Tracking Trump's Deportation Flights: Ex-J.P. Morgan Exec Reveals All

The proposal by the Trump administration to revive the AlienEnemiesAct of 1798 had been under consideration well before March 15, although the exact timeline remained unclear. On that day, immigration lawyers headed to federal court aiming to prevent the government from invoking this exceptional wartime power, which permits deportations without proper legal procedures. At the time, there were minimal indications suggesting that the White House planned to utilize this act to transport groups of Venezuelans via airplane to be housed in a detention facility in El Salvador.

The initial individual to inform the public about these flight operations wasn’t someone from an official capacity, legal background, or press; rather, it was Tom Cartwright—a former J.P. Morgan executive residing in Ohio. He posted on social media, "TWO EXTREMELY UNUSUAL FLIGHTS WITH HEAVY ICING CONDITIONS heading from Harlingen to El Salvador." Noting this irregularity, he mentioned that U.S. Immigration and Customs Enforcement had used this particular path—departing from a town in South Texas—only one time over the last six weeks. His post concluded with speculation: “Could this be for deportations involving Venezuela?”

Immigration lawyers hurriedly returned to court. The subsequent few hours brought the nation nearer to a constitutional crisis than any previous confrontation between Donald Trump and the judiciary, as representatives from his administration disregarded D.C. District Court Judge James E. Boasberg’s directive to stop the deportations.

In this particular episode, Cartwright's involvement hasn't garnered much attention. However, during these last couple of months, as various organizations focused on immigrants' rights, legislative staff members, and journalists have found themselves grappling with monitoring the Trump administration's intensifying efforts to deport individuals, they've increasingly turned to Cartwright for assistance. At 71 years old, he is a dedicated advocate for immigration causes who, since retiring, has taken up the mantle of meticulously tracking U.S. deportation flights—a task not commonly highlighted by governmental sources.

Each day, he gathers information about ICE flights, utilizing expertise gained through overseeing financial institutions handling trillions of dollars. By leveraging openly accessible data from flight-tracking websites, he generates periodic reports—both weekly and monthly—that outline the destinations of ICE Air, which operates as the governmental body responsible for deportations via air travel.

[ Conor Friedersdorf: Trump is deporting 'them' in manners that pose a threat to us. ]

In recent weeks, Cartwright has emerged as the primary resource for individuals seeking information about the Trump administration’s deportations to Guantanamo Bay, their utilization of military aircraft, and the contentious trips to El Salvador. Both think tanks and legal groups reference his research. Over this past weekend, when The New York Times published a visual report The article explained that although President Trump made assurances about increasing deportations, the frequency of U.S. deportation flights hasn’t notably risen since he assumed office. This information was supported by "a New York Times analysis of an independent database," which happens to be Cartwright’s. His research served as the foundation for comparable findings. CNN story earlier this month.

During Trump’s initial term, Cartwright started monitoring ICE flights and kept providing monthly updates to reporters, nonprofits, and congressional personnel throughout the Biden presidency. However, with Trump vowing to remove " millions" during his next term and intensifying efforts by leveraging federal assets and aggressively employing executive powers, there has been an increased interest in Cartwright’s information lately.

He utilized readily accessible data that required significant effort to assemble and undertook a task that others weren't," said Adam Isacson, a border security analyst with the Washington Office on Latin America, a human rights group based in D.C. "I’m not sure whether he anticipated his secondary career would transform him into essentially the globe's sole reliable public resource for U.S. deportation flights precisely when these became a major component of one of America’s most prominent national headlines.

“He’s invaluable,” noted Robyn Barnard, a refugee advocate at Human Rights First, sharing her surprise upon initially discovering Cartwright’s experience in banking instead of advocacy work.

Mild-mannered and scholarly, sporting a gray beard and glasses along with an urbane demeanor, Cartwright adopts a more restrained perspective on his part in the country’s contentious immigration debate. "These individuals merit the respect of having their situation acknowledged," he stated when speaking about those being deported via ICE Air. "The entire procedure strips away their humanity."

ICE Air does not function as a typical commercial airline. Instead, it utilizes privately chartered planes with crews consisting of security personnel and ICE agents. These flights usually transport around 125 individuals who have been detained, all restrained with shackles and leg irons. According to ICE, such stringent safety protocols are essential for ensuring that the outnumbered staff members can keep control and stop detainees from trying to take over the cockpit or causing disturbances—incidents that have occurred before.

The American immigration enforcement system is famously unclear; unlike in the criminal justice system, Immigration and Customs Enforcement (ICE) usually refrains from releasing the identities of those they apprehend. Although ICE occasionally shares information about their operations through press statements, this disclosure tends to be selective and occurs according to their schedule. However, the private jets utilized by ICE carry registration identifiers that appear on various aviation monitoring platforms like FlightAware, Flightradar24, and ADS-B Exchange. These tools allow individuals like Cartwright to monitor these aircraft in real time as they fly overhead.

[ Quinta Jurecic: The definitive account of the Trump era ]

The task grew tougher after Trump administration officials began transferring immigrants via military transport planes, which do not show up on flight-tracking websites due to their lack of visible tail numbers and schedules. Cartwright tackled this challenge by utilizing these applications to monitor over a dozen airports from which U.S. military flights depart, searching specifically for aircraft without identifiable registration marks. He then corroborates this data with additional publicly available resources like local media accounts in areas where these planes were reportedly headed.

Cartwright mentioned that he dedicated approximately 20 hours per week to monitoring ICE flights prior to Trump taking office earlier this year. This has increased to between 30 to 40 hours currently. "It's become a daily task," he shared with me, sounding exhausted. "And there's nobody to take over."

Cartwright was raised in Springfield, Illinois, and eventually made his home in Columbus, Ohio, after advancing through the hierarchy at J.P. Morgan to assume the role of Chief Financial Officer overseeing one of the firm's biggest units, which encompassed 5,000 banking outlets. In his view, the advocacy efforts for immigrants that he took on post-retirement represent an extension of the principles he adhered to throughout his professional life. "In finance," he shared with me, "I genuinely believed we were assisting individuals." This statement might seem peculiar coming from a self-described progressive activist; however, Cartwright credits this belief as what initially drew him towards working in a local bank based in Springfield early in his career.

In 2015, during the height of the migrant crisis in Greece, Cartwright contributed his time as a volunteer. This was when lifeless bodies of immigrants who had perished in the water started appearing on the shores, most notably highlighted by an image of a young child that sparked international outcry and urged several European nations to take in additional asylum seekers. Later, under President Trump’s initial term, where he intensified actions against undocumented Central Americans—especially those traveling alone—he stepped up his involvement with refugee assistance. As someone deeply devoted to Catholicism, Cartwright commenced offering help at emergency accommodations managed by charitable organizations within southern regions of Texas. Additionally, he became part of the organization called 'Witness at the Border,' focusing on observing activities carried out by Immigration and Customs Enforcement (ICE) officials to document what they perceive as unjust treatment.

Cartwright shared with me that his inspiration came from another volunteer he encountered in Texas; this was an octogenarian woman observing deportees boarding an ICE flight. She counted each person aloud as they got on board. When Cartwright questioned whether she was attempting to calculate the number of individuals on the aircraft, "That’s not what I’m doing," she replied. According to Cartwright, "'I may not know their names,' she explained, 'but I am determined to ensure I witness every single one.'"

At the time, activist organizations were finding it difficult to determine where ICE was transporting individuals being deported. Although Cartwright had never utilized flight-tracking applications before, he possessed strong data management and analysis abilities that many of his fellow activists did not have. He explained to me that monitoring ICE flights helped alleviate the overwhelming sense of hopelessness associated with feeling as though nobody was paying attention or showing concern about what was happening.

Cartwright’s database indicates that ICE has conducted 267 deportation flights during the Trump administration, with the president utilizing military transport aircraft for these operations—these planes have operating expenses that are three to five times up to the altitude of typical passenger planes—at an extraordinarily rapid pace.

[ ICE isn't providing the extensive deportations President Trump desires. ]

Cartwright’s data indicates that the pattern and frequency of ICE operations have not substantially altered under Trump 2.0—a fact that could be unexpected considering the disputes and legal conflicts sparked by the administration's efforts to intensify immigration enforcement through increased arrests and deportations. Supported by various federal law-enforcement bodies activated by Trump, ICE agents conducted approximately triple the number of immigration arrests compared to the last few months of President Joe Biden’s tenure. However, due to a notable decline in unauthorized entries across the Mexican border, ICE now encounters fewer readily removable individuals. To achieve Trump’s objectives for deportation, ICE personnel are focusing their attention on identifying and apprehending more people who violate immigration laws within American urban areas and neighborhoods than was done throughout Biden’s presidency.

The Department of Homeland Security hasn’t instructed Cartwright to halt the publication of the information he gathers, he mentioned. Actually, he occasionally forwards his reports to ICE; however, he has yet to receive any feedback from them. When asked for comments regarding Cartwright’s data collection efforts, the agency failed to reply.

Cartwright emphasized the importance of precision in his reports when speaking with me. "Over 38 years in the finance sector, many of my documents ended up in SEC filings," he mentioned. "I never alter facts; it simply doesn’t align with who I am."

However, after completing approximately 35,000 Immigration and Customs Enforcement (ICE) flights, Cartwright confided in me that he feels exhausted. He looks forward to making his retirement truly permanent. Despite this, he still wishes for the efforts to carry on and has begun training several activists from Seattle who are eager to take over. He expressed willingness to impart all his techniques to others but also noted: "Some aspects can only be learned through experience; they cannot simply be taught."

He emphasized that what matters most to him is ensuring someone continues to watch over things.