"He needs to know that no one in Puerto Rico wants him," a protester told the crowd.
Calls for Rosselló to step down began after nearly 900 pages of leaked chats from a governor's private Telegram Messenger group, obtained by Puerto Rico's Center for Investigative Journalism, were published over the weekend.
Singer and actor Ricky Martin, reggaeton star Bad Bunny and rapper René Pérez Joglar, known as Residente, joined protesters in the American territory's capital.
Bad Bunny held a sign saying "Ricky resign" in Spanish.
"This government has to begin respecting the people," Residente told the crowd. "We can't stop protesting."
Protesters holding Puerto Rican flags, playing tambourines, and banging pots and pans were walking through the narrow streets of Old San Juan on their way to the governor's official residence, known locally as La Fortaleza.
"I'm here to fight for my rights and my daughter's rights," a protester, Andrea Batista, told CNN. "I'm tired of getting robbed."
Similar demonstrations were also planned in Miami and Orlando, Florida. "Hamilton" creator Lin-Manuel Miranda, former New York City Council speaker Melissa Mark-Viverito attended protests at New York's Union Square.
"I'm so numb from politics in America. But the people of Puerto Rico are numb and they are waking us all up. I'm going to have their backs," Miranda told CNN.
Earlier on Wednesday, Puerto Rico's Justice Department issued summonses for everyone involved in the private chat group with Rosselló.
The participants, which include 11 of the governor's top aides and Cabinet members, will be ordered to appear before department officials over three days and their cellphones will be inspected, department spokeswoman Mariana Cobian said.
Though Cobian said all participants of the private chat were being summoned, she declined to provide a list of names.
The FBI would neither confirm nor deny whether if it was separately investigating the chats, bureau spokesman Luis Rivera said.
Governor says he won't resign
Rosselló announced he would not step down Tuesday, hours after police fired tear gas into crowds of protesters calling for his ouster. He also defended the actions of police and accused protesters of unleashing tear gas and setting fires during demonstrations Monday night.
"I have not committed any illegal or corrupt acts," he said. "I committed inappropriate acts and have expressed regret for that."
The leaks came the same week that two former officials from Rosselló's administration were arrested by the FBI as part of a federal corruption investigation.
Rosselló has not responded to CNN's interview requests.
The governor promised to work to restore the public's confidence in him and noted that he has much work left to do.
"Despite the difficulties that we have internal and external, the work will continue and the agenda will be completed in all areas," he said. "You do not give up on work already started, and today, more than ever, a lot of people are counting on my commitment to do so."
If Rosselló were to resign, the law says the secretary of state, a post that is currently empty, is next in line to take the helm, followed by the island's treasurer.
San Juan Mayor urged residents to join protests
The messages, dubbed "RickyLeaks," contain profanity-laden, homophobic and misogynistic messages aimed at opposition politicians, journalists and celebrities.
Among the insults Rosselló hurls in the chats: He calls a Puerto Rican-born New York official a "whore" and says she should be beaten; says an oversight board managing the island's financial crisis can "go f*** yourself"; and tells one of this then-top officials that he'd be doing him a "grand favor" by shooting San Juan Mayor Carmen Yulín Cruz.
That official -- Christian Sobrino Vega, ex-chief fiscal officer and Rosselló's representative on the aforementioned oversight board, also was implicated in the withering chats, making a homophobic remark about singer Ricky Martin and mocking those killed in Hurricane Maria.
Yulín Cruz, a member of the opposition Popular Democratic Party who is running for governor, told CNN on Wednesday that the chats demonstrate that Rosselló and his supporters were hoping to silence their critics. She encouraged residents of her city, the territory's capital, to join in demonstrations demanding the governor's ouster.
"This is the people of Puerto Rico ... clamoring for whatever is left of our democracy to be saved so we can begin to move away from the darkness of Ricardo Rosselló," she said. "I am not advocating violence. I always advocate peaceful resistance, but just like (the Rev. Martin Luther King Jr.) said, I cannot condemn the indignation of people."
She has filed a report over what she called Rosselló's and Sobrino Vega's death threat against her, she said, and has called on the Legislature to begin impeachment proceedings immediately.
Ahead of Wednesday's protests in San Juan, Yulín Cruz said she won't allow police officers to block or injure demonstrators.
"I'm not going to cooperate with his (Roselló's) abuses. I won't be part of his efforts to criminalize the legitimate right of the people of Puerto Rico to ask for his resignation," she said.
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