A businessman who has had ties to reputed mob figures and was once investigated in a still-unsolved missing persons case recently donated $1,000 to the campaign fund of Cook County State’s Attorney Alvarez – and it’s not the first time her campaign has taken money from him.

The Better Government Association reported in June that Richard “Rick” Simon and his business interests had given $5,000 to Alvarez’s campaign since 2008, when she was first elected top prosecutor.

The BGA also reported at the time there was a Richard Simon listed on Alvarez’s campaign finance committee – a major fundraising vehicle – though Alvarez refused to say whether it was the same man.

Now, campaign finance reports filed with the Illinois State Board of Elections show that Simon, who runs United Service Cos., donated another $1,000 to Alvarez’s campaign in a contribution dated Jan. 29 of this year.

Related Article: Alvarez Donor Was Once Investigated In Missing Person Case

Neither Alvarez nor her staff would answer questions about the money, including whether Simon’s campaign donations represent a conflict of interest for Alvarez.

Richard Simon donationSimon, a former Chicago cop, said via email, “as a former member of law enforcement in the community I believe my donation speaks for itself.”

A spokeswoman for Simon’s company would not say whether Alvarez’s camp solicited the donation but said, “He is still a supporter, he is not fundraising for her and he has not attended any of her fundraisers.”

Simon was questioned by police after the 1980 disappearance of Karen Koppel, who had been romantically linked to Simon’s friend and boss, now-deceased mob associate Ben Stein. The Cook County state’s attorney’s office was overseeing the case and at one time convened a grand jury – which Simon refused to testify in front of, according to a Chicago police document obtained by the BGA.

Koppel’s case remains unsolved and, while the investigation is not active, it’s still open with Chicago police and, presumably, Cook County prosecutors as well.

A retired prosecutor who handled the long-ago Koppel investigation under one of Alvarez’s predecessors was quoted in the BGA’s June story as saying, “I would be surprised that an elected prosecutor would take money from a person who was related to an investigation like that.”

Besides the Koppel case, Simon has acknowledged knowing people with reputed ties to organized crime, in addition to Stein.

Simon was in a side business for several years with alleged mob figure William Daddano Jr.

Simon also knew reputed mobster Dominic Senese and was interviewed by members of the Joint Organized Crime Task Force after somebody tried to kill Senese in 1988 near his Oak Brook home. Senese survived the incident and died several years later of natural causes.

In previous interviews, Simon portrayed himself as an upstanding person who is involved in a lot of charitable causes and knows a lot of people, but is not and never has been involved in the mob, had nothing to do with Koppel’s disappearance and knows nothing about who tried to whack Senese.

Simon also made news last year when the BGA revealed that Simon’s company, which provides janitors to businesses among other services, had been doing work for Rivers Casino in Des Plaines, a disclosure that raised concerns by Illinois gaming regulators.