'Operation Cupid's Nest'; Court Documents Shed Light on Immigration Enforcement at Puerto Rico Airport

G.L.P. was attempting to pass through an airport checkpoint at Luis Muñoz Marín International Airport when he was stopped by two Customs and Border Patrol (CBP) officers who asked him "where he was going and what his nationality was." The interaction led to him being detained by immigration authorities after he admitted he was a Dominican citizen without a United States visa or resident card.

He was a target of "Operation Cupid's Nest," which "involves asking all travelers in the TSA checkpoint line their flight destination and their country of citizenship,” reads an affidavit supporting G.L.P.'s arrest warrant signed by a Federal Bureau of Investigation (FBI) agent reviewed by Heavy Weather.

The document does not contain any more information about the mandate and scope of Operation Cupid’s Nest.

When questioned about Operation Cupid’s Nest, a CBP spokesperson said the agency “does not make public comments regarding matters before U.S. courts.” Meanwhile, a Transportation Security Administration spokesperson claimed it "does not have any TSA equity."

G.L.P. pleaded guilty to improper entry and resisting a federal officer, and was released from Federal Bureau of Prison custody in early March. However, it is unclear if he remains in the U.S. or if he has been deported. He does not show up in the Immigration and Customs Enforcement (ICE) detainee locator tool. His full name and court records are being withheld to protect his identity.

G.L.P. is one of at least five Dominican citizens without a regularized migration status in the U.S. who have been detained at Luis Muñoz Marín International Airport between February and March, according to court documents reviewed by Heavy Weather. The five migrants have all been charged with either improper entry into the U.S. or re-entry after being removed, according to court records.

Two are currently being held at MDC Guaynabo, a federal detention center in Puerto Rico.[[1]] Although one of them was about to get out on bail, a family member contacted the probation office and said "their only desire [was] to return to the Dominican Republic as soon as possible," according to court records. A migrant who was released from MDC Guaynabo after spending 18 days there was transferred to the Broward Transitional Center in Florida after pleading guilty, according to court records and the ICE detainee locator tool.

Because Puerto Rico's only migrant detention center was closed in 2011, undocumented migrants detained by immigration authorities in the archipelago are only held for a short time in the archipelago before being shipped to Florida or another state with available bedspace.

"These people are arrested and taken to the United States. Then, they lose contact with their community," said Mari Mari Narváez, executive director of Kilómetro 0, a non-profit that tracks police abuse. Once they are outside of Puerto Rico it becomes much harder for migrants to find legal representation because they have no connections in the area where they are being held, she explained. Kilómetro 0 is part of a group of pro-immigrant civil society and activist organizations called the "Broad Front Against Trump's Immigration Policies."

A USA TODAY investigation found that five women in “ongoing legal immigration process[es]” who felt comfortable travelling on domestic flights were detained in mid-February at airport checkpoints in Puerto Rico and the U.S. Virgin Islands. One of the women was detained at the Luis Muños Marín International Airport while returning from her honeymoon.

“No foreigner who has problems with their immigration status should be approaching any airport or any port of entry,” warned Julie Cruz Santana, an immigration lawyer. She was not surprised to hear that CBP is undertaking a named immigration enforcement operation at the Luis Muñoz Marín International Airport because one of her clients was detained there in February.

She explained that, in some cases, migrants married to U.S. citizens who are applying for permanent resident status are being detained by immigration authorities because they end up overstaying their visas while waiting for their application to be processed.[[2]] Putting extra strain on immigration courts by arresting migrants already in process of gaining their permanent resident status will only make the delay in processing applications worse, she warned.

“These are visceral policies against immigration. They are visceral policies against the family unit, which at the end of the day, are the ones who are most affected,” Cruz Santana said. 

However, immigration checks are not only affecting undocumented migrants or those currently in the process of applying for permanent resident status and citizenship. The continued drive to target migrants has led to immigration authorities targeting American citizens who seem like they could be undocumented migrants. 

The same day G.L.P. was detained, Iliana Pacheco was stopped by an Immigration and Customs (ICE) agent while passing through the TSA checkpoint. He asked Pacheco — an American nurse of Mexican descent who had come to Puerto Rico as part of a Valentine’s Day getaway — what her migration status was and to see her passport. She was confused because the TSA had just checked her license before she stepped into the baggage search area.

“Give me your passport now,” Pacheco recalled the ICE agent spitting out while she tried to explain she was an American citizen. Her partner stepped in to say that he did not have his passport because American citizens only need a valid license to travel on domestic flights. However, it was not until she showed the ICE agent her passport that she was allowed to continue through the checkpoint. Pacheco asked him why she had been stopped and he simply said she “fit the description.”

Shaken, she went up to another ICE agent to ask what description they were talking about. The agent told her that anybody fitting the description of an undocumented migrant would be stopped and questioned. The agent's statement caused her heart break into a million pieces, she recalled.

“Is this really what people feel like every day? Is this what my parents go through?, Is this what every single first generation son, daughter of immigrants — is this really what they go through,” she remembered asking herself at the time.

It is unclear if all these people – outside of G.L.P. – were targets of Operation Cupid's Nest or just detained as part of regular immigration enforcement at airports in Puerto Rico and the U.S. Virgin Islands.

TSA checkpoints can quickly lead to immigration officials detaining several people without a regularized migration status. Approximately 15.4 million travelers were screened by a TSA checkpoint during the week of Valentine’s Day in 2025, according to TSA data. The mixture of surveillance and databases that immigration officials have access to at airport checkpoints has led to multiple people being arrested, deported, and in one case, allegedly tortured, according to The Verge.

Nearly 280 migrants have been detained by immigration authorities in Puerto Rico since President Donald Trump came into office, according to a recent television interview with Rebecca González Ramos, who leads Homeland Security Investigations (HSI). The agency has been at the forefront of media coverage of immigration enforcement since Trump signed his first immigration-focused executive orders.

An HSI spokesperson claimed the agency did not participate in Operation Cupid’s Nest.

Operation Cupid's Nest is likely one of many operations that have been undertaken by federal immigration authorities across the U.S. as part of the Trump administration’s “immigration enforcement blitz,” which has led to 33,242 arrests according to the Department of Homeland Security (DHS).

Recently, the Trump administration invoked the Alien Enemies Act – the same 18th century law that put people of Japanese descent in concentration camps during World War II – to rendition 238 Venezuelans to El Salvador's Terrorism Confinement Center (CECOT, in Spanish) under the excuse of them being members of MS-13 or Tren de Aragua, which were recently designated a foreign terrorist organization.

The families of some of the people renditioned to CECOT have already come out to say they were not gang members. One of the migrants, who does not have any criminal record, was granted refugee status and flew to the U.S. in January, which is where he was detained, according to the Miami Herald. Another man, with no criminal record in Venezuela, was purportedly sent to CECOT because of his Real Madrid football tattoo, according to El País English. The Trump administration is seemingly using tattoos as a guarantee that Venezuelan migrants are gang members even when there is no other proof. 

The FBI [[3]] and DHS did not respond to requests for comment. Heavy Weather submitted Freedom of Information (FOIA) Act requests to CBP, ICE, and the FBI concerning records about “Operation Cupid’s Nest.” The FBI and CBP denied the records requests. However, Heavy Weather appealed the denials and is currently awaiting the agencies’ determination. 

[[1]]: Correction: A previous version of this article misidentified MDC Guaynabo as the only federal prison in Puerto Rico. However, it is an administrative detention center.

[[2]]: Correction: A previous version of this article oversimplified the migration process and substituted "citizenship" for "permanent resident status."

Correction: A previous version of this article misidentified MDC Guaynabo as the only federal prison in Puerto Rico. However, it is an administrative detention center.

Correction: A previous version of this article oversimplified the migration process and substituted "citizenship" for "permanent resident status."

[[3]]: A week after this article was published, the FBI responded to Heavy Weather's request for comment to say they "cannot confirm or deny the existence of an investigation."