Derrick Shaw
•7/20/2026
Senior U.S. District Judge John E. Steele, who spent more than two decades on the federal bench in Fort Myers and presided over some of Southwest Florida's most significant criminal and constitutional cases, has died at the age of 77.
Steele was appointed to the federal bench in 2000, giving the Fort Myers Division a permanent U.S. district judge. Before his appointment, the division relied heavily on visiting district judges from elsewhere in the Middle District of Florida.
He became one of the most recognizable figures in Southwest Florida's federal court system, overseeing thousands of civil and criminal cases.
His death came just days after a nationally watched immigration ruling involving Maikel Guerra Morales, a Cuban national convicted of hijacking an aircraft in 2003. On July 8, Steele ordered Guerra Morales released from U.S. Immigration and Customs Enforcement custody while deportation efforts continued.
In his ruling, Steele found that under U.S. Supreme Court precedent, the federal government could not continue to detain Guerra Morales indefinitely because there was no significant likelihood he could be removed in the reasonably foreseeable future.
The decision quickly drew national attention.
Florida Rep. Greg Steube later introduced articles of impeachment against Steele, arguing the judge had exceeded his judicial authority in ordering the release. The Department of Homeland Security also released a statement on the Guerra Morales ruling.
Throughout his career, Steele presided over several cases that became defining moments for Southwest Florida and, in some instances, attracted national attention.
In 2009, Steele sentenced Fort Myers real estate broker Samir Cabrera to 10 years in federal prison after Cabrera was convicted of defrauding investors of nearly $2.8 million during the collapse of the region's housing market.
In 2022, Steele presided over the federal trial of Fort Myers businessman Casey Crowther, who was convicted of fraudulently obtaining more than $2 million in Paycheck Protection Program funds and using some of the money to purchase a luxury catamaran. Steele sentenced Crowther to more than three years in federal prison. The case was widely viewed as one of the nation's first major prosecutions involving fraud tied to federal COVID-19 relief funds.
Steele again found himself in the national spotlight in 2025 when he ruled that restrictions imposed by the City of Naples on an outdoor Naples Pridefest drag performance likely violated the First Amendment. His preliminary injunction temporarily allowed the event to proceed in Cambier Park while the legal challenge continued, placing the case at the center of a national debate over free speech, LGBTQ rights and government regulation of public events.
To acknowledge public speculation, as of Monday, there has been no indication from court officials or other authorities that Steele's death was related in any way to his recent immigration ruling or the impeachment effort.
No additional information about funeral arrangements or memorial services has been publicaly released.
