Marco Rubio, his American Dream backstory, and how his sister's husband was convicted of major drug crimes

On 16 December, 1987, a teenager named Marco Rubio arrived home from school in West Miami to find his mother in anguish.

Earlier that day, federal drug agents raided a house a few miles away that his brother-in-law, Orlando Cicilia, shared with Rubio's older sister, Barbara. Cicilia, a large, sturdily built Cuban immigrant, had played an intimate role in Rubio's early life. But as the future Senator from Florida was finishing high school and preparing to go to college, his brother-in-law's illicit career as a cocaine dealer was exposed in a major trial. Cicilia was sentenced to a lengthy prison term in one of the biggest drug cases of Miami's baroque cocaine-cowboys era.

Rubio, 16 at the time, does not appear to mention the ordeal as he runs for President, casting his family's Cuban American immigrant story as the embodiment of the American Dream.

There is no suggestion that Rubio or his parents were aware of Cicilia's drug dealing, and Rubio's sister was not suspected of any crime. But a deep look at those turbulent years – drawing on previously unreported Drug Enforcement Administration field reports and grand jury testimony, interviews with federal task force agents and the senator's writings – reveals that Cicilia was a central figure in the smuggling operation at the same time that he was integrated in the life of the Rubio family.

While the case was widely covered at the time, many details of Cicilia's top-level role in the smuggling operation have not been previously reported, in part because they were stored in court files that were antiquated and difficult to access, as well as in remote archives. Cicilia served as the "front man" in the drug ring headed by Mario Tabraue, a kingpin who ran an exotic animals business and kept spotted leopards in the walled grounds of his mansion, according to interviews and court records. Cicilia looked and sounded the part, wearing paisley suits and rakishly calling cocaine "a pretty thing", according to court records.

The depiction of Cicilia's criminal activities that emerges in interviews and records goes well beyond the description offered by Rubio in his 2012 memoir. In the book, An American Son, Rubio refers vaguely to Cicilia's involvement "in a criminal enterprise" without mentioning the scope of the drug ring. Rubio, who had moved with his parents back to Miami from Las Vegas more than two years before the arrest, writes poignantly about the arrest's effect on his sister and parents. But he plays down its impact on him personally, noting that his "family's troubles didn't diminish my enthusiasm for the upcoming football season".

Rubio declined to be interviewed. His spokesman, Todd Harris, said Rubio "was just 16 at the time of the arrest and views this as a private family matter involving events that occurred almost 30 years ago". Initially, Rubio declined to answer written questions about whether Orlando Cicilia ever provided financial support to him or his family, or if he took any steps to help secure the early release of his brother-in-law from federal prison. Harris sent an email after this story was published online saying that Rubio did not help Cicilia win early release. Harris did not address the financial support question.

Orlando and Barbara Cicilia remained married throughout his 12-year prison term. Cicilia, now 58, and his wife live in Rubio's childhood home with the senator's mother, Oriales Rubio, whom the Republican candidate mentions frequently on the campaign trail. Property records show that Rubio's parents added the names of Orlando and Barbara Cicilia to the home's deed in 2002, two years after Cicilia's release.

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When Rubio's Senate campaign was looking for office space, it was Cicilia, now a real estate agent, who helped to find a location, according to a friend. Cicilia has had no further troubles with the law, according to court records. Rubio, now 44, is close to Cicilia's sons, Daniel and Orlando, the latter nicknamed "Landy". They call Rubio "Tony," an Americanised version of his middle name, Antonio. Rubio-affiliated PACs and his campaigns, including his presidential operation, have paid more than $130,000 to his nephews over the past decade, the bulk going to Landy Cicilia's video and consulting companies. The Cicilia sons did not respond to requests for comment.

On the night of Rubio's 2010 Senate victory it was Landy Cicilia who drove Rubio to the elegant Biltmore Hotel in Coral Gables, Florida, for his celebration. On stage that night, with confetti cascading down, music blaring and an audience looking on, a graying man stood behind Rubio: Orlando Cicilia.

Orlando Cicilia was born in Cuba into a family of real guajiros – Cuban country folk. He appears to have arrived in the United States at age 15 in 1972 –16 years after Marco Rubio's parents and maternal grandfather, according to Social Security Administration records.

Cicilia began dating Barbara Rubio in the 1970s. As the years went on, the jovial Cicilia showed a knack for awakening nostalgic emotions in the Rubio family, the senator would later recall. His ways were the ways of the island, and being around him and his family could transport Marco Rubio's father, Mario Rubio, back to the place of his birth.

The families shared a common heritage. Rubio's grandfather was born in the small rural village of Jicotea in north-central Cuba. Rubio, who was born in the US, was just a boy when Cicilia entered his family's life. One Christmas Eve when he was a small child, he got out of bed and found Cicilia assembling a bicycle with his father in the living room of their home.

"You would have thought I'd walked in on two burglars," Rubio wrote in his memoir. "After a frantic attempt to cover up the evidence, my father and Orlando explained they had both been using the bathroom when Santa Claus had arrived and delivered our presents. It sounded plausible to me, and I went back to bed happy that Santa had made it to our house."

The Miami of Rubio's youth was fast becoming the cocaine capital of the United States. And the dealers who made millions selling it were becoming more brazen, and more violent.

"There were shootings at intersections. There were shootings in swimming pools. There were bodies everywhere," said Sam Rabin, a prosecutor in charge of a drug-homicide task force that investigated the Tabraue ring. "It was the Wild West." In 1979, when Rubio was eight, his father announced that they would leave the city for Las Vegas. Rubio's sister, who would turn 20 that year, didn't want to go. She wanted to stay in Miami with Cicilia. "Her decision terribly upset my parents," Rubio wrote. "If Orlando truly loved her, my mother argued, he would marry her now or follow us to Las Vegas. But more than her relationship with Orlando kept my sister in Miami. All her friends lived there. It was her home." The family left without her.

In Las Vegas, Rubio and his mother joined the Mormon Church. His parents had hoped Las Vegas would provide better job opportunities for Rubio's bartender father at a time when the hospitality business in Miami was sagging. But in Las Vegas, they struggled.

But the family in Miami was prospering. Barbara had married Cicilia, and they'd bought a house with an acre of land in a suburban area west of Miami. In 1983, when Rubio was 12, the couple hosted the Rubios for a traditional Cuban Nochebuena – Christmas Eve. Cicilia's family joined them, slaughtering a pig and roasting it in a pit covered with palm fronds.

"It had been a long time since I'd seen my parents so happy," Rubio wrote. "My father had felt transported to his childhood... my grandfather was as close to our family's rural Cuban heritage as he had been since his boyhood." The trip, Rubio wrote, "reawakened my affection for the city and the Cuban culture so prevalent there". Decades later, the Christmas at Cicilia's remained Rubio's "fondest childhood memory".

That year was pivotal in the life of Rubio's brother-in-law. In 1983, Cicilia joined the cocaine-smuggling operation led by Tabraue, according to prosecutors, investigators and witnesses. At that point, Tabraue had a booming drug business, according to law enforcement officials who tracked him. Tabraue's drug ring had been populated by thugs known for their ruthlessness; some carried pistols in briefcases. Prosecutors believed that a member of Tabraue's crew had killed Larry Nash, an undercover informant for what was then the Bureau of Alcohol, Tobacco and Firearms, in 1980 and disposed of his body by dismembering it with a circular saw and burning it in a horse trough filled with charcoal. Nash's body was never found.

What began as a marijuana-import operation in the late 1970s had blossomed into the far more lucrative business of distributing kilos of cocaine smuggled into South Florida from Colombia. During operations from 1976 to 1986, the ring moved half-a-million pounds of marijuana and 200 pounds of cocaine worth an estimated $75m. "It was a very large operation," said Delbert Woodburn, a Miami-Dade narcotics detective who investigated Tabraue in the late 1970s and early 1980s. "Planes from Colombia were coming into the Bahamas and the Keys, landing at small airports, dropping drugs into the Everglades."

Cicilia became the "front man," insulating Tabraue by handing over drugs to buyers and coordinating shipments, according to interviews, DEA field reports and grand jury testimony obtained by The Washington Post.

As the business flourished, Cicilia took on the appearance of the quintessential Miami underworld hotshot, donning sunglasses and wearing his paisley suit sleeves rolled up. It was as if he'd walked off a Miami Vice TV set, Larry A Loveless, the lead DEA agent in the investigation, said in a recent interview.

Cicilia worked out of Tabraue's business in southwest Miami, Zoological Imports Unlimited, which agents called "the pet store".

While Cicilia was flourishing, the Rubio family was going through a difficult period. Finances were a worry, and his father would eventually lose time at work because his union went on strike. His parents, a bartender and a hotel maid, worried that their youngest children, Marco and Veronica, would not go to college. In 1985, his father made a big decision. He bought a modest home in West Miami, and the family moved back. At first, Rubio protested, preferring to stay in Las Vegas, but he soon warmed to returning to "the exciting city I saw on Miami Vice", he wrote.

Amid the upheaval in Rubio's life, one constant was his love of the Dolphins football team. But he didn't have the money for tickets. He turned to his sister and brother-in-law for help. The couple agreed to pay Rubio $10 a week for each of their seven Samoyed dogs he washed. He made enough to buy tickets for all eight Dolphins home games, Rubio wrote.

That same house would soon be under surveillance by federal agents. The suspicions of federal investigators about Tabraue's possible involvement in the disappearance of the informant had lent a note of intensity to their surveillance of the kingpin and, ultimately, Cicilia.

Detectives had noticed a man behind the wheel of a Chevy Blazer that was appearing frequently among the stream of Ferraris, Maseratis and Jaguars that flowed to and from the kingpin's pet store.

At first, the agents referred to the man in their reports as "Orlando LNU" (last name unknown). After following him around, they learned that his name was Orlando Cicilia.

Cicilia handled the inventory for Tabraue, coordinated shipments around the country and collected the money, according to DEA field reports and court records. Sometimes he would stash the cocaine at his home.

DEA agents installed a listening device at the pet store and tracked calls made to and from Cicilia's home phone. Their informant wore a wire during his conversations with Cicilia and Tabraue.

As the DEA agents recorded the conversations, one thing became clear: Cicilia was the go-to man for the operation's cocaine transactions, whether they involved a few ounces or multiple kilos. In 101 pages of DEA field reports and sworn statements obtained by The Washington Post, Cicilia is named 147 times.

Cicilia used code words for cocaine buys: "little birds" for ounces, "big birds" for kilos. He boasted that the cocaine offered by the Tabraue ring was some of the best on the street.

Federal agents and Miami police gathered before sunrise on 16 December, 1987. In the early morning, nine days before Christmas, they fanned across Miami. Cicilia was arrested at his house. Tabraue was arrested at his compound. Inside the mansion were four safes – including one in a child's room – an Uzi and a MAC-10 submachine pistol. During the frenzy of the raid, the kingpin's wife threw a $50,000 bundle of cash out of a window. It hit a law enforcement agent in the head.

When Marco Rubio got home from school that afternoon, the pain caused by that morning's events was etched on his mother's face. "It was a look you expect to see when someone has been told they or someone they love is dying," Rubio wrote in his memoir.

The case went to trial 11 months later in an ornate downtown Miami courtroom packed with local lawyers who came to gawk at the legal firepower. Cicilia was represented by a court-appointed attorney, but his co-defendants brought in star attorneys, including Roy Black, one of the nation's most prominent criminal lawyers, and Richard Sharpstein, a brilliant legal mind and showy performer who entertained the jury by imitating the rumpled TV detective Columbo.

Jurors heard evidence about drug deals Cicilia was involved in during 1986, but prosecutors and witnesses said he had joined Tabraue's gang in 1983. Cicilia's attorney tried to persuade jurors that he was not engaged in the drug business. They didn't buy it. On 6 February 1989, the jury convicted Tabraue, Cicilia and five other men. Tabraue got 100 years in prison but would be released early in 2003 after serving 14 years. Cicilia received 35 years, the second-longest sentence, and the jury found him responsible for $15m in drug sales. The money has never been found.

While the case played out, Rubio saw the corrosive effects of crime up close. His sister yearned for company. Once, she invited him for pizza and a movie, but he turned her down because he was busy socialising with high school friends – a decision he would later regret. "Barbara was lonely, and I avoided her," Rubio wrote. The government had seized the home Barbara owned with Cicilia, and she had to move into a garage apartment at the Rubio family home.

Four days after the home seizure, Rubio left for Tarkio College. The tiny Missouri school had given him a scholarship to play football. It wasn't long before he was the one feeling miserable; he was having a hard time adjusting to life in the small college town.

On a trip to Miami, he met his newborn nephew, Daniel. His mother reminded him about "how lonely and difficult" Barbara's life had been since Cicilia's arrest. Three years earlier, when the couple's first child had been born, his sister's hospital room "had been crowded with flowersand friends," Rubio recalled in his memoir. When she gave birth to her second son, the only flowers were sent by her parents; they were also her only visitors.

Rubio left Tarkio after one year, transferring first to a community college and then to the University of Florida, where he earned an undergraduate degree before going on to the University of Miami law school.

In the coming years, while his brother-in-law served time at a low-security federal correctional institution in Ashland, Kentucky, Rubio launched one of modern Florida history's most successful and rapid political careers.

Rubio's reputation as a young man with great promise was sealed in January 2000 when he won a special election to serve in the Florida House of Representatives after having served on the city commission in West Miami. That November, he was re-elected for a full term.

Four days after the election, Inmate 12101-016 walked out of federal custody. Orlando Cicilia was a free man.

Alice Crites contributed to this report

© Washington Post​