Alex Díaz de la Portilla’s political career is marked by both power and conflict

For much of his 30-year career in politics, Alex Díaz de la Portilla has swung from risk and rejection to redemption.

Arrested Thursday on charges of money laundering, unlawful compensation and other wrongdoing relating to campaign finance expenses, the allegations are not the first time the veteran politician has faced campaign finance and breach of ethics violations, but they may now be the most serious.

Díaz de la Portilla, 58, is known locally as D.L.P. The second son of Cuban exiles Miguel Ángel Díaz Pardo and Fabiola Pura de la Portilla García, he is arguably the most prominent Miami member of the family’s Cuban-American political dynasty.

He served six years in the Florida House and eight in the Florida Senate, rising into leadership posts in both chambers. He commanded powerful committees and Republican party posts that brought him clout and access to millions in campaign donations. Between 1994 and 2004, he never lost an election.

In his early career, Díaz de la Portilla earned the reputation as “the bad boy of the Florida Legislature.” He was known as a late-night partier, branded a traitor by fellow Republicans for trying to install former Rep. Luis Rojas of Hialeah as the next House speaker over Orlando Rep. Dan Webster, missed more votes than any other legislator, and was censured by the Miami-Dade Republican Party for crossing party leaders.

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His older and younger brothers, Miguel and Renier, have also been fixtures in Miami politics and government, with Miguel having served in the Florida Senate and on the Miami-Dade County Commission, and Renier having served on the Miami-Dade County School board and succeeding Alex for one term in the state House. Born and raised in Little Havana, their paternal great-grandfather served in the Cuban Senate. Their maternal great-grandfather served as Cuban Minister of Justice.

Since Alex Díaz de la Portilla was first elected to the state House in 1994, he has positioned himself near the center of power in every government post he has held. But his handling of the role, and the frequent conflicts between his personal and business endeavors, have drawn a litany of legal and ethical challenges, including previous violations of Florida campaign finance laws.

A campaign finance fine 30 years ago

In 1995, the Florida Elections Commission fined him $500 for filing his 1992 campaign finance reports more than a year late. And in 2007, Díaz de la Portilla agreed to pay nearly $9,000 in fines after successfully challenging $311,000 in fines sought by the Florida Elections Commission.

The commission had mounted what was then a record fine after accusing the then-state representative of willfully ignoring campaign finance law and misleading the public about how much money he had raised in a 2000-special election against opponent state Rep. Carlos Valdes.

State ethics officials accused Díaz de la Portilla of not reporting personal loans and contributions worth more than $150,000. Some of the money had been used for last-minute attack ads against Valdes. After the commission agreed to whittle down the fine to $17,000, Díaz de la Portilla took his case to court. He told the judge he couldn’t afford to pay the penalty, saying his only source of income was the roughly $30,000 he made as an elected official. The judge referred to his lifestyle and said he didn’t believe him.

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Díaz de la Portilla was first elected to the House in 1994 in a West Miami-Dade district, after two unsuccessful attempts to win the seat. In that campaign, he had to overcome criticism for several arrests in the 1980s, including allegations that he threatened his girlfriend in 1983, and another that he obstructed a police officer after a 1987 traffic stop. He was not found guilty in either of them, but he has a long law enforcement record.

In his 20s and early 30s, Díaz de la Portilla received more than 23 traffic tickets over 12 years, and his license was suspended 16 times — mostly for missing court dates. At the time, Díaz de la Portilla blamed the arrests on “youthful indiscretions.”

“I was just a kid,’’ he told the Miami Herald in 2003. “I had a big mouth.” He attributed his failure to go to court on his travels working for the family’s mattress business, De Mattress.

Becoming a power player in Tallahassee

But after six years in the state House and successful election to the state Senate in 2000, Díaz de la Portilla had emerged from his role with his family’s business to be a political consultant by trade. In 2002, Jacksonville Republican Jim King, a popular and well-respected Senate president, named the new senator his president pro tempore, the second-ranking position in the Senate.

King said at the time that he was taking his chance on Díaz de la Portilla, whom he called “a born-again senator,” because he was “early to meetings, does his homework, is a vital part of the inner circle of leadership and does my bidding.”

Díaz de la Portilla’s legacy included shepherding former Gov. Jeb Bush’s education reform plan through the House, working to legalize slot machines at dog and horse tracks in Florida, and helping to resurrect the foundering campaigns of more than one Senate colleague.

But in recent years, conflicts in his personal life also got the former senator in trouble.

In 2010, a Leon County Circuit Court judge issued a restraining order to keep him away from his estranged wife, Claudia Davant, and the Governors Club, a popular private club in Tallahassee. Davant said in court papers that she had been stalked and threatened and was in “eminent fear for my life.”

In her affidavit, Davant claimed that Díaz de la Portilla or one of his associates tried to break into her office and had her home bugged and computer and phone hacked. She also said that she was followed by one of Díaz de la Portilla’s associates. She complained her ex-husband had an “explosive” temper.

A year later, another Leon County Circuit Court judge issued a warrant for his arrest, after Díaz de la Portilla refused to turn over a Weimaraner dog to his ex-wife as part of the divorce case.

Entanglements with the Gimenez family

In 2012, Díaz de la Portilla and a guest were arrested at a Boston hotel after ignoring orders from security guards who told them to stop smoking cigarettes in their room and then told them to leave. They were charged with misdemeanor trespassing, but the charges were dismissed before arraignment.

The guest in the room was Tania Cruz-Gimenez, the daughter-in-law of then Miami-Dade County Mayor Carlos A. Gimenez. now a U.S. congressman from Miami. It’s possible that circumstance contributed to what was Díaz de la Portilla’s highest profile dust-up until Thursday’s arrest.

Ten years later, in a February 2022 encounter at Morton’s Steakhouse in Coral Gables, Carlos J. Gimenez, son of former mayor and current congressman Carlos Gimenez, slapped Díaz de la Portilla on the back of the head and swore at him.

Díaz de la Portilla’s security detail, a detective from the Miami Police Department, intervened and the younger Gimenez was arrested and spent a night in jail. The charges were dropped.

After a nine-year hiatus after leaving the Senate because of term limits, and three unsuccessful campaigns, Díaz de la Portilla returned to elected office on the Miami commission.

In 2012, he lost a run for state House. In 2017, he lost the Republican primary for a Florida Senate district, a seat left open after former Sen. Frank Artiles resigned. And in 2018, he failed to make the runoff in the race to fill an empty Miami-Dade County Commission seat.

In April 2020, Díaz de la Portilla was elected to the Miami City Commission, representing Flagami, Allapattah and parts of Little Havana in District 1. His city commission colleagues voted to make him chairman of the Omni Community Redevelopment Agency, a powerful board charged with providing affordable housing and development in the city’s blighted areas.

He soon urged the CRA to hire Jenny Nillo, a former aide to his brother Miguel, as a “redevelopment project development specialist,” at a salary of $45,000 a year. She had been sentenced to 36 months in federal prison for mortgage fraud and was serving probation.

But after Nillo was found rarely showing up for work and using her city-issued automobile to run personal errands for Díaz de la Portilla, the CRA fired her and voted out Díaz de la Portilla as chair.

By 2022, Díaz de la Portilla had another redemption. He reclaimed control of the powerful board, and his colleagues named him chair again.

Mary Ellen Klas can be reached at meklas@miamiherald.com and @MaryEllenKlas