Gregory Bovino Roasts Trump’s DHS From the Sidelines After Retirement

Gregory Bovino, who led aggressive immigration raids in Chicago and other cities under the Trump administration, has found a new battleground since retiring last month: publicly trolling his former DHS colleagues on social media.

Bovino, once a staunch enforcer of Trump’s immigration crackdown, now uses his X (formerly Twitter) account to slam the federal government for what he sees as a softening stance on immigration enforcement. In one pointed response to a DHS claim that illegal immigrants cost taxpayers nearly $8,776 annually, Bovino fired back, “Then restart mass deportations and quit messing around with it.”

This is no casual grudge match. Bovino’s posts reveal deep fractures within the Trump administration’s immigration policy. While officials like border czar Tom Homan initially pushed for targeting the “worst of the worst,” the administration soon shifted toward sweeping raids aimed at hitting high arrest numbers, often at the expense of civil rights and community trust.

Former Customs and Border Protection Commissioner Gil Kerlikowske described the internal struggle as a “food fight,” noting that the shift from targeted enforcement to mass raids led to disastrous results in cities like Los Angeles, Chicago, and Minneapolis. In Chicago, for example, the Operation Midway Blitz sparked widespread racial profiling and the teargassing of peaceful protesters.

Bovino’s own exit from Minneapolis was mired in controversy after the fatal shootings of Renée Good and Alex Pretti by federal agents. His leadership was questioned, and after conflicting narratives with then-Homeland Security Secretary Kristi Noem unraveled, Bovino retired.

Since then, Bovino has not held back, making outlandish claims such as 100 million unauthorized immigrants living in the U.S.—a figure that would represent roughly a third of the population. He advocates for policies so harsh that undocumented immigrants would be forced to “self-deport.”

The Department of Homeland Security declined to directly address Bovino’s comments but insisted that “ICE is NOT slowing down” and that DHS law enforcement remains committed to President Trump’s promise to keep America safe.

Bovino’s social media tirades lay bare the ongoing tensions and contradictions within Trump’s immigration enforcement approach: a tug-of-war between ruthless mass deportations and a more “targeted” strategy that still results in widespread abuses and community harm.

For those tracking the Trump administration’s immigration policies, Bovino’s new role as a retired critic offers a rare insider’s glimpse into the chaos and cruelty behind the headlines. And his relentless trolling shows that even after leaving office, the fight over America’s immigration future is far from over.