News of a misdemeanor arrest is haunting Republican state Senate candidate Alex Diaz de la Portilla, but the 2012 arrest isn’t the only one on DLP’s criminal record.

On Friday, the Miami Herald published a story detailing the former Miami lawmaker’s arrest in Boston five years ago, after he and a guest ignored hotel security requests to stop smoking cigarettes in their room.

According to a police report, Diaz de la Portilla and Tania Cruz, daughter-in-law of Miami Mayor Carlos Gimenez, were repeatedly told to stop smoking inside their hotel room.

Diaz de la Portilla and Cruz refused.

Boston police then charged Diaz de la Portilla for trespassing. They tried to allow him and Cruz to leave the hotel, but the two were “belligerent” and “intoxicated,” saying they were both lawyers in Miami. After they refused to leave, police took them into custody. 

Mugshots were taken, but no charges were pursued.

The 2012 arrest isn’t the only stain on Diaz de la Portilla’s record. The former Senate majority leader has something of a “bad boy” past. 

In 1983, he found himself in hot water for another misdemeanor, this one for disorderly conduct. The files for the arrest have since been destroyed, but Diaz de la Portilla was charged after threatening his girlfriend.  In 2002 the case was dismissed. 

In 1987, the Miami New Times found Diaz de la Portilla was charged with obstructing a police officer during a traffic stop — a charge he admitted to but shrugged off as “youthful indiscretion.”

“I was just a kid. I had a big mouth,” he said. 

In 2001, Diaz de la Portilla — known in more familiar terms as DLP — faced another round of criminal charges, this time for failing to report campaign contributions.

DLP won that case, but his legal woes didn’t end there.

The former state senator is perhaps most famously known for his messy, high-profile divorce case from 2009 to 2011. 

Like a scene from a movie, the divorce involved stalking charges, a custody battle and fleeing the country to avoid court dates. 

As part of Diaz de la Portilla’s divorce with Claudia Davant, he was supposed to turn over one of the couple’s two dogs, named Elvis and Priscilla, but he never complied. 

Under Florida law, dogs can be classified as property, which typically tends to be divided evenly in divorces. 

Diaz de la Portilla never showed up in court, though, and was slapped with an Order of Contempt and a warrant was put out for his arrest.  He allegedly fled the country with a female companion, heading to the mountains in Italy while the court case raged on.

DLP’s ex-wife Davant also claimed he was stalking her during their divorce proceedings, attempting to break into her office, have her computer hacked, her house bugged and sending someone to beat on the back door of her house late at night “just to cause [her] to be totally in fear.” 

The case ultimately went to the Florida Supreme Court, which sided with Diaz de la Portilla and sent his contempt order back to the trial court. 

Multiple calls to Diaz de la Portilla Saturday night were not immediately returned. 

The news of Diaz de la Portilla’s Boston arrest is just the latest chapter in a brutally ugly Republican primary for Florida’s 40th Senate District, which was vacated in April following the resignation of former state Sen. Frank Artiles, who made racially charged insults about a fellow lawmaker. 

In the GOP primary, Diaz de la Portilla faces former congressional candidate Lorenzo Palomares and Jose Felix “Pepe” Diaz, who resigned from his position in the Florida House of Representatives to make a bid for the Senate seat.

Diaz told the Herald he had “nothing to do” with the news of the 2012 arrest. “I don’t engage in that type of campaigning,” he said.

The final showdown between the three men is July 25, with the special election set for Sept. 27. 

Reach reporter Allison Nielsen by email at [email protected] or follow her on Twitter: @AllisonNielsen

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