City Hall has released a backlog of the mayor’s calendars. 

As you might guess, the calendars detail where the mayor goes and whom he meets. When he first took office, he released his calendars weekly. That pace slowed to monthly. Then it dragged even more. Until this week, the most recently available calendar was March 2025. 

After Weekly Chatter asked about the delay, the city released Bibb’s calendars from April through October. Here are a few appointments of note from the last seven months. 

Bibb, who is president of the Democratic Mayors Association, put in time with national figures in the Democratic Party. He had breakfast with U.S. Rep. Ro Khanna when the California congressman was in town for a City Club of Cleveland appearance in April. 

The mayor’s calendar for June 17 includes a phone call with Illinois Gov. JB Pritzker, a possible 2028 presidential contender. Bibb and Pritzker are co-chairs of the climate organization America Is All In. 

Bibb also met with investors and business leaders around North America. His June 6 calendar lists a meeting with an executive from the asset manager BlackRock during a conference in New York City.

The mayor had two days of meetings scheduled in September at a commercial real estate conference in Toronto, which came a day after the city shut down a bar in the Flats following a shooting.

In October, the mayor had meetings scheduled in San Francisco with executives at the software company Salesforce. Those were during the company’s Dreamforce artificial intelligence conference. Bibb also set aside time for a meeting with San Francisco Mayor Daniel Lurie.

The calendars offer a small glimpse at how Bibb prepared to break the post-election news that the Cleveland Metropolitan School District would seek to merge 39 schools. He scheduled a “CMSD messaging prep” meeting on Oct. 28. 

Then on Oct. 31, Bibb and CMSD CEO Warren Morgan had a call scheduled with Gov. Mike DeWine. The calendar entry does not say whether the topic was school consolidations or something else. 

Bibb’s meeting over Coca-Cola with Jimmy Haslam to strike an exit deal for the Browns does not explicitly appear in his calendars. But there is an hour-long block in the afternoon of Oct. 10 labeled “DNS,” or “do not schedule.” Over the weekend, the mayor and top staff had two “settlement planning discussion” meetings. 

Here are two other meetings that caught Weekly Chatter’s attention. On Aug. 29, Bibb’s schedules show a Zoom meeting with Don Garber, the commissioner of Major League Soccer. 

And at the end of September, the mayor and Police Chief Dorothy Todd were scheduled for what was termed a “Flock product presentation.” The city is proposing a $2 million, three-year contract with Flock Safety for gunshot detection, license plate readers and other police technology. 

Intel on AI at City Hall

The Bibb administration is thinking about how to bring artificial intelligence to City Hall. 

At Futureland, a local technology conference that met at the Museum of Contemporary Art this week, the mayor laid out a few ways he’d like to incorporate AI into the city’s work. 

The city is testing out using AI to survey the conditions of neighborhood homes. Staff are also putting together a “management dashboard” that would involve AI in tracking city operations and public safety, Bibb said. 

The mayor floated the idea of using AI chatbots to help 311 call-takers handle resident complaints about everything from potholes to groundhogs. His administration plans to educate employees on how they can use AI in their work, he said. 

“If the city is using AI to make sure we demolish vacant homes faster, that’s progress,” Bibb said. “If the city is using AI to make sure that our call center agents are responding to pothole complaints faster, that’s progress.”

Joining the mayor on the Futureland panel was Winton Steward, the Midwest head of government affairs and public policy for Google. The moderator was Shanelle Smith Whigham, the national community engagement director at KeyBank and a recent Bibb appointee to the Greater Cleveland Regional Transit Authority board.