A handful of prominent players in South Florida’s real estate world spent 2025 in courtrooms, tangled in legal skirmishes that pitted power brokers, luxury brands and even a presidential legacy project against a cast of scorned investors, ousted owners and activist plaintiffs.
A developer fended off anonymous smear campaigns. A builder accused investors of a hostile takeover of a project. A disgraced lawyer accused his former employers, a Miami Beach real estate power couple, of turning him into a scapegoat in a public corruption probe. And one of Miami’s most prominent residential brokers and his wife settled a wrongful death lawsuit by the family of a college student that his wife ran over.
Here are the 10 juiciest South Florida lawsuits reported by The Real Deal in 2025:
Trump library land deal lands in court
The most high-profile legal fight over South Florida real estate involved a downtown Miami parking lot adjacent to the Freedom Tower linked to the 45th and 47th U.S. president, Donald Trump.
Local historian and activist Dr. Marvin Dunn sued Miami Dade College in November over its board of trustees handing over the 2.6-acre site — free of charge — for a potential Trump presidential library within a nearly $1 billion mixed-use project. Dunn accused the college’s trustees of violating Florida’s public records and public meetings laws by quietly approving the September transfer with vague notices and little discussion.
Miami-Dade Circuit Court Judge Mavel Ruiz issued a temporary injunction and set an August 2026 trial. But this month, the college held a do-over vote at a packed public hearing that was broadly advertised. The board again unanimously backed the transfer to a state board controlled by Gov. Ron DeSantis and Florida’s four Cabinet members, all of whom have already committed to transferring the land to the nonprofit foundation raising money for the presidential library project.
Ruiz ruled the second vote cured the violations and lifted the injunction. Her decision allowed the parcel, which reportedly has a market value of $60 million-plus, to move one step closer into Trump-branded history.
The Centners’ “fall guy”
January brought fresh legal trouble for David and Leila Centner, the politically connected private school operators and real estate investors. The Miami Beach couple, who own Centner Academy and have significant commercial real estate holdings in Miami, allegedly let their former lawyer and lobbyist William Riley Jr. “take the fall” for bribery and money laundering charges that state prosecutors brought against him last year, a pending lawsuit alleges. The criminal charges against him were dropped.
Riley is suing his former clients for damages over the loss of his reputation, his ability to practice law and the expenses he incurred while fighting the criminal charges since his arrest in 2023.
Riley was accused of funnelling $245,000 in illegal campaign contributions from a Centner entity to a political committee controlled by then-Miami City Commissioner Alex Diaz de la Portilla, who was also arrested and charged with bribery and money laundering. The affidavit contains excerpts of sworn statements by the Centners distancing themselves from the donations and the entity. The case was dropped after prosecutors determined the contributions were, in fact, legal.
Riley claims Leila Centner directed him to open the entity’s bank account, use it to buy real estate and fund political action committees. He alleges he followed her “specific and detailed instructions” on contributions. His lawsuit accuses the Centners of never making an effort to clear his name.
De la Vegas face wrongful death suit
In February, One Sotheby’s International Realty president Daniel de la Vega and his wife, Veronica Bilbao de la Vega, were hit with a wrongful death lawsuit over a fatal crash that killed University of Miami student Daniel Bishop near Coral Gables Senior High School.
Bishop’s estate, led by his parents, Susan and Jason Bishop, filed the complaint in Miami-Dade Circuit Court. The Bishops allege Bilbao de la Vega negligently turned her husband’s Cadillac Escalade into a crosswalk and struck their son, who was riding an electric scooter. Bishop’s family also accused Daniel de la Vega of negligent entrustment of the vehicle.
Bilbao de la Vega was charged with failure to use due care, a traffic violation, and a second degree misdemeanor of driving with an expired license, court filings show. She pleaded no contest to the charges, and she received probation in January. A Miami-Dade judge ordered her to pay the maximum fine of $1,000, plus court costs, and serve 500 hours of community service.
The family and the couple reached a private settlement, and the civil case was dismissed this month.
Mystery smear campaign targets Michael Stern
An unknown Internet hater is out to get Michael Stern. In April, Stern and his JDS Development Group sued a John Doe in Miami-Dade Circuit Court, alleging an anonymous rival orchestrated an online smear campaign accusing Stern of fraud.
The operator behind JDSpulse.com and affiliated social media accounts allegedly claimed Stern has a “documented criminal history” and that his business is “plagued by unethical practices, financial misconduct, and fraudulent dealings.” Stern flatly denied the allegations, and is suing for unspecified damages in his defamation complaint.
Though the website has since gone dark, the suit says the posts triggered “unpleasant conversations” with investors and seeks to unmask the perpetrator to recover the damages. The complaint is pending.
Elliman clashes with Eichner’s Continuum
Douglas Elliman had a hard time breaking up with developer Ian Bruce Eichner’s Continuum Company.
In January, the brokerage sued a Continuum affiliate that took over sales for a 32-story, 198-unit condominium Eichner is building in North Bay Village.
The lawsuit, filed in Miami-Dade Circuit Court, accused Continuum of poaching agents Ruben Alvarez and Karla De La Torre after the developer fired Elliman as the exclusive brokerage for the planned Continuum Club & Residences.
Continuum breached its contract with Elliman by hiring Alvarz and De La Torre without Elliman’s consent, triggering a $200,000-per-breach clawback, the lawsuit alleged. The brokerage is seeking $400,000 in damages under a marketing agreement.
Elliman and Continuum reached a private settlement that still needs a judge’s signoff, a recent court filing states.
Justin Rundle versus Canero Group
A bitter partnership fallout led investor Justin Rundle, son of Miami-Dade State Attorney Katherine Fernandez Rundle, to fire off a legal torpedo against Canero Group principals Jose Canero Sr. and his son Jose Jr., nearly wrecking the growing development firm’s project pipeline.
Rundle sued the Caneros and their firm in Miami-Dade Circuit Court in May, alleging his business partners engaged in a scheme in which they allegedly used project funds to pay their company’s expenses without authorization from Rundle and other investors, while also unnecessarily delaying the projects.
Canero Group began as a luxury home builder but expanded into multifamily and townhome development in recent years. Rundle began investing in 2023 and brought on other investors to fund six Canero Group projects, the complaint states. He sought damages in excess of $3 million.
The Caneros denied any wrongdoing and accused Rundle of violating Florida bar conflict of interest rules involving lawyers getting into business with clients. Rundle reached a settlement with the Caneros in October. He walked back his fraud allegations after an independent third-party accountant found no fraud or misappropriation of funds, according to a Rundle spokesperson.
Prive Group flips the script
Usually, investors are the ones lining up to accuse South Florida developers of bait-and-switch tactics. But a January lawsuit by Prive Group and CEO Javier Rabinovich aims to flip the antagonists in that familiar script.
Their lawsuit in Miami-Dade Circuit Court seeks $20 million in damages from six Peruvian investors and their firm YVY Project Management, claiming they attempted a hostile takeover of an Aventura condo site and a Fort Lauderdale apartment project after Prive secured zoning approvals.
Prive, known for an Aventura office condo and the Uptown Biscayne mixed-use project, also slapped lis pendens on the two development sites to block any sale while the dispute plays out.
However, the case was placed on inactive status in April, court records show.
Brickell condo in legal seige
Fed-up owners of a condo complex at 1060 Brickell voted late last year to oust board president Jacob Kassel, spawning a legal tussle that’s raged since January.
Following a $21 million special assessment and the elimination of electronic voting, unit owner Kimberly Spahr and fellow residents sued in Miami-Dade Circuit Court, alleging the Kassel-led condo association improperly canceled the election on the pretext of too few candidates. The complaint alleges the board wrongly disqualified Spahr over a “monetary obligation” rather than an unpaid assessment, contrary to state law.
Backed financially and politically by roughly 180 owners, about a third of the two-tower development’s ownership, the plaintiffs are asking a judge to restore the ballot box — and strip Kassel of power. The case is pending.
Supermodel fights Fisher Island bigwigs
Supermodel Karolina Kurkova and her husband, actor and broker Archie Drury, sued the Fisher Island Club in February, accusing it of illegal strong-arming and intimidation that forced them off one of the country’s richest ZIP codes.
The complaint alleges the board has been operating under invalid bylaws. Two directors — Douglas Elliman chairman David Chene and fellow Elliman board member Mark Zeitchick — used their positions to steer lucrative work to their brokerage on Fisher Island’s last big development site, the lawsuit claims. Kurkova and Drury, recently expelled from the club, allege the board smeared Drury, leveraged threats and bent governance rules to sideline the couple while positioning Elliman as the lead broker on remaining prime land.
Fisher Island Club dismissed the allegations as the gripes of “disgruntled former members.”
The complaint is pending.
Palm Beach Shores developers dragged over $4.9M
The courtroom battles for the developers of a troubled Palm Beach Shores project keep piling up. In January, investor Daniel Perla sued the team behind a planned three-building, 15-unit condominium complex in Palm Beach Circuit Court.
Perla alleges developers Marc Shulman, Anthony Shafer and a web of entities stiffed him on $4.9 million in loans that were supposed to help fund the project’s construction. The complaint states Perla extended two high-interest loans — a $2 million note at 15 percent in 2021 and another $2 million at 10 percent in 2022. The complaint is pending.
Alden Global accused of a multi-million shortchange
Joseph Miller, a longtime lieutenant to Alden Global Capital boss Randall Smith, accused his ex-employer in January of stiffing him out of millions of dollars.
Miller sued Alden’s real estate arm Twenty Lake Holdings and an affiliate of hotel developer Blue Suede Hospitality in Delaware court over what he calls a lowball buyout on a national portfolio of hotels and warehouses.
Miller alleges he spent more than a decade growing the real estate business, earning a 10 percent stake in Twenty Lake and a 3 percent stake in two Blue Suede hotels in Miami Beach and Charlottesville. After he split with Smith and Alden Global, Miller was offered $3.5 million for his equity and $2 million for his hotel interests, which Miller alleged is “not remotely credible or appropriate.”
The complaint pegs the book value of his Twenty Lake stake at more than $15 million based on an August valuation of 88 properties. Miller also said third-party appraisals could push his entitlement north of $26 million, setting up a high-stakes valuation fight.