ABC 7 Chicago spoke to the mayor of San Juan in Chicago Thursday and she sent a strong message to the president.
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"The President of the United states, every time he speaks ill of Puerto Rico, he manifests his incompetence, his ignorance, and his inability to be Commander in Chief," said San Juan Mayor Carmen Yulin Cruz.
Cruz was in Chicago meeting with the Reverend Jesse Jackson. She thanked him for organizing a supply trip to bring food, water, and other goods right after Hurricane Maria hit.
"As the mayor of San Juan, I will forever be grateful to you," she said.
But with Cruz's trip came a sobering reminder of the destruction that still has thousands of island families living in deplorable conditions.
"There's still about 45,000 families that have rooftops that are blue roofs or tarps," Cruz said. "So in the next (weakest) of hurricanes they will have to be evacuated."
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Those facts run counter to President Trump's opinion.
"I think that Puerto Rico was an incredible unsung success," Trump said earlier this year.
According to advocacy group the Puerto Rican Agenda, more than 2,000 evacuees have been helped here in the Chicago area. The official city welcome center closed in May.
"We have begun to rebuild houses in Puerto Rico, we have retrofitted community centers, we have helped to create new infrastructures in some of the areas," said Puerto Rican Agenda Senior Adviser and Puerto Rican Cultural Center Executive Director Jose Lopez.
But there is only so much community organizations can do without additional federal help.
"He needs to, for the sake of the world, in the next two years, start to understand what his role is, start to understand what leadership is all about," Cruz said about President Trump.