Sean Penn makes a cameo in Miami’s elections, and the mayor threatens to sue

Miami Mayor Tomás Regalado says he plans to sue long-time nemesis Joe Carollo after the latter mailed out political ads that juxtapose a chummy picture of the mayor and actor Sean Penn with photos of Penn greeting leftist Latin American leaders.

“Sean Penn, a known defender of Castroism and Chavism, with his favorite dictators, Tomás Regalado and his son,” states the mailer, created and distributed by Carollo’s Miami First political committee.

The ad features a photo that Regalado and son Jose Regalado took with Penn on Dec. 28, 2010 when they were taken up to Penn’s box suite at the AmericanAirlines Arena and introduced by a Miami Heat employee while attending a game against the New York Knicks. Next to the photo are others of Penn taken over the years with Cuban dictator Raúl Castro, Venezuelan president Nicolás Maduro, Maduro’s late predecessor Hugo Chávez, and Bolivia’s Evo Morales.

Carollo is running against Regalado’s oldest son, Tomas N. “Tommy” Regalado, and five others for Miami’s District 3 Commission seat, which represents a largely Hispanic voting base, nearly two-thirds of whom are Republican or lack party affiliation. He says he distributed the political hit piece in order to reveal the Regalado family’s duplicitous nature.

“He’ll say one thing to your face and then do something else behind your back,” Carollo said in an interview. “That’s been his whole history.”

Regalado, who came to Miami from Cuba as a child on a Pedro Pan flight, is the son of a political prisoner. He has frequently criticized leftist regimes, and said he would sue to block a Cuban consulate in Miami after the Obama administration opened up diplomatic relations with Cuba. Penn, on the other hand, has praised Chavez, interviewed Castro, and played the role of diplomat in Bolivia.

Regalado, who told blogger Elaine De Valle Sunday that he was “distracted” and didn’t know who Penn was when they took the photo, told the Miami Herald that Carollo went too far.

“When I finish my term I’m going to find an attorney and I’m going to sue him,” Regalado said. “I am very offended. My father was a political prisoner. He died here because he got sick in jail. [Carollo] can call me anything. But calling me a communist, calling my family a communist, I am very offended.”

Carollo, however, says he’s never called Regalado a Communist, but rather told voters that the family has accepted political donations into a political committee from Chavistas.

“What I’ve sent has been hard-hitting. But it’s been factual,” said Carollo, who blames the Regalado for attacks sent recently against him by a Tallahassee-based political committee. “I don’t believe Tomás Regalado is a communist. I believe Tomás Regalado is a opportunist.”

This story was originally published October 24, 2017 at 12:38 PM with the headline "Sean Penn makes a cameo in Miami’s elections, and the mayor threatens to sue."