At the time she vanished in 1980, Karen Koppel was causing headaches for Ben Stein – a mob associate and felon whose Chicago janitorial company had grown fat through local government contracts.

Stein, who was in his 60s and married to someone else, wanted to break off what apparently was a romantic relationship with the much younger Koppel. However, Koppel wasn’t happy. She was making wild accusations about Stein, and demanded a large financial settlement to let things drop, Chicago police records indicate.

Stein asked a long-time friend – then-Chicago cop Richard “Rick” Simon, who moonlighted for Stein’s firm – to help amicably resolve things, according to police records and interviews.

Simon acknowledged to the Better Government Association meeting and talking with Koppel at a Rush Street-area tavern one crisp spring night 35 years ago. She left alone, and wasn’t heard from again, prompting missing persons investigations by the Cook County state’s attorney’s office and Chicago police.

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Simon – who took over Stein’s business interests after Stein’s 1996 death – was interviewed by police early on and has long denied knowing what happened to Koppel or doing anything wrong. Prosecutors convened a grand jury in the early 1980s to investigate Koppel’s disappearance, but Simon refused to testify, according to a police document obtained by the BGA.

Koppel has never turned up dead or alive, the case remains “open” and nobody has been formally cleared as a potential suspect, authorities said. Yet Simon has a noticeably different relationship with law enforcement these days: He not only socializes with Chicago Police Supt. Garry McCarthy, as previously reported by the Chicago Sun-Times. He also has donated to and possibly raised money for Cook County State’s Attorney Anita Alvarez’s political campaign, the BGA found.

All told, Simon and his business interests have given four contributions to Friends of Anita Alvarez totaling $5,000 since 2008, when Alvarez was first elected top prosecutor, according to Illinois State Board of Elections records. The most recent contribution came in 2011.

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More recently, a Richard Simon was also listed as a member of Alvarez’s campaign “finance committee,” a fundraising vehicle, but neither Alvarez’s office nor her campaign would say whether that’s the same man and, if so, explain his role and how he came to be part of the committee.

Frank Zera, a former prosecutor who handled the Koppel investigation in 1980 under one of Alvarez’s predecessors, then-State’s Attorney Bernard Carey, was told by the BGA of the donations and said, “I would be surprised that an elected prosecutor would take money from a person who was related to an investigation like that.”

 Garry McCarthy, Chicago Police Superintendent

The BGA also reached out to Carey, who is retired and living in Florida. He said in an interview that, while he does not know Alvarez or remember the Koppel case, as top prosecutor Alvarez should have known better than accept money from a potential witness or suspect – if for no other reason than the “appearance.”

For his part, Simon described himself as an Alvarez supporter. “If you want good effective law enforcement, you have to have good people in there,” Simon said.

Alvarez, facing a potentially tough reelection challenge next year, refused to comment.

McCarthy also refused to grant an interview, but police department spokesman Martin Maloney relayed via email, “The Superintendent has a personal friendship with Rick Simon which has no impact on the Chicago Police Department or its operations.”

Koppel still alive?

On the night Koppel was last seen, she met with Simon at Flapjaw’s tavern in Chicago, according to interviews, police records and news accounts.

Simon “had been conducting negotiations” with her “on Stein’s behalf” to end their relationship, according to an internal police report obtained by the BGA.

Some of Koppel’s associates suspected Koppel, who was in her mid-30s, ended up meeting with foul play, according to records and news reports.

Simon said in an interview he doesn’t know what happened to Koppel, but doesn’t buy that she was murdered.

Rather, he suspects she’s still alive with a new identity, having left Chicago because she was mentally unstable and horribly “humiliated” at being spurned by Stein.

Koppel’s family didn’t respond to interview requests from the BGA.

Simon describes himself as an upstanding citizen, a decorated former cop and a philanthropist. He has donated money to a number of other political figures, not just Alvarez. Simon’s business, United Service Cos., and its affiliates provide janitorial, staffing, security and other services for trade shows, corporate clients and others around the country.

Referring to the Koppel case, Simon said, “Are you writing a story or a history book? . . . You’re talking about an incident, what year? . . . Thirty-five years ago, and how many state’s attorneys have we had” since?

“It was investigated and I remained a member of the police department after that . . . and got promoted. . . . Give it a rest, please.”

Prompted by recent questions from a reporter, Simon said he “did a little checking” and found out the Koppel case is not being actively investigated by the state’s attorney’s office. He wouldn’t say who relayed this in Alvarez’s office.

Simon also said he was long ago “cleared” by police and prosecutors – an assertion that couldn’t be confirmed with the state’s attorney because Alvarez’s office wouldn’t answer a reporter’s questions. A Chicago police official, however, said that while the Koppel case is not being actively worked right now and there aren’t suspects, “it remains an open investigation so no one has been completely cleared at this time until we find out what happened with Ms. Koppel.”

In 1980, Carey convened a grand jury on the Koppel case, according to press accounts from back then. According to the internal police document, “Simon refused to testify before a Cook County Grand Jury investigating the disappearance of Miss Koppel.”

Simon gave a reporter differing answers on this subject in different interviews. At one point he said he couldn’t remember whether he had testified. In another interview he denied he had said this, and denied ever refusing to testify before a grand jury.

‘A likable guy’

With Koppel never turning up, the case presumably is still open at the state’s attorney’s office, even if it’s not active.

The BGA submitted a records request, under the Illinois Freedom of Information Act, or FOIA, to Alvarez’s office for records related to the Koppel case.

An Alvarez aide responded in a letter to the BGA that, “I have checked with the Criminal Prosecutions Bureau, the Felony Review division and our Cold Case unit and they have no documents that are responsive to your request. . . . I have not investigated whether any such grand jury records exist, as such documents – even if they did exist – would not be subject to FOIA.”

Koppel went missing the same year Carey was defeated by Richard M. Daley, the future mayor, in the state’s attorney’s race. It’s unclear how the case proceeded under Daley.

Daley did not return phone calls. But records show United Maintenance, a division of United Service, gave $1,500 to Daley’s main campaign fund in 2001 and another $1,500 in 2003. (Daley was mayor at the time.) Between 2009 and 2011, United Service donated $900 to the 11th Ward Democratic organization run by Daley’s brother, Cook County Commissioner John Daley, records show.

Alvarez’s immediate predecessor, Richard Devine, said he doesn’t recall the Koppel case resurrecting under his watch.

Simon said in an interview with a reporter that while he has donated to Alvarez, “I did no fund-raising . . . I did not solicit funds” for her. However, he indicated her campaign did solicit money from him.

Simon said he presumes it’s him listed on Alvarez’s finance committee in late 2013, but believes someone “put my name on the list” to gin up more donations. Simon said he knows a lot of people and “I’m actually a likable guy.”

Campaign officials for Alvarez said they aren’t sure whether the Richard Simon who runs United Service is the same person listed on Alvarez’s finance committee, or how the name got on the list.

Simon also has known people with reputed connections to organized crime, besides Stein. Simon has acknowledged he was in a side business for a few years with one alleged mob figure, William Daddano Jr.

Meanwhile, an FBI document from 1988 shows Simon was interviewed by two Chicago police officers who were assigned to the Joint Organized Crime Task Force and investigating the shotgun assassination attempt of reputed mobster Dominic Senese near his Oak Brook home. (Senese survived the shooting and died in 1992 of natural causes.)

Simon relayed “that he had known Dominic Senese and his family for so long that he could not remember how long,” according to the FBI document. As for the shooting, “Simon stated he had no direct knowledge.”

Simon told the BGA that any reputed mob figures he’s known were casual acquaintances and nothing more.

This story was written and reported by the Better Government Association’s Robert Herguth and Patrick Rehkamp. They can be reached at or (312) 821-9030.

Anita Alvarez image sourced via Facebook.

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