Attorney says the money can be taken as payment toward judgement
You can take Joe Carollo, out of City Hall, but you can’t get City Hall to forget Joe Carollo.
The former Miami commissioner will always have an ongoing saga at the Dinner Key theater, and Thursday was no different. What was supposed to be a relatively quiet vote approving a $770,000 settlement payout to Carollo suddenly detonated into courtroom drama, emergency motions, accusations of legal gymnastics, whispered panic inside City Hall and — because this is Miami — another shade meeting request.
Ay por favor.
By Thursday morning, the item that only days earlier appeared headed toward easy approval of the six-figure payout was abruptly pulled from the agenda after attorneys for Little Havana businessmen Bill Fuller and Martin Pinilla stormed federal court the night before demanding the city freeze the payment before Carollo could get his cafecito-stained hands on it.
And suddenly everybody at City Hall developed a severe case of procedural caution.
Funny how that happens.
Read related: Miami’s Joe Carollo swoops in to snatch $770K from city funds in a settlement
The emergency filing by attorney Jeff Gutchess basically accused the City of Miami of trying to perform a legal shell game to protect Crazy Joe from the $63.5 million federal judgment he still owes Fuller and Pinilla after a jury found he weaponized city government against them in a 
political retaliation campaign. That was in 2023, after he spent years targeting their tenants and shut down Ball and Chain on Calle Ocho because they had an event for a political opponent.
Remember, this is the same city that spent years defending Carollo in court with taxpayer dollars. The same city now publicly trying to recover some of those legal expenses. The same city that, according to las malas lenguas, has spent months quietly trying to structure this settlement in a way that would keep the money safely out of the plaintiffs’ reach.
Because apparently in Miami, even retirement payouts need asset-protection strategies.
The whole legal fight now boils down to one deceptively simple question: Is this protected pension money? Or is it just a regular litigation settlement dressed up in pension clothing?
See, Carollo’s lawsuit dates back to 2006, when he sued the city claiming changes to the elected officials pension system improperly reduced his benefits after his two mayoral term and three commission terms. The case sat around collecting dust for nearly two decades before suddenly roaring back to life the minute Carollo left office under the warm glow of term limits, federal judgments and general public humiliation.
Now the city wants to settle. Conveniently.
According to Gutchess, the proposed payout would come from city general revenues — not directly from a protected retirement trust — meaning it may not qualify for the legal protections the city has been relying on while arguing Fuller and Pinilla can’t touch it. The city, he said, is trying to sneak Carollo the payday.
“What is deeply troubling,” Gutchess said in a statement Thursday, “is that, even after the jury’s findings and the Court’s judgment, the City of 
Miami continues to aid and abet the very individual found liable for weaponizing government power against private citizens.”
En otras palabras: Why is the city helping Joe Carollo hide money from taxpayers he already lost to in court?
After commissioners voted to defer the item, Gutchess — who did not return Ladra’s calls — told WPLG Local 10 that Carollo still seemed to “wield extraordinary influence over the machinery of city government,” including, or perhaps especially, the city attorney’s office. “Today’s cancellation of the vote only raises more serious questions about what has been happening behind closed doors at City Hall over the past several months,” he said.
Read related: How can Miami’s Joe Carollo pay $63.5 million damages in federal jury award?
“Based on the information we have uncovered, it appears that the City Attorney’s Office, working in coordination with Commissioner Carollo and his private counsel, has been attempting to structure and characterize this payment in a manner designed to shield it from lawful collection efforts tied to the outstanding federal judgment. The conduct we are seeing suggests very little has changed inside the City of Miami.“
An accusation like that would land like a grenade inside City Hall. Suddenly City Attorney George Wysong — who until recently seemed perfectly comfortable moving the settlement forward — announced to the press that the “prudent thing” would be to slow down and review the court filings.
Prudent. A word rarely heard inside Miami City Hall unless the FBI is already circling the block.
Meanwhile, the US. magistrate judge who got the case le halo las orejas a Gutchess for labeling the filing an “emergency,” noting the plaintiffs created the urgency themselves by waiting until the eve of the vote. Unless they were just finding out.
But the judge did not decide the underlying issue. The question of whether the money can legally be reached is still very much alive.
And apparently alive enough to send Commissioner Rolando Escalona requesting a closed-door shade meeting with the city’s lawyers to discuss 
the expanding universe of Carollo litigation currently hanging over taxpayers like Miami humidity.
Escalona later told reporters he simply wants to “close that chapter” and move on with his life in District 3, probably as if Carollo never happened.
Honestly, who can blame him? Joe Carollo could easily become the single most expensive former elected official in modern Miami history.
Read related: Supreme Court slams door on Joe Carollo’s appeal of $63.5 million verdict
There’s the $63.5 million verdict, on which he lost the final appeal in March. The ongoing insurance litigation over legal fees. The still-pending Fuller-related litigation headed toward trial next year. The recently settled whistleblower lawsuit involving Bayfront Park Management Trust insiders. The outside attorneys. The appeals. The investigations. The settlements.
The political damage.
And now, apparently, the pension payout that may trigger an entirely new legal war over whether taxpayers are financing Joe Carollo’s judgment-proof retirement strategy.
The truly amazing thing is that Carollo is no longer even in office.
Yet somehow City Hall still appears to orbit around him like a haunted tropical moon.
The item is now deferred until June 11.
Unless there’s more court action.
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