When Jared Kupiec resigned as Mayor Pedro Segarra's chief of staff on June 3, he was the fourth high-ranking city official to leave in the past year.
Kupiec's exit was the latest in a string of departures that included the fire chief and chief operating officer. Key leadership positions in the human resources and information technology offices also haven't been filled.
But, far from being concerned, Segarra said he sees the openings as an opportunity to recalibrate and rebuild his administration, and to improve communication ? something considered lacking in areas of city government.
"It's time for me to evaluate what's working and what can be improved," Segarra said. "We are going to look carefully at all aspects of city government and push ourselves to work more efficiently and effectively to address the burdens our taxpayers face."
It's been a difficult year for Segarra. Last winter, his collaboration with the city council began to dissolve. The legislative body, which once approved most appointments and initiatives put forth by the mayor, began to rebuff his ideas. Members said they weren't getting enough information beforehand, and they hadn't been approached for their own thoughts and opinions.
At the same time, Kupiec ? considered the mayor's liaison to state and local politicians ? didn't develop relationships with councilors and was often at odds with the city's former chief operating officer, David Panagore, observers said.
Segarra and other city leaders are now working to repair some of the damaged relationships.
"Obviously, there will still be disagreements," said Juan Figueroa, a former state representative who is serving as the mayor's interim chief of staff, "but, ultimately, it's finding out what can be done and compromising so we can service the residents of this city."
While Segarra's relationships with some council members began to unravel earlier this year, rapport with others was never established to begin with, observers said.
"We weren't speaking to each other, we were speaking at each other," Councilman Kenneth Kennedy, a Democrat, recalled. "The mayor and the council's relationship really got off course."
Kupiec, 30, worked as a deputy campaign manager for former gubernatorial candidate Ned Lamont before being hired by Segarra in 2010.
"He didn't come into the job with a host of local relationships," Shawn Wooden, the council president, said of Kupiec. "I'd like to see dramatic improvements between the chief of staff and council in terms of communication and the timeliness of what's communicated. We want to know what's happening with major initiatives, what's happening with city departments."
Kupiec did not return a call seeking comment for this story.
Council members, who are charged with approving several key mayoral appointments, said they haven't been asked to provide input on candidates for the open positions and were notified of the mayor's selections only a short time before the public became aware of them.
"I don't think the mayor has been very inclusive with some of the decisions he's made," Kennedy said, "and he hasn't taken the council into account when proposing major budget or policy initiatives."
Councilors in April indicated that they would not approve Segarra's top choices for chief operating officer and corporation counsel ? Saundra Kee Borges and Figueroa, respectively. Council members said at the time that they weren't consulted about the appointments and didn't like the direction the administration was going in. The mayor later withdrew his nominations.
Kee Borges, a former city manager, has been Hartford's corporation counsel since 2010. Figueroa worked previously as president of Connecticut's Universal Health Care Foundation and general counsel of the Puerto Rican Legal Defense and Education Fund.
"You can't keep a big appointment a secret because someone might disagree with you," Kennedy said. "I just saw some arrogance that basically conveyed: We're the government, we can do what we want."
Relationships within the administration were strained as well. Panagore, the former chief operating officer, said that he and the chief of staff both reported directly to the mayor. And although one is a political appointment and the other is not, the city charter isn't clear about which one has authority over the other. Some responsibilities overlap, he said.