Gallows humor? Accused cop killers say some email between police bosses raises red flags

It did not take long for the Chicago Police Department to blame Spanish Cobras for Officer Clifton Lewis’s murder.

Within a week of the 2011 killing, CPD had arrested three of the gang’s members, calling them the gunmen and getaway driver. But prosecutors found the case against one of the alleged shooters — Alexander Villa, known as “Flip” — was lacking and refused to file charges.

After Villa’s release, CPD kept trying to strengthen the case against him. The efforts involved a joint operation with federal authorities. The operation, dubbed Snake Doctor, sought to dismantle the gang and generate witnesses against Villa, according to internal police records obtained by his attorney.

Within five weeks of the killing, police had arrested 122 people tied to the gang, according to a CPD deputy chief’s tally. As months passed, CPD kept the heat on the Cobras and kept questioning the arrestees about Villa, a routine that became known among some cops as the “Flip speech.”

Jennifer Blagg, Villa’s attorney, claims another ritual emerged: Police telling arrested gang members that Villa himself was responsible for their trouble — that he was a snitch — to win their cooperation against him.

Now an email exchange between police bosses tied to the investigation is adding weight to Blagg’s claim.

The exchange, attached to a new court filing by one of the defendants, took place May 24, 2013. Christopher J. Kennedy, at the time a commander who led CPD’s Gang Investigations Division, wrote to some underlings that Villa had been stabbed the night before as he exited a Rosemont movie theater with a friend.

The attack put Villa in the hospital with multiple stab wounds.

“Not gonna croak though,” Kennedy wrote.

The commander’s email led to a response from Lt. Scott Dedore.

“I believe Operation ‘Snake Doctor’ and 6580 has to take the credit for this,” Dedore wrote, using the number of a team within the division.

Dedore referred to Sgt. Matthew Cline, a colleague working on the investigation, who is now a CPD deputy chief.

“Cline and company tell each Cobra that, every time a Cobra goes to jail, it’s Flip’s fault,” Dedore wrote.

“Unless I got the facts wrong,” Dedore added, “Flip was targeted by other Cobras. His associate was left unscathed. It sounds like … the Cobras are getting the word.”

Kennedy replied with a semicolon followed by a closing parenthesis, a pairing known as a winky face.

Blagg, who unearthed the communication, said it’s more than gallows humor.

“This email exchange shows that the Chicago Police Department’s Gang Investigations Division is no different than a Chicago street gang,” Blagg said. “One of their own [Lewis] was harmed and they sought retaliation. They either wanted my client [Villa] to be killed by a fellow gang member or to induce a fellow gang member to testify against Villa in the Lewis homicide.”

“They wanted to get him, one way or the other,” she said.

In the court filing that revealed the email exchange, Paul Vickrey — an attorney for Edgardo Colon, the alleged getaway driver — wrote of “criminal implications for every member of Operation Snake Doctor that purposely sought to have Villa harmed.”

Kennedy, now the police chief of north suburban Northbrook, declined to comment.

Dedore and Cline, who remain CPD members, did not respond to requests for comment.

A department spokesman said there would be no comment from CPD because the cases stemming from the Lewis murder remain active.

Alleged prosecutorial misconduct

Lewis was shot on Dec. 29, 2011, as he worked a second job as a security guard in a West Side convenience store.

A jury convicted Colon of charges including first-degree murder, but an Illinois appellate court in 2020 ordered a new trial due to police having questioned him after he said he wanted a lawyer.

Tyrone Clay, one of the alleged gunmen, has spent nearly 11 years in jail without trial. In 2020, an appellate court affirmed a judge’s ruling that threw out his videotaped statements to police, finding he could not have waived his Miranda rights due to what his attorneys described as limited intelligence.

In 2013, Villa was charged with first-degree murder in Lewis’s killing. A jury convicted him in 2019 but he has not been sentenced. He remains in jail and is pressing for a new trial.

In recent months, the cases have focused on evidence production and allegations of police and prosecutorial misconduct. A hearing on Tuesday centered on what attorneys for Colon and Clay have called the Police Department’s “decadelong effort to hide exculpatory evidence,” an accusation that attorneys for CPD disputed.

In January, Cook County State’s Attorney Kim Foxx yanked the longtime prosecutors in the cases after allegations that those veteran attorneys were trying to hide evidence when they used private email accounts in 2012 and 2013 to communicate with detectives investigating the case.