A trove of emails released by Mayor Rahm Emanuel shows him routinely using his personal accounts to conduct city business– receiving updates on crime, chatting cattily with powerbrokers, monitoring his press coverage and soaking in flattery from aides.

The communications, contained in hundreds of emails made public by Emanuel after battling to keep them under wraps in a yearlong legal dispute with the Better Government Association, show a mayor who gave special access to those with political power and influence as well as imagemakers including select journalists. Many city employees and key community members also for years used the mayor’s personal email accounts to converse with him.  

But what is largely absent from the emails is correspondence concerning key controversies of his administration—the Laquan McDonald shooting video controversy, the principal training scandal that led to the criminal conviction of his hand-picked school superintendent, the 2012 teachers strike or the chronic financial woes of the city and sister agencies.

The BGA has not yet determined whether emails discussing those subjects were withheld on the basis of legal exemptions which could apply to any public records, or whether such documents exist separately on city email accounts of the mayor or his staff.

Emanuel first took the oath of office as mayor in May 2011, and from the start of his administration he pledged that the city under his leadership would be among the most transparent governments in the nation.

The reality has been quite different. Accessing public records – especially documents about politically hot topics or those pertaining directly to Emanuel himself – has often been met with delays, obfuscation or court battles, including 11 open-records lawsuits by the BGA since 2014.

Emanuel released the emails from his personal accounts to settle a lawsuit filed in the fall of 2015 by the BGA. A similar but not identical lawsuit was also filed earlier by The Chicago Tribune. The suits alleged that Emanuel was using personal email and phones to conduct government business without scrutiny.

Use of government phones or email accounts would be generally subject to disclosure under open records laws.

Though not acknowledging wrongdoing, as is typical in legal settlements, Emanuel’s administration agreed to release emails from his personal accounts. The determination of which emails were strictly private in nature or which related to public business and were responsive to the BGA’s request were made by Emanuel’s attorney Michael Forde. 

Through his attorney, the mayor provided a legally binding representation that all such emails were provided to the city for ultimate production to the public, except where a legal exemption applies. The process mirrors the way public bodies are required to respond to open records requests on their computer servers. 

The BGA retains the legal right to re-open its lawsuit if it later comes to believe that the administration misrepresented what was done to determine what emails on the mayor’s accounts were public in nature.

Many that were released included large sections of redactions, which appeared to black out email addresses, talking points and responses from the mayor to queries of others. BGA is in the process of determining whether these redactions were proper and will address any that are not.

What’s more, the administration said Emanuel’s personal email accounts had been programmed to auto-delete files after 90 days, but that the auto-delete was turned off upon the filing of the BGA and Tribune lawsuits. That means that hundreds, perhaps thousands, of his emails had already been erased before the suit was filed and presumably before Forde ever looked at them, though the city said some in which he communicated with mayoral underlings were recaptured from city email archives.

As part of the settlement, Emanuel agreed in the future to forward all personal emails in which he discussed government business to the city so they can be subject to public disclosure if they meet criteria laid out in open records law. The administration also agreed to subject all employees to discipline if in the future they conduct personal business on public email and fail to then forward that to the city for archiving. 

Emanuel’s email situation is in many ways analogous to that faced by former Democratic Presidential candidate Hillary Clinton, a close friend and political ally of the mayor who served as a top aide in the administration of Clinton’s husband, President Bill Clinton.

Hillary Clinton’s campaign was dogged by controversy over her use of a private email server while Secretary of State in the Obama Administration as well as the way her attorneys oversaw the eventual process of deciding what was public and what purely private.

The email lawsuits against Emanuel were filed just months before a judge in a separate case found the city had violated open records law and ordered release of video showing a Chicago police officer shooting McDonald, an African-American teenager, 16 times in October 2014.

For a year after the shooting, the city fought requests from the public and media for release of copies of videos of the shooting from cameras attached to the dashboards of responding police vehicles. The resistance continued even after Emanuel and the City Council agreed to a $5 million settlement with McDonald’s family without a lawsuit even being filed.  

When the city did finally release the video, it was in response to a court order in a suit filed by an independent journalist. 

Routinely, his administration releases documents or press releases on sensitive or controversial topics on Friday afternoons as weekend’s gear up and attention spans of city residents may drift from the news cycle. Last year, after the McDonald video spurred follow-up requests for city emails related to the shooting from reporters and the public, the documents were released on New Year’s Eve, around a month after the request for the documents had been made.

The latest release of personal emails came just ahead of the Christmas holiday.

In their lawsuits, the BGA and the Tribune argued Emanuel was circumventing open records laws by using personal phones and email accounts that allowed him to conduct city business without scrutiny. The city argued it could not turn over any emails from Emanuel’s personal accounts because the records do not reside on city email and phone accounts.

In recent rulings, however, judges overseeing the cases have rejected the city’s argument, saying that what matters most is not what type of device is being used – an official government email account or phone or a personal email account or phone – but the subject matter of the communication and whether it relates to official duties. If the subject is related to city business, and the email was sent or received by a government official acting as such, the records are considered public regardless of what device or account they were delivered on. 

As the battles played out in court, the Tribune reported in November that Emanuel used two personal email accounts, including a custom domain called “rahmemail.com,” to communicate with government leaders and other politicians. The Emanuel email accounts emerged as part of the thousands of emails that had been hacked from Hillary Clinton’s campaign chairman John Podesta and made public during the presidential campaign by WikiLeaks.

Ironically, the new emails released by Emanuel show that he frequently used the rahmemail.com domain to communicate with top Tribune editors as well as nationally renowned journalists from CNN, The New York Times and the Washington Post. An array of influential Chicagoans also used the mayor’s personal accounts to converse with him.

What is clear from the emails is that Emanuel had little reserve about using his personal accounts to conduct mayoral business.

Just this April, Emanuel had a friendly back and forth communication with billionaire hedge fund manager Ken Griffin after Griffin emailed with complaints about disrepair on the lakefront bike path, a shooting near the University of Chicago lab school and expensive damage to his vehicle after going over a speed bump.

Emanuel was quick to answer Griffin, who donated $400,000 to Emanuel’s 2015 reelection effort, and then separately emailed an assistant to set up a meeting to discuss the complaints.

In August of 2015, Emanuel emailed an official of investment banking firm Centerview Partners agreeing to meet to discuss how the company had helped in restructuring financially troubled municipalities. 

There are several emails from former Police Supt. Garry McCarthy notifying the mayor about victims of crime. There are also several emails from Emanuel to corporate titans as he tries to convince them to move businesses and jobs to the city. There are even communications about closing public schools over harsh winter weather.

Many of the emails are short and to the point. “How did the police work up in your area last night?” Emanuel emailed Ald. Tom Tunney (44). Tunney, apparently unsure whether he was being spoofed, responded not to Emanuel but to one of the mayor’s assistants, saying “Could this possibly be from Mayor Emanuel?”

While that might indicate some aldermen were unaware of Emanuel’s personal email address, others clearly knew it. One business leader conducted an email introduction between Emanuel and Brian Chesky, the founder of Airbnb in May 2014. Two years later, Airbnb was a focus of the mayor and the city council as they debated how to regulate the private home rental business, which Emanuel has defended.

Political supporters are also sprinkled throughout the emails. In Nov. 2014, one of Emanuel’s email addresses received an invitation to an anniversary party for PEAK6, a Chicago financial trading firm whose officials have donated more than $150,000 to the mayor’s campaign funds.

Then there is the email flattery. In August 2011, just months after Emanuel took office, he marched in the annual Bud Billiken parade, a development that had one of his press spokesman gushing.

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She informed Emanuel in an email that police and others in the crowd had been heard praising Emanuel’s endurance. “He’s so in shape – Daley could never do this,” Tarrah Cooper emailed her boss.

As a result of the BGA’s lawsuit and settlement, the mayor and all other city officials will be prohibited from having these kinds of communications through personal email accounts, and will be subject to discipline for violating the policy.

Search the document below by clicking the expand box in the lower left corner of the emails at the bottom of this story. The Document Cloud page allows you to search the email file.