Trump’s Chicago Crackdown Tests Loyalty of US Attorney Boutros

President Donald Trump’s Chicago crackdown is forcing one of his more conventional US attorneys, Andrew Boutros, to balance the district’s entrenched apolitical traditions against escalating White House pressure.

Boutros, a former career line prosecutor and Big Law white-collar leader, doesn’t at first glance fit the mold of outspokenly MAGA-aligned US attorneys who executed Trump’s prior law enforcement takeovers in Democratic-led Los Angeles and Washington.

His profile is sure to rise amid the administration’s attempted troop deployments and Trump’s call to jail the Illinois governor and Chicago’s mayor. Interviews with more than a dozen attorneys who know Boutros personally, used to work at the Chicago US attorney’s office, or are otherwise familiar with its current dynamics show deep division over how he’d respond to a directive from Washington to violate a court order, charge a Trump foe, or advance a weak case.

“The dilemma that US Attorney Boutros has is, where does his loyalty lie?” said Anthony Ghiotto, a law professor at the University of Illinois. “What I would anticipate is he’s going to try to placate the administration as much as he can without crossing the line.”

The possibility Boutros, 47, might be forced to cave or get replaced by a less-qualified loyalist isn’t theoretical. Trump last month insisted on the ouster of a Virginia US attorney who resisted his demand to prosecute two key enemies, before appointing a closer ally.

The indictment of former FBI Director James Comey “is a disgrace to the Department of Justice,” said Dan Webb, Chicago’s Ronald Reagan-era US attorney.

“Based on how I’ve seen him function,” Webb said of Boutros, “I would not believe that he would let that happen to the Chicago US attorney’s office.”

In a statement, Boutros said, “Rather than speculate as to what the Chicago US Attorney’s Office might or might not do under my leadership, I am on public record multiple times, including in television and print interviews, stressing that the Northern District of Illinois is a law-and-order district.”

“Every Administration is entitled to—and does—set Department of Justice policies and priorities,” Boutros added. “We are upholding these policies and priorities to the best of our abilities and in the proudest traditions of the Chicago U.S. Attorney’s Office.”

‘Not a Politician’

Boutros, a Republican, has sought to embrace the institutional norms of independence established by former US attorneys in Chicago appointed by presidents of both parties.

Shortly after he was appointed in April as the interim US attorney, Boutros was asked at a media roundtable if he agreed with the president’s then-US attorney in DC, Ed Martin, who described federal prosecutors as Trump’s lawyers.

“I’m the United States Attorney for the Northern District of Illinois. I’m not a politician, OK? I don’t need to speak for anyone else,” he said. “I’m the federal prosecutor here, the US Attorney for Chicago, and that’s my area of focus.”

The Chicago office has a long history cultivating political neutrality, a necessity during decades of combating the area’s pervasive public corruption. Two presidentially nominated Chicago US attorneys this century have spanned both Republican and Democratic administrations—a rarity nationwide.

Boutros is a friend of fellow University of Chicago law school lecturer Virginia Kendall, who is also Chicago’s chief federal trial court judge, two people familiar with the relationship said.

Kendall, who issued a statement Oct. 9 saying troops deployed by Trump weren’t needed at the courthouse, signed an order in July that made Boutros’ appointment permanent.

That judicial imprimatur—which reflects the agreement of the district’s trial court judges—contrasts him from counterparts in LA, Nevada, New Jersey, and elsewhere, where judges declined to approve temporary US attorneys.

Looser Standards

A handful of former colleagues said they’re impressed with his no-nonsense commitment to improving lackluster indictment statistics even while down about 40 to 50 prosecutors.

Still, multiple other Chicago attorneys said they were concerned by the departure of certain high-ranking prosecutors and a recent cluster of failed charges against Immigration and Customs Enforcement protesters. At least six of those lawyers said they fear Boutros will fall in line with the administration.

Trump wouldn’t install a US attorney whose loyalty he doubted and Boutros is considered very ambitious, his detractors said.

Some recent charges against protesters reflect newly loosened evidentiary standards in pursuit of White House-aligned criminal indictments, said several defense attorneys, who spoke on condition of anonymity to avoid reprisal.

Prosecutors’ track record in court so far is mixed: Of five people charged with assaulting or impeding federal officers after a Sept. 27 protest at an ICE facility, prosecutors have dismissed charges against all but one. The remaining defendant, a 70-year-old Air Force veteran, had his case downgraded from felony to misdemeanor.

In an extraordinarily rare move, grand jurors declined to indict two of the Sept. 27 protesters. When a federal judge later blocked the administration’s deployment of National Guard troops to Illinois, she cited that grand jury denial in her conclusion that the administration lacked credibility.

Son of Immigrants

Boutros, the son of Egyptian immigrants, was a federal prosecutor in Chicago from 2008 to 2015 pursuing complicated financial crimes cases. He’s particularly well-known for his case against a Silk Road drug trafficker who took in millions of dollars of Bitcoin.

The University of Virginia School of Law graduate went on to hold white-collar practice leadership roles at three firms, most recently Shook, Hardy & Bacon.

When Boutros was first chosen as US attorney, Ted Poulos said he was happy the job was going to someone trained in the office’s nonpartisan principles.

Poulos, a longtime criminal defense lawyer in Chicago and former federal prosecutor, acknowledges the duress this political climate might place on Boutros and his team.

That potentially entails juggling a desire to quit against the fear of what would happen to the office next.

“That’s all part of a difficult dilemma,” Poulos said, “that someone like Andrew may face.”