Over a week ago, then-chief of staff Jay Black, Jr., called up the president of the city's police patrol officer's union and brought up a few points he was determined to have addressed.
The fact that he used a false name, and was subsequently revealed, earned him a suspension and eventually led to his resignation last week.
Following the resignation, friends and colleagues noted two key features of Mr. Black that may have contributed to that ill-fated phone call: His strong sense of loyalty, and his ongoing rocky relationship with city unions - a relationship he was unaccustomed to while working in the private sector.
"He was a good soldier - and that's what this is about," said school board president Larry Sykes, a longtime friend of Mr. Black's, referring to Mr. Black's decision to call the television show. "He got caught up in trying to defend the mayor."
Mr. Sykes helped kick off Mr. Black's start in a successful career in banking, which after several decades culminated in an eight-year stint as vice president of National City Bank.
One of the reasons Mr. Sykes recommended Mr. Black to Mayor Jack Ford for the city position, in fact, was his belief in Mr. Black's strong sense of loyalty.
That hard-line loyalty also was evident when dealing with other city officials, particularly city council.
"I think at times he thought we worked for the mayor.. Mr. Black had a large learning curve to overcome when he came on," said city council president Louis Escobar. "Mr. Black didn't understand that one of the roles of council was to question. At the very beginning, he didn't understand why we were asking questions."
"He had never worked in the public service, with unions, or government," Mr. Escobar said. "In the private sector, you're able to say, `this is what I want.' That's not how government works."
Lucas County Administrator Mike Beazley, who worked closely with Mr. Black while serving as clerk of council until the beginning of last year, noted "there's always conflict between mayor and council; it's the nature of the business," but nonetheless said he always had a "good, strong relationship" with Mr. Black.
And city council member Karyn McConnell Hancock said she thought Mr. Black "always did a great job of getting both sides and getting all the issues hashed out. I knew him to be very fair and very diligent in the work that he did."
"Jay was effective for Jack Ford. He did what was expected of him," Mr. Escobar said.
But councilman Bob McCloskey said he had a rocky relationship with Mr. Black.
"I don't think he was an effective chief at all - I think an effective chief of staff would have made a strong point to work with council, work on communications, worked the unions," Mr. McCloskey said. "He had a very, very rocky relationship with the unions. It made our job a little tougher: That was probably the biggest setback."
"The unions would come to us and complain, and I would have to remind them that they were dealing with somebody new," Mr. Escobar said.
Gregg Harris, president of the Toledo Police Patrolman's Association - the man who Mr. Black called on television - said he had no problems personally with Mr. Black, though he described their relationship as "strained."
"To be totally honest, I felt that he would come at you like he wanted to sit down with you, but I always had that feeling that he was never really going to give my ideas consideration," Mr. Harris said. "We certainly didn't agree on contractual issues - most people will agree that's the nature of the beast - but we've had more grievances than we've ever had."
Their on-air dialogue related to jobs, and Mr. Black's offense at Mr. Harris' omission that Mayor Ford had not laid off officers, as other cities had done in hard fiscal times.
When the two met in person after Mr. Black's phoned-in comments on television, Mr. Harris said Mr. Black "acted totally different than all the other times I dealt with him. He was very sincere. He said he did it because he was very upset with me for not giving out the whole story."
Don Czerniak, president of the American Federation of State, County, and Municipal Employees Local 7 - the city's largest employee union - said "there was some working relationship" with Mr. Black.
But he quickly added that he and Mr. Black "did bang heads quite a bit. Jay was like, we'll deal with the unions when we need them.. As long as we were going to bed and playing yes-man we were all right - but otherwise, there was a conflict."
"Labor relations are especially difficult in tough fiscal times. It leads to minor incidents becoming major obstacles," noted Mr. Beazley. "Because of the finances, they had the smallest wage increases in 20 years. It's hard to be the popular guy when that's happening."
City spokesman Mary Chris Skeldon, who was notably saddened by Mr. Black's resignation, said she "very much enjoyed working with Mr. Black."
"Jay Black is an extremely hard worker who was sometimes tough, but fair. Personally, what I think of when I think of Jay Black: He was a perfect gentleman," she said.
Mr. Black did not return calls for comment on this story.
Contact Tad Vezner at: email@example.com or 419-724-6050.