Red, white and green lights twinkled overhead as Chicago’s police chief stepped onto the Brooklyn street.
Supt. Matt Rodriguez beheld the last strains of the festival of San Cono, a daylong pageant of processions, prayers and food that honored a humble Italian saint.
At Rodriguez’s side was his worldly guide, the pal he treasured enough to call “a brother,” convicted felon Frank Milito.
A North Side businessman whose maladroit English hardly masked his flinty intelligence, Milito had invested with a Chicago mob boss and come under scrutiny during a high-profile homicide investigation. Yet he also held court at his Wells Street restaurant, filling the plates and glasses of his many friends in law enforcement.
Rodriguez would be forced to resign within weeks of that 1997 New York vacation when he acknowledged a friendship with Milito in a Tribune interview. But Milito’s financial and personal ties to Rodriguez were far more extensive than previously known, and Milito’s access reached beyond the superintendent to other ranking members of the Police Department.
Since the days of Prohibition, when crooked cops and gangsters bloodied Chicago’s neighborhoods and corrupted its courts, police Rule 47 has prohibited officers from fraternizing with criminals. The vast majority of Chicago police officers do their work and risk their lives with unheralded integrity. But Rule 47 has been openly defied and rarely, if ever, enforced.
Crime figures forged ties of money or friendship with certain Chicago police supervisors and officers during the last decade as key investigations drifted or were derailed, a Tribune investigation has found. Records and interviews show:
– Even when confronted with disturbing details of the relationship between Rodriguez and Milito, the FBI and U.S. attorney’s office reined in investigators for fear of alienating the Chicago Police Department.
– Milito’s relationships with police and county sheriff’s officers tainted the probe into the 1987 slaying of Amoco Oil Co. executive Charles Merriam, in which Milito fell under investigation. At least one witness was hesitant to cooperate because Milito was a friend of Chicago’s police chief, and some investigators privately questioned the integrity of the probe.
– As the investigation bogged down, Milito and a Chicago police officer invested with a high-ranking sheriff’s officer on the Caribbean island of Curacao, where they bought shares of a crime syndicate-linked hotel and casino.
The sordid relationships between police and criminals ranged from the top of the department to the rank and file:
– A cluttered Northwest Side tailor shop was a hangout for police and crime figures for more than two decades, according to internal police reports and interviews. Top police officials were seen there with a criminal during a 1994 internal police surveillance.
– A crime syndicate figure employed tactical officers for security at his adult bookstores. Those officers also were investigated for the million-dollar rip-off of a drug courier.
In a prepared statement, U.S. Atty. Scott Lassar said, “Police corruption has been and continues to be a high priority of this office.”
Thursday, Lassar’s office indicted retired Deputy Supt. William Hanhardt for allegedly leading a band of mob-linked thieves who robbed jewelers of $5 million between 1984 and 1996. The charges against Hanhardt, who had influence over personnel decisions and access to internal police information, hint at the all-too-common bonds between cops and criminals, records and interviews show.
Three years ago, just days before Milito’s vacation with Rodriguez, a Chicago police official handed Rodriguez a sheaf of internal police reports that showed Milito and two associates had come under investigation in two other killings besides Merriam’s.
Rodriguez studied the reports, which detailed the slayings of two mechanics amid a gritty world of gas station operators, crime syndicate enforcers and beat cops. One of three station owners–Milito, his brother-in-law or their friend Pierre Zonis–emerged as a witness or potential suspect in each slaying, then receded into the background of the next case, like figures on a spinning mobile.
Zonis, who befriended a mob enforcer and was questioned several times about the unsolved slayings, became a Chicago police officer in 1994.
Rodriguez would later tell federal agents that he was “deeply disturbed” by the reports.
But he apparently quelled his misgivings by the time of the San Cono festival. While in New York, he and Milito took their wives to see the Broadway musical “Titanic.”
Rodriguez sprung for the $375 tickets.
Friendship and favors
The relationship that would reverberate through the highest levels of law enforcement in Chicago began as two men of humble backgrounds pushed their way to the top.
Rodriguez was living on the North Side, near Milito’s Fullerton Avenue gas station, when a business executive introduced the up-and-coming sergeant to the immigrant entrepreneur.
The son of a Mexican-American grocer and precinct captain, Rodriguez was close to the immigrant experience himself. He had taken the streetcar every morning from the insular Back of the Yards neighborhood on the South Side to Holy Trinity High School on Division Street, where he graduated fifth in his class.
He studied just as hard for the police exams that vaulted him through the organized crime, gambling and youth divisions. A careful, solid administrator, he caught the eye of gambling unit Lt. Richard Brzeczek, who in 1973 made Rodriguez his supervising sergeant.
Before appointing Rodriguez, Brzeczek checked him out with federal authorities. “He sat good with the FBI in the 1970s,” Brzeczek said.
During his decade in the police Organized Crime Division, Rodriguez said, he got a firsthand glimpse of the ways criminals can corrupt police. Once, he recalled, after he and a partner spent days monitoring a North Pulaski Road mob gambling operation, the mob workers carted out their equipment about two hours before a scheduled police raid–apparently tipped off by a leak from within the department.
Rodriguez said he felt “totally deflated” about the leak, and guessed the officer responsible “is probably sitting in Florida right now, basking in the sun.”
As Rodriguez quietly worked his way up to the superintendent’s post, he brought his friend Milito to police headquarters and introduced him to those who controlled key personnel and law enforcement decisions, Brzeczek said.
After he immigrated to America in 1962 from Italy, Francesco Rocco Milito gave generously to Democratic politicians and built an eclectic portfolio of businesses that would include eight gas stations, two travel agencies and $1 million worth of North Side real estate. Milito declined to comment for this report, but offered some information through his attorney.
More Top Picks Best Smart Toilets With Auto Open
Among the businesses he oversaw was a plush Old Town restaurant, Orso’s, where police brass gathered to discuss department politics and to toast promotions. Milito showered favors on many of his law enforcement friends, but none more so than Rodriguez, internal U.S. Justice Department records and interviews show.
Using his travel agency, Milito arranged for them to vacation together in Italy, Israel, California, Arizona, New York, Colorado and the Bahamas. Milito never told Rodriguez how much the trips cost. Instead, Rodriguez attempted to reimburse Milito by providing out-of-pocket cash or paying for incidentals until Milito said they were even, records and interviews show.
Milito registered Rodriguez with the International Association of Travel Agents, a perquisite that brought Rodriguez travel discounts.
He hired Rodriguez’s son-in-law at his restaurant when the young man was between jobs, and he employed Rodriguez’s daughter at his Sunset Travel agency.
Milito donated $1,000 to a police “recognition party” held when Rodriguez was promoted to superintendent in 1992. Some $3,900 raised for that party eventually was transferred to Rodriguez’s personal bank account, records show. Such parties honoring the promotion of police commanders–at which lower-ranking officers and civilians make donations that allow them to mingle with those who control district assignments–are an established ritual in Chicago.
If Rodriguez needed to get away from the office in the afternoon, Milito let the chief use one of his North Side condos.
“It was a nice, quiet place to take your tie off and sit down,” Rodriguez said in a Tribune interview.
He could often do more paperwork at one of Milito’s apartments with a ballgame on than at police headquarters where subordinates wrangled for his attention, Rodriguez said.
“Every time I went there I went with my briefcase,” he added.
Throughout the 1990s, Milito’s family had a city contract to wash police cars, and city ethics laws bar officials from accepting gifts from those with an interest in city business. But Rodriguez said the favors extended to him by Milito were simply tokens of friendship.
“There was no quid pro quo,” Rodriguez said.
Rodriguez acknowledged that Milito once requested the transfer of a lieutenant with whom he had a close relationship.
Lt. Ned Dolcimascolo had managed one of Milito’s gas stations before he became a police officer, then worked again for Milito during a year’s leave of absence in 1982. Eight years later, Milito lent $10,000 to fund a salon run by Dolcimascolo’s wife, records show.
Dolcimascolo, who has been saluted numerous times for professionalism and bravery in the police Daily Bulletin, declined to be interviewed, although he provided some records about the loan through Milito’s attorney.
Rodriguez approved Dolcimascolo’s request to be transferred to a North Side police district, but said that he simply rubber-stamped paperwork that was already being processed. Through his attorney, Milito denied requesting Dolcimascolo’s transfer.
Rodriguez was only one of Milito’s high-profile police friends. Phone records gathered during a mid-1990s federal investigation of Milito showed calls placed from his phone to the private lines of top police officials including those in charge of the Vice Control Division, which oversaw liquor licenses at restaurants such as Orso’s.
Milito’s attorney, Paul Julian, said Milito was simply calling to talk to his many friends in the department.
Milito traveled with former Chief of Detectives John T. Stibich to Rome after Stibich was retired. Stibich declined to discuss his relationship with Milito.
One of the first officers with ties to Milito was Sgt. Arthur R. Smith, who had a heart attack and died in 1994 while trying to kill the ex-wife of a Las Vegas restaurant chain owner. Smith served as a reference when Milito became a U.S. citizen, naturalization papers show, and Smith later cited Milito as a reference when he rejoined the department after a leave of absence in 1976.
While he socialized with his police friends, Milito fell under the scrutiny of federal and local investigators and faced a new and more potent threat to his expanding business.
During a four-year period in the 1980s, Milito had failed to report the sale of $4.6 million worth of gas from four stations, federal prosecutors alleged. In 1986, Milito pleaded guilty to mail fraud and a tax charge and was sentenced to 9 months in prison.
Because of that conviction, Amoco District Manager Charles Merriam, a corporate go-getter who oversaw 825 Midwest gas stations, moved to revoke Milito’s leases. As Milito was forced to turn over gas stations to new owners, the two men confronted each other and Milito sued Amoco.
When Merriam was gunned down in his Prospect Heights home in November 1987, Milito came under investigation, although no charges were brought. No physical evidence links him to the slaying, and through his attorney he vehemently denied having any involvement in it.
The homicide investigation was overseen by a friend and golfing buddy of Rodriguez’s in the Cook County Sheriff’s Police Department.
The sheriff’s investigation was compromised by delays and missteps as the crime scene took weeks to process and sheriff’s department records and internal computer files were lost, the Tribune found. While no law enforcement agency suggested that Rodriguez interfered with the investigation, and he denies doing so, some investigators worried that Milito’s ties to Rodriguez had a chilling effect. At least one key witness expressed anxiety about helping investigators because of the friendship.
Another potential witness located by the Tribune said he would not cooperate with authorities because of the specter of corruption among law enforcement officials investigating the killing.
Early probes languish
Chicago police and federal authorities were aware of Rodriguez’s relationship with Milito, but the administrative mechanisms designed to protect the integrity of the police department seemed to falter.
Internal Affairs Division officials gathered evidence during a 1993 inquiry into Rodriguez’s use of vacation time that Rodriguez and Milito traveled together overseas, but former internal affairs officials said in interviews that they felt it was not their place to question the superintendent’s friendships.
The FBI questioned Rodriguez about his ties to Milito in 1993, but that interview was overseen by a supervisor who asked no probing questions, an FBI report and interviews show.
A former FBI supervisor involved in the inquiry said the FBI treated Rodriguez “diplomatically” because the Justice Department needed the cooperation of Rodriguez’s Police Department to build cases against drug dealers and street-gang members.
Three years later, in 1996, federal prosecutors asked then-U.S. Atty. James B. Burns to consider including Rodriguez and at least three other police officials in a grand jury probe of police corruption. Federal agents had gathered evidence of Rodriguez’s ties with Milito and questioned whether crime figures exerted influence over police personnel decisions.
Burns authorized his prosecutors to expand their grand jury investigation to include three police officials but not Rodriguez, a January 1997 federal memo titled “Ground rules for investigating Matt Rodriguez,” shows.
While prosecutors were allowed to make “generic” inquiries and to use means other than the grand jury to learn about Rodriguez, they were instructed not to subpoena Rodriguez’s personal bank accounts, his police personnel file or a hotel contract for the 1992 promotion dinner in his honor without approval from Burns. They were told not to use Rodriguez’s name on subpoenas without the express approval of Burns.
Burns, who stepped down as U.S. attorney in August 1997, declined to comment on details of the grand jury proceeding.
One law enforcement official who took part in the discussions about Rodriguez, and who spoke on the condition that he not be identified, said a supervisor in the U.S. attorney’s office questioned whether agents had gathered enough evidence to trigger an investigation of Rodriguez. In addition, the official said, Burns wasn’t willing to jeopardize “our cooperation and the two offices working together.”
The memo “doesn’t say their water is going to be shut off, it says, You’ve got to get approval,” the official said. “And to me, that’s just good judgment.”
It was not until February 1998, three months after Rodriguez had resigned, that federal agents visited the former police chief at his home and asked specific questions about the extent of his financial ties to Milito.
No charges have been brought as a result of the investigation.
Tailor shop regulars
Rodriguez wasn’t the only police official casually meeting with a criminal.
On a chilly Saturday morning in December 1994, an internal police investigator set up a hidden surveillance camera outside a cluttered tailor shop at 5257 N. Central Ave.
FBI and police Internal Affairs Division investigators had gathered unconfirmed statements from informants who said police met with bookmakers at Joseph’s Tailor Shop and leaked information to crime figures there.
At 9:40 that morning, a black, unmarked sedan slid into the shop’s back lot. Supt. Rodriguez left his driver in the car and stepped into the shop.
No criminals were in the shop at the time, so Rodriguez’s presence violated no department rule. But his appearance marked an unexpected twist in a probe that would roil the police Internal Affairs Division and raise questions about the department’s exposure to criminal influence that have not been answered to this day.
Rodriguez said he did not know he had come under internal police surveillance at the now-closed shop, and added that he never saw anything untoward happen there.
“I would have made the first report, initiated an investigation myself,” he said. “It was just a hangout for policemen … only there’s no booze. If it was more than that, I certainly don’t know.”
As they watched from outside the shop over three months in 1994, internal police investigators could only guess at the conversations that took place in a back room secluded by racks of suit jackets, where ceiling fans stirred the warm air.
The surveillance reports show that the parade of Saturday morning regulars ranged from then-Deputy Supt. George Ruckrich, the department’s third in command, to Charles V. Gentile, a former Chicago police sergeant who had been forced to resign in 1987 after he was convicted of using a false name, a misdemeanor, while being questioned by federal agents. U.S. Drug Enforcement Administration officials had stopped Gentile after he allegedly tried to pick up a cocaine-packed suitcase at O’Hare International Airport.
Police Internal Affairs Division reports list several crime figures known to hang out with police brass at the tailor shop over the years. Among them were insurance swindler Allen Dorfman, who was gunned down in a 1983 mob hit, and former Police Officer Anthony Chiavola, now deceased, who was convicted in the storied Chicago mob case that exposed crime syndicate skimming at the Tropicana casino in Las Vegas.
Gentile, who visited the shop in the 1990s, said it was no secret that crime figures frequented the shop. “We all knew that,” Gentile said in an interview. “They all were in there.”
But Gentile said the only conversations he heard were about baseball and women. “They would joke and talk, [like] guys standing on the corner when I was younger,” he said.
More Top Picks Best Lightweight Rain Pants
“The [police] higher ups used to go outside and converse with each other or have their own conversations, but I wasn’t privy to that. Who knows what they were talking about.”
Another tailor shop regular, former Detective Fred Pascente, said reputed bookmaker Matt Raimondi also frequented the shop during the 1990s.
“I was in there with him a number of times,” said Pascente, who resigned from the department in 1993 and later pleaded guilty to committing insurance fraud with a group of criminals.
Raimondi, a former city worker who has been described by federal prosecutors in court records as a violent mob enforcer and bookmaker, also pleaded guilty to insurance fraud with the same crime ring. He said in a Tribune interview that he was only at the shop to drop off tailoring or in his capacity as a driver for the late Ald. Anthony Laurino (39th), who visited regularly.
Also frequenting the shop during the 1990s was Donald Angelini, 64, a mob gambling overseer known as “the Wizard of Odds,” according to shop regular Officer John Matranza. Rodriguez also said he saw Angelini once in passing at Joseph’s. Angelini declined to comment.
Clearly, the shop was a comfort zone for the command ranks. Once, with several top police officials there, commanders brought tailor Joseph Rozenberg a birthday cake with an old-fashioned sewing machine drawn in chocolate on the white icing. Then they ushered in a stripper in a look-alike police uniform.
As a home video camera ran, she strutted to a boom box rendition of the disco hit “Nasty Girl.” While the immigrant tailor sat immobile, she placed her police cap on his frazzled hair and unbuttoned his plaid shirt.
The FBI put the tailor shop under surveillance briefly in the late summer of 1995, but no charges were brought. They even questioned Rozenberg, who died in 1997, according to Gentile.
But Rozenberg, who had escaped a Nazi labor camp in France and then survived the wartime black market by selling Germans tins of butter partially filled with sand, brushed off his federal interrogators by telling them he would give the agents a 10 percent discount, just like he gave all police officers, Gentile recalled.
Gentile added, “It is difficult for me to convey the charm or allure of the location.”
Days after Rodriguez walked into the tailor shop, the Internal Affairs Division surveillance was shut down.
Then-internal affairs chief Raymond Risley said in an interview that he cut short the investigation because he felt it would be ethically questionable for him to conduct a secret probe of the superintendent to whom he reported.
During a series of meetings in early 1995, Risley and the two subordinates in charge of the tailor shop investigation–then-Lt. Eugene Karczewski and Sgt. James Doody–sat down with federal prosecutors and agents to discuss the tailor shop surveillance reports and other evidence of organized crime influence in the Police Department.
The meetings were held in an office a block away from the FBI and U.S. attorney’s offices to minimize the chances that someone might spot Risley, Karczewski or Doody. The Internal Affairs Division investigative reports were removed from official police files and turned over to the U.S. attorney’s office.
Within months, those Internal Affairs Division officials were dispatched to other posts or ordered to focus on corruption among lower-ranking officers.
The team was “effectively neutralized,” one later federal report said.
In August 1995, Risley was promoted to the organized crime division, removing him from the investigation. He resigned from the department in 1999 and became police chief of suburban Country Club Hills.
Karczewski was transferred to a Far South Side district in November 1995. He resigned in January 1996 and became chief of police in suburban Riverside.
And Doody, who remains in the Internal Affairs Division, was ordered to concentrate on beat cops instead of higher ranking department officials, interviews show. Doody declined to comment for this report.
Rodriguez said in an interview that the personnel changes were made to strengthen the Internal Affairs Division and make it more effective at rooting out corruption. Rodriguez said he was concerned about reports of serious misconduct among patrolmen as opposed to higher-ranking officers.
“I thought there had to be a new tack,” he said.
An abrupt departure
In November 1997, Rodriguez publicly acknowledged his friendship with Milito in a Page 1 Tribune story. The next day, the soft-spoken commander stood before television klieg lights in a gold-braided police cap and resigned, abruptly ending a 38-year police career that should have been capped with praise for his oversight of Chicago’s community policing initiative and the city’s drop in crime.
The superintendent strolled off into a police afterlife of lecturing on law enforcement and playing golf at the Eagle Ridge Inn & Resort in Galena, leaving the secrets of his relationship with Milito buried in law enforcement files.
After he resigned, Rodriguez said, he cut off all ties with Milito, with whom he once talked on the phone almost every day. “If I didn’t feel troubled about it, the friendship would still be going on, and it’s not,” Rodriguez said.
But a pained ambivalence crept into his voice. He said he was uncomfortable even mentioning that their relationship was over because Milito’s feelings might be hurt if he saw that in print.
“This guy slept at the gas station, slept behind the counters, and really broke his butt to make the business he did,” Rodriguez said. “You have to have a lot of respect.”
Had it not been for their friendship, Rodriguez added, Milito might never have attracted attention.
“He is a page 42 guy, but you hook it up with the superintendent and all of a sudden it’s on Page 1,” Rodriguez said. “I felt very bad about it.”
In the end, Rodriguez said, he harbors a faith that Milito was not involved with the Merriam slaying.
“In the bottom of my heart,” the former police superintendent said, “I have 100 percent hope.”
———-
Monday: The unsolved slaying of Charles Merriam.