Actor Jussie Smollett talks to the media before leaving Cook County Court after his charges were dropped, in Chicago. AP Photo: Paul Beaty, File

Longtime U.S. District Judge Ruben Castillo of the Northern District of Illinois was still settling into private practice late last year when he landed a high-profile client: the Cook County State's Attorney's Office, which is being investigated over the prosecution of former "Empire" actor Jussie Smollett.

The Akerman partner is one of a handful prominent lawyers who have been pulled into the messy legal saga, in which prosecutors dropped felony disorderly conduct charges against the actor after he allegedly paid two men to stage a hate crime attack against him and filed a false police report.

The State's Attorney's Office is being investigated by Dan Webb, the co-executive chairman of Winston & Strawn, who was appointed special prosecutor by a Cook County judge in August.

"Mr. Webb has a very broad mandate," Castillo said. "The State's Attorney's Office—you might be thinking, why does an office of lawyers need another lawyer—they're just like any other client. They understand the complexity of the situation they're in."

Webb has requested to review "every single type of communication that has occurred in an office of hundreds of attorneys," Castillo said. He and his team of five Akerman lawyers are reviewing Webb's requests to see if the documents he's requesting are privileged or not.

"It's a very exhaustive and thorough probe," Castillo said.

Meanwhile, Cook County State's Attorney Kim Foxx is being personally represented by Steptoe & Johnson senior counsel Michael Bromwich. Bromwich represented Christine Blasey Ford during Justice Brett Kavanaugh's Supreme Court nomination hearings, as well as former FBI deputy director Andrew McCabe.

Castillo said Akerman is not representing any of the Cook County State's Attorney's 700-plus lawyers on an individual basis. He said Foxx has instructed everyone to fully cooperate with Webb's investigation.

Castillo, who served on the federal bench in Chicago for 25 years, including a stint as the chief judge of the court, said Akerman has a commitment to representing local government agencies. When it began representing the Cook County State's Attorney's Office in October, Akerman discounted its hourly rates to between $250 and $375.

Bromwich, Castillo and Webb's respective careers have all converged at different points prior to this case. Both Bromwich and Webb prosecuted different Reagan administration officials involved in the Iran-Contra affair. And Webb was the one who hired Castillo as an assistant U.S. attorney in 1984.

Webb has not given a timeline for when he expects to complete his investigation. Foxx is up for reelection this year and is facing off against three Democratic opponents in the crucial March primary. Castillo noted the possibility that Webb could refile criminal charges against Smollett.

"He is not leaving any stone unturned. He has fully occupied my team for the last three months, in terms of trying to keep up on what he's doing," Castillo said.

The hiring of Castillo and Bromwich was first reported by Crain's Chicago Business.