Chicago Police Supt. Garry McCarthy was said to be “shellshocked” by the news that his services were no longer required. Perhaps he can take comfort in knowing his has been a common fate among the city’s top cops through the years even though, publicly at least, the following superintendents “resigned.”
Phil Cline
In the spring of 2007, Chicago dreamed of the summer Olympics coming to the shores of Lake Michigan in 2016 — or at least Mayor Richard M. Daley did.

Supt. Phil Cline in 2007. | Sun-Times file photo
But videotape shown around the world of off-duty officer Anthony Abbate pummeling a female bartender didn’t exactly help the city’s chances.
Cline, who worked his way up through the ranks and spent 37 years with the department, offered his resignation and the mayor promptly accepted. Though Daley conceded it was “time for a change” at the top, he flatly denied he requested the superintendent’s resignation.
“Leaving during these times of challenge makes my decision even more difficult,” Cline said at the time. “Mayor Daley has given me a once-in-a-lifetime opportunity to lead the best police department in the country and I thank him for that.”
Matt Rodriguez
Here’s a good rule of thumb: If you’re the city’s top cop, don’t hang out with a convicted felon.

Police Supt. Matt Rodriguez in 1992. | Sun-Times file photo
“I did not willfully — as perhaps as preposterous as that may sound — actually, willfully, think I was violating Rule 47,” Matt Rodriguez said in November 1997, when he announced his resignation as superintendent. “You have an associate for quite a few years. I didn’t look at him as Frank the felon. He was a friend.”
The then-rarely enforced Rule 47 of the Chicago Police Department forbade “associating or fraternizing with any person known to have been convicted of any felony or misdemeanor, either state or federal, excluding traffic and municipal ordinance violations.”
Rodriquez stepped down following revelations of a long friendship with businessman Frank Milito, who had pleaded guilty to mail fraud more than 10 years earlier and served nine months in prison.
Richard Brzeczek

Mayor Byrne and Police Supt. Richard J. Brzeczek, with his two sons, salute police units passing the reviewing stand during a St. Jude Police League parade through the Loop. | File photo
When then-Mayor Jane Byrne lost the Democratic primary to Harold Washington in 1983, it became clear that Supt. Richard Brzeczek would be out with her.
Brzeczek had made a campaign commercial for Byrne and he said working for Washington would be the same as working for Jesse Jackson.
“I won’t work a day for that man,” Brzeczek said at the time. “He won’t have a chance to fire me. I’ll quit.”
Timothy J. O’Connor
In 1960, Richard Morrison, the so-called “Babbling Burglar,” was in the Cook County Jail, but facing serious prison time. He decided that if he was going to the Big House, he wasn’t going alone.

Police Commissioner Timothy J. O’Connor who appeared before the grand jury on a Police Traffic Probe sin 1960. Photo by Larry Nocerino, Chicago Sun-Times
“If I have to go to the penitentiary for 20 years,” he told investigators, “I’m going to take a lot of coppers with me.”
Six of the eight officers arrested in the Summerdale scandal went to prison for taking part in a burglary ring that saw cops placing orders for stolen goods—TVs were popular around World Series time—and carting them away in squad cars.
Chicago was horrified. Police CommissionerTimothy O’Connorresigned.
After the Summerdale scandal broke—carrying so much humiliation that the 20th police district changed its name— Mayor Richard J. Daley brought in reformer O.W. Wilson.