Cynthia Donald, pictured, who often served as Johnson's driver, is said to have spent three hours in the company of the married dad-of-three on October 16
This is the first picture of the security guard filmed kissing and drinking with fired Chicago police chief Eddie Johnson hours before he fell asleep in his car.
Cynthia Donald, who often served as her boss' driver, is said to have spent three hours in the company of the married dad-of-three on October 16.
He was found at the wheel of his car at 12.30am the next morning, telling officers he'd had a 'few drinks' at dinner and pulled over because he was tired. Officers did not conduct any sobriety tests and let their boss drive home.
The fresh details emerged on the same day it was announced that Johnson, the city's top cop, would be retiring with immediate effect.
Johnson said in November he would be leaving the force in January. He was joined at the press conference by new mayor, Lori Lightfoot, and by his family.
But on Monday, after new details of his night out emerged, a furious Lightfoot fired him, explaining she would never have taken part in the public announcement if she had known what she now does about the night in question.
And by Wednesday Johnson had filed for retirement effective immediately, ABC 7 reports. The mayor's office said he officially 'retired from his career service rank'.
Johnson and Donald had been at Ceres Cafe, a bar known for its heavy pours in Chicago. According to The Chicago Sun Times, they were filmed kissing.
Johnson is said to have promoted Donald to join his team when he became the city's top cop in 2012.
Now, several city employees are under investigation for allegedly covering up the incident.
After spending 'hours' in the restaurant, the pair got into his car and Johnson drove Donald back to police HQ. He then attempted to drive home but stopped before making it the entire way.
Security guard Cynthia Donald, left, was filmed kissing and drinking with fired Chicago police chief Eddie Johnson, right hours before he fell asleep in his car in October
Johnson and Donald spent three hours inside Ceres Cafe, pictured, which is inside the Chicago Board of Trade Building. The restaurant is notorious for its heavy pours
When interviewed by the office of the inspector general as part of an investigation into the incident, Donald is said to have told them they were 'friends' but both had 'troubled marriages' and confided in one another about them.
She filed for divorce from her husband in 2018 and has not commented publicly since the fallout from their night at Ceres.
Ceres Cafe is notorious for its free pours. When DailyMail.com visited on Tuesday evening, one patron drinking a glass of red wine was surprised when a waiter poured another and told him: 'It's the end of the bottle, you may as well have this.'
The restaurant closes at 8pm weeknights and doesn't open at all at weekends. Johnson was not found asleep in his car until 12.30am. It is unclear what time he and the woman left the restaurant on October 16.
The new information emerged on Wednesday, a day after Johnson issued a statement to say he understood the mayor's decision but that his 'integrity' was in tact.
Johnson and his wife Nakia, who is also a cop, married in 2017. She has a son, and he has three children from a previous relationship.
A lawyer for Johnson did not immediately respond to DailyMail.com's inquiries on Wednesday morning.
He however told The Chicago Sun Times that Johnson had been forthcoming about the fact he was in Ceres on the night in question.
He also denied claims, made in the report, that Johnson tried to avoid being interviewed about it by the inspector general's office.
Johnson is shown with his wife Nakea, right in police uniform, her 10-year-old son, front, his son Daniel, directly behind him, other family members and Mayor Lightfoot, left, at a press conference on November 7 to announce his retirement
Mayor Lightfoot and his family had celebrated his long career and his commitment to the force after 31 years as an officer and more than three as superintendent back in November. Johnson said then he was retiring to spend more time with loved ones.
On Monday, however, Mayor Lightfoot said she would never have taken part in the press conference if she had known what she now does about the night in question.
She said Johnson was guilty of 'ethical lapses' and made 'intolerable' mistakes.
'Just like with the public, Eddie Johnson intentionally lied to me several times,' Lightfoot said.
She added: 'Even when I challenged him about the narrative he shared with me, he maintained that he was telling the truth. I now know definitively that he was not.
'Had I known these facts at the time, I would have relieved him of his duties as superintendent then and there. I certainly would not have participated in a celebratory press conference to announce his retirement.'
Johnson and his wife, Nakia Fenner, have been married since 2017. She is also a cop. They are shown left in November, after the incident. Johnson and his wife Nakia are shown right in 2016, before they were married, as he congratulated her at her graduation ceremony
Johnson's attorney said: 'That's not how he sees it, he respects her opinion and he feels she's entitled to that view but he's entitled to his reputation and there is no way that Eddie Johnson intentionally lied to the mayor. That's just not the case.'
He said in his statement on Tuesday that while he acknowledged the night in question was a 'mistake', he did not intentionally mislead anyone, as Lightfoot claimed.
Johnson is best known nationally for his stern handling of the Jussie Smollett case.
He was the first to publicly accuse Smollett of lying to police by saying he'd been attacked by two 'light-skinned' assailants as he walked home in the middle of the night.
Smollett is now suing the city and Johnson personally for malicious prosecution. The charges against him were sensationally dropped by State Attorney Kim Foxx's office in March.