The hurricane wiped out the island's power grid, and fewer than half of residents have running water.
Some Democrats roasted the Trump presentation, noting that much of the island still lacks food, potable water, and electrical power.
President Donald Trump had claimed in a tweet that Cruz was being told by Democrats to be nasty to him, after she begged for help for the residents of the us territory in the aftermath of Hurricane Maria.
Cruz donned the shirt during an interview with Jorge Ramos on Univision's "Al Punto" and said it was in response to remark's made by the president, who described her as "nasty" after she criticized him for failing to provide adequate relief following Hurricane Maria.
Ms Cruz wore the shirt during an interview in which she attacked the President for his visit to Puerto Rico after the USA territory was devastated by a hurricane. Images on Twitter and other social media platforms showing previous US Presidents embracing, hugging victims of tragedies in the past were ample evidence to suggest that what the 45th US President lacks.
"Texas & Florida are doing great but Puerto Rico, which was already suffering from broken infrastructure & massive debt, is in deep trouble", the president tweeted last Monday.
In the interview Wednesday, Cruz said that she intentionally wore the shirt to hit back at Trump. "They owe a lot of money to your friends on Wall Street, and we're going to have to wipe that out", Trump said.
She went on to say that she gets along with P.R. governor Ricardo Rosselló, who is a "tireless collaborator", even though the two share different visions about life. Trump, by contrast, has a habit of attacking anyone who criticizes his policies or disagrees with what he says.
On a more positive note, Cruz said: "I saw a real connection between the reality and the White House staff".
Mr Trump, who has grappled with hurricanes Harvey, Irma and Maria in the past six weeks, praised the federal assistance so far in the United States territory but not without a remark about its financial cost. "I don't know if it's Goldman Sachs, but whoever it is, you can wave goodbye to that".
Hours after President Donald Trump arrived in Puerto Rico Tuesday to survey the damage wrought by Hurricane Maria and toss paper towels into a crowd, dozens of protesters, including City Council Speaker Melissa Mark-Viverito, gathered one block from Trump Tower in Manhattan, demanding that his administration do more.
Trump and other administration officials have worked in recent days to reassure Americans that recovery efforts are going well and combat a perception that the president failed to fully grasp the magnitude of the storm's destruction in its immediate aftermath. "Stop blaming Puerto Rico for the storm that devastated their shores, and roll up your sleeves and get the recovery on track".
At press time, President Trump was scheduled to visit Puerto Rico on Tuesday.
The Federal Emergency Management Agency said more than 12,000 federal officials are now on the ground on the island, and 45 percent of customers now have access to drinking water. The island's previous governor had declared that debt unpayable.
The board sent a letter to Congressional leaders Tuesday pleading for "the maximum federal assistance to Puerto Rico", including grants and low-interest loans, saying the island will "face severe cash shortfalls from lower revenues, higher costs, and delayed or reduced cost-saving measures".