Tampa Mayor Jane Castor's 10 dumbest moments of 2022

Jane Castor filed for re-election earlier this month, a move that will likely solidify her position as the next mayor of Tampa since no other candidate has emerged with even a slight shot at the job. So, it's kind of remarkable that a mayor, who is all but guaranteed to be re-elected, could still, somehow, still have a year this jam-packed with scandals, controversy and all-round general stupidity.

Without a doubt 2022 was a tough one for Castor. From losing her handpicked police chief over a golf cart scandal, to losing her shirt over Bitcoin and then shilling for tech bros, here are Jane Castor's 10 dumbest moments of 2022.

1.  After a DOJ investigation and the displacement of hundreds of mostly Black residents, Castor blamed the media and staunchly defended her “Crime Free Housing” program.

Castor backed up her accusation that the media was wrong by citing incomplete data gathering conducted by her administration which only examined a portion of the time “crime free” existed.

The city’s assessment is missing the first three years of data, when the program was most active. There were also a number of other problems with the data.

"The majority of notices sent to landlords were for someone living with the registered tenant, so the names would not match in court documents," the Times published in defense of its reporting last year.

"And in many cases, families moved out when they received a notice to vacate or were told to do so by the landlord — before the matter went to court."

Documents obtained by Creative Loafing Tampa Bay support the Times’ statement, with one note from TPD reading, "left on her own—no eviction."

Another TPD document notes that a landlord chose non-renewal of the tenant's lease, rather than eviction.

The city's data gathering did not address these types of situations. Under “crime free,” if a person was even arrested for a crime, the whole household could be evicted, including the elderly, children and other family members.

According to the Times investigation, TPD officers recorded more than 300 tenants as “evicted” on a database which tracked the activity of the program.

2. Castor waited over five months to admit she approved the Hanna Avenue project, which somehow ballooned from $10 million to $108 million without a public bid.

Yesterday, Mayor Jane Castor said that she approved Tampa's 'City Center at Hanna Avenue' after more than five months of councilmen and local leaders asking who was responsible for the controversial project.

Her admission comes after multiple city council meetings since November where construction experts and city council members repeatedly asked who was responsible for green lighting the project, which jumped from $10 million to $108 million without a public bid, among other glaring problems—including initial lack of participation from unions and the Black community.

Not only did Castor avoid answering the community's important question until yesterday, her city attorneys pushed back on the idea of appearing before council to discuss the project back in March.

Eventually, though, staff did discuss the project. At a city council meeting on March 31, Castor's Chief of Staff John Bennett said, "The administration brought this together collectively and made the best decision we could at the time."
Castor condemned former councilman Dingfelder for using private email for city business, but didn’t care city attorney used a private cell to discuss the exact same matter.

3. After Castor ripped former councilman John Dingfelder for using a private email to conduct city business, Tampa's city attorney was caught using a private cell phone ... to discuss the Dingfelder case, and other city business.

Documents show that Tampa's City Attorney used her personal cellphone to communicate with an attorney, who just months ago sued former councilman John Dingfelder, in part, for using a personal email.

Despite telling City Council members to not use their personal phones for city business, City Attorney Gina Grimes used hers to stay in regular contact with attorney Ethan Loeb during hours of phone calls between December and March of this year, according to documents obtained by Creative Loafing Tampa Bay.

Last October, Loeb filed a public records lawsuit against Dingfelder, which ultimately led to his resignation as part of the the lawsuit settlement.

Texts to her personal cell show Grimes indicating when she was available to talk with Loeb. And some of the data from conversations about city business, which is required to be retained by the city and provided under public records law, were not available in the city's records.

Grimes, who worked for a real estate and land use firm from 2004-2019 before joining Mayor Jane Castor's administration, also used her personal cell to discuss a property in Tampa city limits with Steven Michelini, a consultant for developer Jon Lum. The public records lawsuit that forced Dingfelder to resign as part of the settlement terms was filed on behalf of Michelini, with Loeb as the prosecuting attorney.

4. Castor conveniently claimed “rent control would kill development," while more than half of her re-election PAC is lined with developer cash.

At a March 9 press conference, Tampa Mayor Jane Castor told reporters that rent stabilization and rent control aren't viable solutions to the housing crisis because the measures would "kill development."

What Castor didn't mention is that over half of her "Tampa Strong" political action committee (PAC) is funded by sources tied to development.

Records from the Florida Division of Elections website show that, $539,950 out of $1,039,180.93—roughly 52%— came from donors who fit into categories aligned with industries associated with development.

These categories include: real estate and construction firms, private equity firms, real estate attorneys, engineering firms and developers.

Real estate firms gave the most out of all of these categories, coming in at $323,350. Contributions from construction groups came in second at $128,600.

Tampa Bay Lightning owner and local mega-developer Jeff Vinik gave $194,000, or 18.6% of the funding for the PAC.

5. Castor defended embattled HART CEO, and claimed she didn’t know anything about the toxic work environment claims, despite months of reporting from multiple outlets.

Castor said she hadn't heard evidence of a hostile work environment, despite former employees saying it on the record, and a leaked resignation letter from Le Grand's fourth communications director that called Le Grand a "dictator and a tyrant."

Castor also said that she hasn't seen evidence of double-dipping by a top executive at HART, despite the Tampa Bay Times reporting on it last month.

What Castor said at today's meeting echoes what she said at a meeting last week, where she advised the board to not suspend or remove Le Grand. Castor used herself as an example, saying, "I've been involved in a lot of investigations in my lifetime."

Castor's defense of Le Grand happened on the same day that she accepted Police Chief Mary O'Connor's resignation. Castor requested the resignation after Creative Loafing Tampa Bay unearthed body camera video of O'Connor using her status to get out of a traffic stop. Earlier this year, Castor pushed for O'Connor to be police chief, despite a chorus of concern over O'Connor punching a cop during a 1995 DUI stop.

6. Despite nearly everyone screaming  not to pick a chief who previously fought a cop at a DUI stop, Castor’s handpicked choice to run TPD resigned in disgrace over a golf cart scandal.

O’Connor submitted her resignation less than a week after public records requests by Creative Loafing Tampa Bay unearthed body cam video showing her flashing her badge to get out of a traffic violation on a golf cart.

A press release says Tampa Mayor Jane Castor—who appointed O’Connor just nine months ago despite a contentious police chief search and pushback from the community—requested and accepted O’Connor’s resignation.

...

Her confirmation followed heavy criticism regarding lack of transparency by the mayor in the selection process, and concerns over a 1995 incident where O’Connor assaulted a Hillsborough County Sheriff’s deputy during a DUI stop.

During the incident, O’Connor, who at the time was an officer with TPD, was riding in the passenger seat of a car when her future husband, Keith, was pulled over on suspicion of DUI by a Hillsborough County Sheriff deputy. Keith—at the wheel again during this latest incident—was charged with drunk driving, and deputies claimed O'Connor kicked the windows and punched a deputy when she was put in the back seat of a patrol car.

The future police chief was charged with assault on an officer, obstruction and disorderly intoxication.

"This is especially disappointing because I gave Mary O’Connor a second chance, as I believe in second chances for people," Castor continued in the release. "Which is one of the reasons that the disappointment today runs so deep. I had high hope for Chief O’Connor, as she was off to such a strong start by reducing violent gun crime, proactively engaging with our community and focusing on officer wellness. But these accomplishments pale in comparison to the priority I place on integrity.”

7. City of Tampa settled a lawsuit against Councilman Orlando Gudes for a record $200,000, just two months before the case was dismissed.

A civil lawsuit against Tampa City Councilman Orlando Gudes has been dismissed, two months after the City of Tampa announced a separate $200,000 settlement for Gudes’ accuser.

In March, allegations against Gudes, which the city knew about since 2019, resurfaced. The councilman was accused of creating a toxic work environment and of sexual harassment by his former aide, who alleged that he used lewd language toward the them and their child.

After firing their previous lawyer Grady C. Irvin, the accuser obtained legal counsel of Ethan Loeb, the same development and business lawyer who sued former councilman John Dingfelder out of office.

Upon reviewing the arguments of both legal teams, a Hillsborough County judge dismissed the case this week.

8. Castor lost 67% of one of her paychecks to Bitcoin, only to continue to shill for the crypto ponzi scheme a few months later.

Yesterday, the mayor attended the opening of CoinFlip's new "Crypto Experience Center" in downtown Tampa's Sparkman Wharf and informed residents that the new business has "got it all."

"The new Crypto Experience Center has such a unique approach to educating people on bitcoin & leveling the playing field for EVERYONE who is interested to learn & invest," tweeted Castor Tuesday afternoon.

The mayor's appearance at the event comes after the fact that her current crypto wallet, or at least part of it, took a giant hit.

Last November, Castor hosted the Bitcoin and Blockchain Summit in Tampa and told media outlets that she would accept two paychecks in the form of Bitcoin, following other mayors, like Miami's Francis Suarez, who also jumped on the crypto-bandwagon.

“Apologies for coming late to the conversation,” Castor tweeted in response to Suarez’s paycheck Bitcoin conversion announcement from Nov. 2. “But I’m certainly up for the challenge."

According to public records, Castor's annual salary in 2021 was $170,539. So, assuming she was paid bi-weekly, then one paycheck before taxes and other withholdings, comes out to approximately $6,559.

Now, putting this much money into crypto last fall probably didn't seem that risky. To be fair, in November of 2021, Bitcoin was at a record high of $68,990, with tech bros predicting at the time it would surpass $100,000.

Of course, that growth didn't happen, and just about every cryptocurrency slumped to dismal levels last summer. Even today, the currency is valued at $20,147.80, which is a a massive drop from its November peak.

So, where did all that money go? Well, it was cashed out by people who purchased Bitcoin before you did, and most importantly, realized it's a pump-and-dump scheme before you did.

Unfortunately, Mayor Castor did not do this.

Smith told CL that Mayor Castor's paycheck is still invested in Bitcoin, which means if she converted it during that first week of November last year, according to the Bitcoin Profit Calculator, it would now be worth roughly $2,117, a loss of $4,441.

9. After unprecedented friction with city council, local leaders (including Tampa’s first woman mayor) publicly dragged Castor, and stated that she needs to be “more transparent and less defensive”.

Sandy Freedman was the city's first woman mayor, taking the position over from former mayor Bob Martinez in 1986. Before that, she served on City Council from 1974 and then as Council Chair from 1983-1986. After completing the remainder of Martinez's term, Freedman was twice elected Mayor of Tampa, serving from 1987-1995, so she's seen what it's like to be on both sides of city hall.

"The city council certainly needs to pay close attention to things and they need to speak up when they see something that they don't think feels right, or in the public interest," Freedman told CL. "And on the other side, the mayor's administration itself has to be more transparent and less defensive. The mayor has to break bread with council members. We can't have our elected officials lashing out at each other."

Freedman said she would regularly discuss issues with council during her time as mayor. Meanwhile, multiple Tampa City Council members have claimed that Castor rarely communicates with them, even about important issues.

"Civil discourse only occurs when people have a level of trust. And the only way to build that is to do it quietly," Freedman said.

While Castor's administration has called for transparency and accountability from council, some have pointed out that there needs to be more of that from the administration itself.

Yvette Lewis, President of the NAACP Hillsborough County Branch, said she welcomes open talks with the mayor.

"I was glad to see Mayor Castor finally talk about transparency," Lewis wrote in an email. "It is past time for transparency in this administration. I would like to see transparency in civil rights complaints, employment discrimination, affordable housing, MBE participation, neighborhood development in East Tampa, police misconduct, police lawsuit settlements, and many more. What took so long?"           

10. Castor wouldn’t apologize to a family whose father died in the hands of TPD, marking a trend of refusing to apologize for TPD's actions.

Tampa Mayor Jane Castor doesn't seem concerned with the healing power of apologies, at least when it comes to the way the Tampa Police Department has harmed the Black community.

She has yet to apologize to the family of Arthur Green Jr., who died while restrained by TPD as he was having a diabetic emergency in 2014.

Last week, WTSP reported that the city has now settled an eight-year lawsuit with the family, who accused two TPD officers of using excessive force while trying to arrest Green as they failed to recognize he was having a medical emergency.

As part of the settlement, Green’s family said they requested an official apology from Castor, who was police chief at the time of his death, but she refused.

“The Tampa police didn’t treat our dad like a human being,” Arthur Green's stepson Kurt Young told Creative Loafing Tampa Bay. “And it’s deplorable that Jane Castor is trying to avoid accountability for that.”

Young said that he was raised by Green just like a biological son, and pointed out that he was a beacon of hope for the community and a mentor to many. Young said that TPD’s initial response was to try to vilify his dad, to avoid taking responsibility for what the police did to him.

“Castor had the chance to apologize and be on the right side of history, but she’d rather try to uphold this false narrative that my father was somehow in the wrong and that TPD acted according to policy,” Young said.

The Greens are just one of many Black families that have been affected by TPD's actions, especially when Castor was chief from 2009-2015.