SAN JUAN, Puerto Rico - Nearly a decade before Puerto Rico's disgraced Gov. Ricardo Rosselló ran for office, the ambitious and telegenic young man and his closest friends made no secret of his aspirations to move back to the palatial governor's mansion where he grew up as the scion of money and privilege.
"Ricky's friends regularly joked about the positions they would hold in his future administration," said Yosem Companys, a onetime mentor to Rosselló. "All he ever really wanted to do was become governor."
No matter who replaces Rosselló until the end of his term in January 2021, the collapse of his once-promising career in politics -- following in the footsteps of his father, Pedro, the former governor -- will leave an indelible stain on the legacy of one of the island's most powerful political dynasties.
"He is going to be the most disgraced governor in the history of Puerto Rico," Companys said of the younger Rosselló. "And he's basically dragged his father down with him. The name will now be persona non grata in Puerto Rico."
Rosselló's press office did not immediately respond to multiple requests for comment.
Hurricane Maria may have set downfall in motion
The embattled Rosselló, 40, stepped down Friday afternoon after weeks of protests but the island's Senate confirmation of his next secretary of state and eventual successor, Pedro Pierluisi, is mired in uncertainty, intraparty feuding and a possible court fight.
Still, Pierluisi was sworn in as Rosselló's likely successor on Friday, with the Senate set to vote on the appointment next week.
The political firestorm that preceded Rosselló's historic resignation saw its embers in a series of scandals that included the recent disclosure of crude, sexist and homophobic chat messages between the governor and members of his inner circle.
Last month, days before the leaked chats, FBI agents arrested two ranking Rosselló officials, accusing them of directing contracts worth millions to politically-connected firms. For many, the moment harkened to the scandals that plagued the second term of his father, Pedro Rosselló, a Yale-educated and Harvard-trained doctor who served as governor in the 1990s.
Indeed, long before Puerto Ricans took to the streets for nearly two weeks in July to demand that Rosselló step down, generations had lived through monumental levels of corruption and mismanagement at the hands of a disconnected political class.
A prolonged economic recession and Puerto Rico's debt crisis in recent years resulted in shuttered schools, cuts in government service, layoffs and university tuition hikes. Three years ago, the US Congress created a board to oversee the US territory's finances -- a body that also drew the ire of the anti-Rosselló protesters.
But the eventual downfall of his administration may have been set in motion by Hurricane Maria in 2017. The devastating storm made landfall less than nine months after Rosselló returned as governor to the 16th-century mansion known as La Fortaleza.
"The hurricane put him in a situation where he was definitely in over his head," said Companys, a Half Moon Bay, California, resident and president of the Silicon Valley firm Techlantis.
Chats reveal arrogance and insolence of the political elite
Hurricane Maria decimated the island's antiquated power grid. Many residents were left in the dark for months. The administration ignored advice from attorneys before inking a controversial $300 million contract with Whitefish Energy, a small Montana-based firm that only employed two people at the time Maria hit.
There were widespread problems with the distribution of food, water and other vital supplies to those who needed it most. And it wasn't until nearly a year after the storm that the Rosselló administration finally admitted that the storm left several thousand people dead -- not the dozens that had been the official line.
"It was evident after Maria that Rosselló didn't know what he was doing," said Mario Negron Portillo, a political expert and retired University of Puerto Rico professor. "Everything went downhill after Maria."
Still, the chats that surfaced a year and half after the storm -- an affair dubbed "Rickyleaks" -- proved his final undoing.
For a huge swath of the populace -- a cross-section of various generations and people of different political stripes -- the messages exposed the arrogance and insolence of a political elite long divorced from the struggles of ordinary people.
In the chats, Rosselló and his inner circle offended nearly every one of the island's 3 million residents. They took aim at women, gay people, overweight people, a revered independence movement leader who died of cancer, and the thousands of hurricane victims.
"There were a lot of jokes over the years about Ricardo Rosselló being this entitled kid who had all the privileges and never had to work or face any consequences for anything," said Mayra Velez Serrano, a professor of political science at the University of Puerto Rico at Rio Piedras.
"The chats basically confirmed that. He was still very immature. He still talked like he didn't realize the responsibility he had."
Pedro Rosselló discouraged son from pursuing politics, former mentor says
Rosselló's first foray into politics came in the early 2000s. Companys, who was an adviser on Latino issues for the campaign of Democratic presidential candidate Wesley Clark, would become his mentor. Pedro Rosselló had done the same for a younger Companys, who now got the younger Rosselló campaign work in Arizona.
"His job was basically licking envelopes," Companys recalled. "I told Pedro, 'Look, I'm going to put him to lick envelopes. He said, 'Good. He needs to learn responsibility.'"
Companys remembered a phone call in which Pedro Rosselló said he had encouraged the youngest of his three sons to stay out of politics.
"Pedro had really soured on politics," he said. "He would always say, 'I don't want my son in politics because it's a dirty business. I don't want him to get hurt.'"
Pedro Rosselló did not immediately respond to requests for comment.
Over the years, the younger Rosselló worked on two unsuccessful bids at the island's top office by his father, who had already governed from 1993 to 2000. At the time of his first marriage outside of Detroit in 2008, Rosselló and his friends talked about the governorship and the positions they would hold as members of the pro-statehood New Progressive Party, according to Companys.
"He tended to be surrounded by 'yes' people and if anybody criticized him, he would kick them out of his circle," Companys recalled. "He started liking the fact that people tried to ingratiate themselves with him because they found him to be important."
Like his father in his prime, Rosselló sought to ride his boyish good looks and academic credentials to La Fortaleza. He played tennis like his dad, a former tennis champion on the island. He graduated from MIT with degrees in biomedical engineering and economics before earning a doctorate at the University of Michigan.
"Ricardo was able to take advantage of his last name," Negron Portillo said. "People still remembered his father fondly."
Still, the elder Rosselló, at least initially, was apprehensive about his son's political ambitions, according to Companys.
"The way that his parents described it ... was that he was the most brilliant person in the family but he was an absent-minded professor like Dr. Emmett Brown in 'Back to the Future,'" he said.
Rosselló downplayed his lack of political and work experience, Companys said.
"He would say, 'I really don't think I need it. I think I can get elected without it," Companys recalled.
Rosselló ran for governor in 2016. He took office in January 2017 alongside a tight circle of loyal advisers who, like him, possessed little or no political experience, according to Negron Portillo, Campanys and others.
"Ricardo and his friends may have let the boat come down," said Alvaro Cifuentes, who was part of Pedro Rosselló's cabinet during his first term. "I mean, you need to have a fortitude of historic proportion when you're the leader of any state or any nation. It should not be taken lightly."
His father's administration credited for big projects but plagued by corruption
Pedro Rosselló, 75, burst into electoral politics in the early 1990s. He was a longtime pediatric surgeon and, like the son who would follow his footsteps decades later, a relative political novice.
But he had wide appeal among pro-statehood, commonwealth and independence supporters -- with promises to combat crime, improve education, increase health services and slash taxes.
"I didn't know Pedro before" the campaign, said Cifuentes, who at the time was a managing partner in a law firm on the island. "He was recommended to me as a pediatric surgeon because my son needed a small surgery. I was enchanted by the demeanor and the care that he had toward my young son. How he gave us so much comfort."
Cifuentes became his campaign manager. The morning after the election, Rosselló offered him the post of secretary of government.
"I said, 'Pedro, what's that?'" Cifuentes recalled. "And his answer was, 'I don't know but it has to be my alter ego and someone that I can trust.'"
The elder Rosselló would become the architect of large-scale projects like an urban metro rail system, a convention center complex and a sprawling coliseum that would eventually saddle the island in debt.
"We had a saying, 'We don't talk. We walk,'" Cifuentes said. "We were very good at implementing. And that all came from Pedro Rosselló, the doctor."
Rosselló dispatched the National Guard to crime-ridden housing projects. He slashed the bloated government workforce. He offered private health insurance to the poor.
But his second term was marked by corruption scandals involving dozens of ranking members of his administration and party, including his top personal assistant, a former education secretary and a former House speaker. In the summer of 2000, a federal prosecutor was quoted as saying, "In Puerto Rico, corruption has a first and last name -- the New Progressive Party."
"On one hand, Pedro Rosselló was remembered for the big projects and the good economy under his leadership and, on the other hand, people remember him because of the corruption of the times," Negron Portillo said.
Pedro Rosselló was never charged or accused of any crimes. Over the years, he and supporters said the prosecutions were an attempt by political opponents to discredit the pro-statehood movement.
Cifuentes said the scandals were the work of "the usual suspects" who have long infected island politics with patronage and cronyism.
Pedro Rosselló, who served as governor until the end of 2000, was defeated when he tried to return to the governor's seat in 2004.
His son, Ricardo, isolated in La Fortaleza after the resignations of many of his top aides and facing increasing protests and clashes in the streets, announced on July 24 that would step down.
"Pedro Rosselló, as an elected official from day one, never lived by the mantra of being a legend in his own mind," Cifuentes said.
"But over the past two and half years, when you have a government where individuals believe they're legends in their own minds, that always spells trouble."
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