconsin’s Democratic senators, pushed Sykes through at a time when Democrats mounted filibusters against several nominees they considered too right wing. “Her judicial philosophy is conservative, but she has a lot of integrity,” says Janine Geske, a Marquette law professor and former Wisconsin Supreme Court justice who has known Sykes for 25 years. “She’s very respected on both sides.”

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Sykes has racked up a conservative record, ruling against the Affordable Care Act’s contraceptive coverage mandate and overturning severe restrictions on private firing ranges within Chicago city limits as infringing on the Second Amendment.

But her matter-of-fact interpretation of the law sometimes leads her against conservative orthodoxy. In 2012, Sykes sided with Planned Parenthood, saying a federal Medicaid law trumped an Indiana law banning state and federal funds from going to organizations that provide abortions. As a Wisconsin trial judge, Sykes gave two activists a 60-day jail sentence — close to the maximum — for blocking the entrance of an abortion clinic in Milwaukee, though she made a point of telling the defendants she respected the “courage of your convictions.”

Those rulings have drawn fire from Andy Schlafly, an Eagle Forum lawyer and son of intrepid conservative activist Phyllis Schlafly. “Diane Sykes has a pro-choice record,” Schlafly said during a strategy call with his coalition in 2016. “I don’t know why she’s even on [Trump’s] list.”

And liberals are not exactly embracing her. Sen. Dick Durbin, D-Ill., voted against Sykes’ appeals court confirmation, objecting to her declaration of respect for the anti-abortion activists and saying she dodged his questions on her abortion views. And while she’s more circumspect than some conservative court hopefuls, she’s given the left plenty to criticize. Consider her dissent in last year’s Hively v. Ivy Tech Community College case. Sykes argued that sexual orientation should not be protected under Title VII of the Civil Rights Act of 1964, criticizing her colleagues for “upending” precedent and essentially creating law that contradicted the “constitutional structure.”

Her life is the law. Sykes prepares for oral arguments while climbing the elliptical machine, judges moot court competitions and attends law school conferences in her free time, she told the Wisconsin State Bar in a 2014 interview. Rare non-legally minded moments usually involve spending time with her two sons.

Even though Sykes, 60, is older than many of Trump’s potential picks and might not last as long on the court, her profile as a moderate-seeming woman could be a suitable fit to replace swing Justice Anthony Kennedy, now rumored to be mulling retirement. And Geske points to Sykes’ political constituency. “She’s friends with [House Speaker] Paul Ryan and [former White House chief of staff] Reince Priebus, and Governor [Scott] Walker thinks highly of her,” Geske says. “If Trump is listening to the people of Wisconsin, a state that voted for him, she could definitely still be nominated.”

Then, perhaps, the spin on an O’Reilly-free Fox will be kinder.

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