Departed Tampa police chief’s husband has seen rapid rise at City Hall

TAMPA — Two years before Mary O’Connor was named as Tampa police chief, a reign that ended with her humiliating exit from public life earlier this month, her husband was hired to run the city’s neighborhood enhancement division — still known colloquially as code enforcement.

He faced no competition for the job and quickly rose in rank and pay, without a major restriction on where he had to live.

In October, Keith O’Connor’s title was changed from manager to director in Mayor Jane Castor’s administration, but the city kept him on a manager’s pay grade, according to city officials and public documents obtained by the Tampa Bay Times in response to a Dec. 2 records request.

That prevented O’Connor from triggering a requirement that he live within the city of Tampa, like many other employees with director as their title. So he was allowed to continue living in a gated community in Pinellas County.

That wrinkle came under scrutiny after he was pulled over by a Pinellas County sheriff’s deputy for driving an unlicensed golf cart with his wife on a public street. The release of the body-camera video, in which she identifies herself as the Tampa police chief and asks the deputy to “let us go,” prompted the political upheaval that led up to Mary O’Connor’s resignation.

Keith O’Connor, 55, was hired to be the neighborhood enhancement manager in February 2020 without the city advertising the position. No other candidates submitted resumes, city officials confirmed.

The neighborhood enhancement manager is an unclassified, at-will position, so the city was not required to advertise the job opening, said Castor’s chief of staff, John Bennett. He noted that the city does advertise to fill many unclassified job openings — as it is now for a purchasing director — but said he doesn’t know why the city didn’t before O’Connor was hired.

O’Connor retired as a deputy chief in the Tampa Police Department in August 2019, capping a 25-year career. Bennett, who also previously worked for the police department, said law enforcement experience likely played a role in O’Connor’s hiring for the new city gig. The previous two heads of code enforcement had been retired cops.

The job includes overseeing the city’s code enforcement program, which handles violations of city ordinances on everything from uncut grass to illegal home additions.

O’Connor was hired with a salary of $111,176. In October, O’Connor got a 4% percent pay bump, although his new job was described in city documents as a “title change.” Along with prior raises, that took his salary to $138,965 as director.

In two annual evaluations, his supervisor Ocea Wynn, the city’s administrator of neighborhood and community affairs, had given him outstanding marks, noting his people skills and “non-aggressive demeanor.” O’Connor’s media savvy was a “bonus,” she said, adding that he was very comfortable giving interviews.

“He is a natural,” Wynn wrote in both August 2021 and April 2022.

O’Connor, through the mayor’s office, declined an interview request, saying “the records speak for themselves.”

As early as October 2021, Wynn had recommended O’Connor be named director. She also recommended that Neighborhood Enhancement Division be reorganized as a department, with O’Connor in charge.

His promotion would come with a caveat, however.

“Keith understands that the requirement for this level is residency within city limits,” Wynn wrote in an Oct. 14 email to the city’s employment services manager and human resources director.

But the plan changed after Bennett, that same day, suggested that the city “retitle” the position, but keep it as a division director. He said O’Connor would still get the 4% raise.

The other option, Bennett said, was to wait until the next budget year for a departmental reorganization in which O’Connor could be made department head.

Wynn decided to go with the first option, but not until the following October, when the city’s new fiscal year started: O’Connor would be a director, but not a department head.

Bennett said neither Keith nor Mary O’Connor approached him about finding a way to skirt the residency requirement.

“It wouldn’t have been my place at that point. It was Ocea’s employee,” Bennett said.

Wynn declined an interview request to answer questions about why she hired O’Connor, if she sought other applicants and how she handled his title change.

In a statement relayed through a city spokesperson, Wynn said O’Connor was a good fit for the job because of his law enforcement background and knowledge of the city.

Only department directors, not division directors, are required to live in the city, Tampa officials said. And O’Connor’s salary is comparable to other nondepartment head directors, said city spokesperson Lauren Rozyla. According to the city’s organizational chart, dozens of high-ranking employees fall into that category.

“If he was a department head, he would make a good $30K more,” wrote Rozyla.

Added Castor spokesperson Adam Smith: “There is not one iota of evidence that there was anything unusual about Keith O’Connor’s hiring, title change, or residency status.”

Bennett said he didn’t know the details on why and how O’Connor had been hired, deferring to Wynn on questions about O’Connor’s hiring.

“I think (Keith) O’Connor was retiring from the police department. And there was an opportunity in code enforcement under a different portfolio. And when Ocea Wynn became the administrator, in early February of 2020, which would have been when we did our major reorganization, I think Keith O’Connor was hired by her,” Bennett said in a Dec. 12 interview.

“What we find typically is either ... that somebody in that managerial position usually has some sort of law enforcement background on their resume. But how she selected him for that specific role? I don’t know. I wasn’t on the selection process for that,” Bennett said.

At a Dec. 13 campaign kickoff for City Council candidate Janet Cruz, the mother of the mayor’s partner, Ana Cruz, Castor, the former Tampa police chief, said she considered O’Connor’s residency status to be a nonissue.

Asked how she thinks it looks to have the person in charge of Tampa code enforcement, which is charged with keeping the city looking good and and properties owners in compliance with city codes, living in a gated community in Pinellas County?

“We’ve got policies on who should and shouldn’t be (living in Tampa) and you got the answer to that,” the mayor said.