A controversial Justice Department official who’s caught the attention of the “Broadview Six” had contact with Chicago U.S. Attorney Andrew Boutros’ office and was involved in Operation Midway Blitz, sources told the Chicago Sun-Times.
It’s unclear what role Associate Deputy Attorney General Aakash Singh played in the Trump administration’s deportation campaign in the Chicago area last fall.
But defense attorneys for the “Broadview Six” are now seeking records that could tie Singh to that tainted case — if they exist. Charges were dropped last month against the Midway Blitz protesters following revelations of apparent prosecutorial misconduct.
The question about Singh’s involvement in the case comes after his name appeared prominently in a federal judge’s extremely rare decision in Tennessee last month to toss an indictment on selective or vindictive prosecution grounds. It came in the human smuggling case of Kilmar Abrego Garcia, who was charged criminally after successfully challenging his removal from the United States to El Salvador.
In his opinion, U.S. District Judge Waverly Crenshaw Jr. wrote that Singh pressured a top prosecutor, calling the case a “priority” and asking, “how close do we think we are to charging?”
Whistleblowers have also accused Singh of rushing the fraud indictment of the Southern Poverty Law Center in Alabama, according to Democrats on the U.S. House Judiciary Committee.
A source said Singh is friendly but known for pushing an extreme hard line — an approach reflected in other media reports. He once urged federal prosecutors to “go big and go loud” to generate headlines while charging protesters, according to The New York Times.
In January, he told high-ranking prosecutors from across the country that President Donald Trump was their “chief client,” Bloomberg Law reported. A co-worker also referred to Singh as an octopus with 93 tentacles — one for each U.S. attorney’s office he’s communicating with, according to the Bloomberg report.
So it’s not surprising Singh would be in contact with Boutros’ office. That’s especially true during Midway Blitz, which Boutros has described as the largest law enforcement surge in the history of the Chicago region.
Boutros’s office declined to comment. A Justice Department spokesperson said Singh “oversees the 93 [U.S. attorney’s offices] for the Office of the Deputy Attorney General, a position that exists across any administration.
“This necessarily entails the advancement of federal law enforcement priorities set by the president, the [attorney general] and the [deputy attorney general],” the spokesperson said. “While [the office of the deputy attorney general] articulates and advances these priorities, career [federal prosecutors] at each [U.S. attorney’s office] work with federal agents to investigate and prosecute individual cases, consistent with the law.”
Acting Attorney General Todd Blanche served as deputy attorney general until earlier this year, after Trump fired former Attorney General Pam Bondi and Blanche stepped into her old job temporarily. Trump has said he will nominate Blanche to serve as the nation’s top law enforcement official on a permanent basis.
The “Broadview Six” case revolved around a September protest outside a suburban immigration facility, where a crowd pushed, scratched and otherwise damaged a federal agent’s SUV. From that crowd, prosecutors charged only six people, all largely involved in local Democratic politics, raising questions about selective prosecution and freedom of expression.
Charged were former congressional candidate Kat Abughazaleh, Oak Park village trustee Brian Straw, former Cook County Board candidate Catherine “Cat” Sharp, 45th Ward Democratic Committeeperson Michael Rabbitt, musician Joselyn Walsh and onetime Abughazaleh campaign worker Andre Martin.
Boutros permanently dismissed charges in the case after U.S. District Judge April Perry revealed apparent misconduct by prosecutors during grand jury proceedings. She said the conduct was redacted from transcripts that had been given to her by the feds.
Those transcripts could be made public as soon as Monday.
The former defendants are now seeking attorneys’ fees, and they’ve asked for records of any communication between Singh and Boutros’ office related to their case. That includes “cell phone records from any cell phone used for such communication with Mr. Singh,” defense attorneys wrote in a recent filing.
The request is “well-supported based upon publicly available information regarding Mr. Singh’s direct involvement in matters of this type,” they added.
Boutros’ office previously said no communications exist with “anyone” outside his office, aside from local FBI investigators, regarding investigatory or charging decisions. They’ve said that includes anyone in the White House “and all components and offices of Main Justice,” referring to the Justice Department headquarters.
Perry once took prosecutors at their word on that. But that was before the judge discovered improprieties in the case. She told prosecutors “trust has been broken,” and the idea of vindictive prosecution “rears its head.”
A source who had contact with Singh outside of Chicago said Singh was in regular touch with the nation’s U.S. attorney’s offices. While friendly, Singh has also pushed the Trump administration’s extreme hard-line policies, the source said.
A law enforcement official confirmed Singh’s involvement in Midway Blitz operations in Boutros’ office.
A third source, who is familiar with Boutros’ office, said Singh was a point of contact on administration policy and its impact on Chicago cases in the months after Boutros’ April 2025 appointment. That was typical for someone in Singh’s role, the source said.
That person also said Singh, a former rank-and-file prosecutor, seemed to be “mindful of prosecutors and how prosecutors think about cases.
“They don’t think about them like politicians.”