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Carol Felsenthal
On politics

Trump’s Leading Lady for the Supreme Court Has Chicago Ties

Diane Sykes, a judge on Chicago’s U.S. Court of Appeals, has decided cases regarding gun laws and First Amendment rights to film police officers.

Chicagoans couldn’t get one of their own—Judge Merrick Garland—on the Supreme Court last year. But this year, under Donald Trump, we could get another nominee with Chicago roots: Diane Sykes, a judge on the Chicago-based U.S. Court of Appeals for the Seventh Circuit.

President-elect Trump recently told reporters that he’ll announce his first high court pick “within about two weeks of Friday’s inauguration.”

Diane Sykes Photo: Wisconsin Court System

On nearly every short list I’ve seen, Diane Sykes, 59, ranks near the top. Yes, she’s a tad old compared to other candidates—see below—but she checks every other box that Trump promised.

During the GOP debate in February 2016, shortly after Justice Antonin Scalia’s death, Trump named Sykes and William Pryor, Jr., from the 11th Circuit in Atlanta, as two of the “fantastic people” he’d consider seriously for the court’s ninth seat. He did so even before releasing his first list of eleven names—Sykes and Pryor both on it—from which, he said, he’d choose.

Who is Diane Sykes?

Milwaukee-born, her law degree is from that city’s Marquette University, which would distinguish her from the glut of Harvard (four) and Yale (three) grads currently on the court. (Ruth Bader Ginsburg spent two years at Harvard Law, transferring her third year to Columbia, which granted the degree.)

Sykes’s undergraduate degree is in journalism, from Northwestern. In the year between graduating in 1980 and starting law school, she worked as a reporter for the Milwaukee Journal.

After clerking for a federal district court judge, she spent seven years in private practice at a Milwaukee law firm before becoming a Milwaukee County Circuit Court judge, handling both civil and criminal matters. Next, in 1999, came an appointment by then-Republican governor Tommy Thompson to the Wisconsin Supreme Court. She was elected to a 10-year term in 2000.

George W. Bush nominated her to the federal bench in 2003 and she was confirmed by the U.S. Senate in 2004 by the wide margin of 70 to 27. She had the backing of Wisconsin’s two democratic senators, Russ Feingold and Herb Kohl. Illinois’s Dick Durbin was a no vote, blasting Sykes for refusing to answer his questions on her views on abortion and Miranda rights. He called her, among other things, biased against defendants.

She was on Bush’s short list in 2005 for the Supreme Court following the resignation of Sandra Day O’Connor.

Trump has called his promise to nominate an unbending conservative the most important promise of the campaign. He has attributed his win last November to his focus on the court—telling voters that even if they don’t like him, “You have no choice. You got to go for Trump.” At a campaign rally, Trump warned that were Hillary Clinton elected, “You will have a Supreme Court that will destroy our nation.”

While Trump promises an Antonin Scalia clone, Senate minority leader Chuck Schumer promises a confirmation battle from hell if Trump follows through. (Extremely hard feelings among Democrats persist in the wake of the Republicans’ refusal to grant Obama’s nominee, Merrick Garland, a hearing.)

Sykes is often described as “a moderate conservative” as opposed to the aforementioned Pryor, who, like Scalia, is an originalist. Pryor has called Roe v. Wade the “worst abomination in the history of constitutional law.” He has described Roe as “a constitutional right to murder an unborn child.” Pryor has also said that same-sex marriage is not a right under the Constitution and that laws regulating it should be left to the states.

While the Los Angeles Times’s David Savage describes Sykes as having “ruled in favor of religious employers who challenged President Obama’s healthcare law and its requirement to provide free contraceptives, and she voted to uphold Wisconsin’s voter ID law,” shortly before the 2014 midterms, she has not “taken sharply ideological stands or called for overturning liberal precedents.” In 1993 she sentenced protesters who had blocked the door to an abortion clinic, telling them that they had “fine character” but their actions were illegal.

She wrote a majority opinion in the case of ACLU of Illinois v. Alvarez that advanced a citizen’s First Amendment right to record encounters with police while engaged in official duties in public places. The Illinois Supreme Court, quoting from Sykes’s opinion, later struck down the state’s eavesdropping statue that made such taping a felony offense if the person doing the taping did not have the permission of the person being taped. The court thus handed a major defeat to former state’s attorney Anita Alvarez, who lost reelection in the wake of the release of a videotape of the Laquan McDonald shooting.

On the other hand, Sykes does meet Trump’s campaign promises to protect the Second Amendment. She struck down a law that bans firing ranges within Chicago’s city limits.

One legal blog described Sykes as “a respected figure on the legal right and a favorite among the Federalist Society’s rank and file.” The Federalist Society and the Heritage Foundation helped Trump compile his list.

As the campaign wore on, that list eventually numbered 21. Anyone who has watched Trump knows he doesn’t always adhere to promises and that his pick could end up being someone who is not on any list and who is far more flexible than Scalia.

If Judge Sykes doesn’t get the nod this time, Trump might get a couple more cracks at the high court. Ruth Bader Ginsburg is 83, Stephen Breyer is 78, and swing vote Anthony Kennedy is 80. Trump has boasted that he would probably get more Supreme Court picks in one term than any president in history

Some analysts have Trump holding Sykes back until his second appointment, should he get one; the reasoning being that the first appointment can be unwaveringly conservative because extreme conservative Scalia could be replaced by another extreme conservative without changing the court’s balance. If Trump has a male candidate he really wants, for example, the aforementioned Pryor, who is close to Trump’s Attorney General nominee fellow Alabaman Jeff Sessions, now’s the time.

Next time, a reasonable conservative, and a woman such as Sykes —especially if Ginsburg is the justice being replaced—might be just what’s needed to pass muster with enough Democrats to win confirmation.

Sykes has an ally in fellow Wisconsinite Reince Priebus, Republican National Committee chief and soon to be Trump’s chief of staff. For Trump, the fact that Sykes was born, reared, and spent most of her career in Wisconsin is a plus. Wisconsin, after all, voted for Trump in the general election and helped give him his electoral college victory.

And those Midwestern roots and her law degree from a Catholic university might make her difficult to “Bork.” (Robert Bork, a Reagan nominee, lost an ugly Senate confirmation battle.)

If things get really testy, Republicans have the votes to abolish the filibuster which, under current rules, would require 60 votes to cut off debate. Were Republicans to implement the so-called “nuclear option,” they could confirm Trump’s pick with just 51 votes, and, in the process, score another payback against Democrats who, in 2013, then in control of the Senate, changed the rules to stop Republican filibusters of Obama’s lower court judicial nominees. That rules change specifically exempted Supreme Court nominees.

The biggest drawback for Sykes is her age; at 59 she’s older than the average age (53) on Trump’s list. (Merrick Garland was considered old at 64; Ruth Ginsburg was 60, considered on the old side, when she took her seat on the court.)

If Sykes’s last name sounds familiar, it might be because she’s the ex-wife of Milwaukee’s conservative radio talk show host, Charlie Sykes; emphasis on “ex.” Sykes, who recently accepted a new gig as cohost of a NPR show that will analyze Trump’s first 100 days, backed Sen. Ted Cruz in the GOP nomination melee. Charlie Sykes was also a leader in the “Never Trump” movement. A few days before the Wisconsin primary, Trump was expecting a puff-ball interview when he called into Sykes’s radio show only to endure a verbal beating. “Did you know that I’m a ‘Never Trump’ guy?” Sykes asked Trump. Their exchange went downhill from there as Sykes, in effect, called Trump “a 12-year-old bully on the playground.”

Sykes continued to whip up voters against Trump, who lost the Wisconsin primary to Cruz.

Were Charlie and Diane Sykes still married (they divorced in 1999) that, I think, would have been a deal breaker for the notoriously thin-skinned mogul turned president. Last May, Charlie tweeted, “Diane would be an outstanding choice. Would make a great justice. But I simply don’t believe Trump.”

With just days to go before Trump is inaugurated, his interviews with potential justices will likely happen in the guarded confines of the White House. Too bad for court watchers and reporters who will miss the chance to hang out in the lobby of Manhattan’s Trump Tower and get the scoop on which jurist is ascending the golden elevator.

I plan to keep an eye on Trump’s Twitter account. It wouldn’t surprise me if he makes this hugely consequential announcement in 140 characters.

David Lat, editor of legal industry website Above The Law, obviously embarrassed to be handicapping Supreme Court nominees by their looks, writes, “Trump is not your ordinary president. And as we know from his catty comments about people’s looks while on the campaign trail, as well as his willingness to consider Mitt Romney for secretary of state because he `looked the part,’ the Donald places a priority on appearance.” Lat rated Pryor as looking “like he could be a male model,” and that Sykes, “was named [in 2004] a Superhottie of the Federal Judiciary, described in her nomination blurb as `startlingly pretty and elegant.’”

That might just be the little extra something that Trump needs in making his choice.

Carol Felsenthal is a lifelong Chicagoan and self-proclaimed political junkie. She writes occasionally for Politico Magazine and The Hill. Her books include biographies of Bill Clinton, Katharine Graham, and Alice Roosevelt Longworth. Among her many stories for Chicago are memorable profiles of Michelle Obama and Bruce Rauner. Follow her on Twitter at @csfelsenthal.

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