Puerto Rico's Governor Ricardo Rossello listens during a press conference on Capitol Hill January 10, 2018 in Washington, DC.
The Puerto Rico Statehood Commission held a news conference "to demand to be seated in the United States House of Representatives and Senate as the legitimate lawmakers of America's 51st state."
 / AFP PHOTO / Brendan SmialowskiBRENDAN SMIALOWSKI/AFP/Getty Images
Puerto Rico governor announces resignation
01:40 - Source: CNN
CNN  — 

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.

Ricardo Rosselló and Yosem Companys at the governor's first wedding outside Detroit in 2008.

“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 reme