Merritt Island Boat Captain Recruited for Perilous Smuggling Trips Involving Children and Pregnant Women
Michael Andrew Milano, a 44-year-old Merritt Island resident recruited as a boat captain in a clandestine human smuggling operation orchestrated by Brevard County roofing business owner Raymond Neil Smith, has been sentenced to just two years in federal prison for his role in trafficking migrants from Hati and the Bahamas to Florida. Milano, who pleaded guilty to bringing aliens into the United States, was caught red-handed on February 29, 2024, captaining Smith’s 42-foot Yellowfin vessel near the Brevard-Indian River county line. Florida Fish and Wildlife officers discovered 25 migrants crammed aboard – 21 Haitians and four Bahamians, including two pregnant women and four unaccompanied children. The vessel was equipped with firearms, night vision gear, and only a handful of life vests, highlighting the reckless endangerment inherent in the scheme. U.S. District Judge John Antoon imposed the 24-month sentence along with three years of supervised release and $5,100 in criminal assessments. Milano’s plea agreement also requires him to forfeit the seized guns and ammunition found on the boat.
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This sentencing follows closely on the heels of Smith’s own conviction, painting a fuller picture of a meticulously planned smuggling ring that ferried at least 90 illegal immigrants – many Haitian nationals and unaccompanied children – across the Florida Straits between July 2023 and February 2024. Smith, the 45-year-old owner of G&G Roofing in Rockledge, founded the multimillion-dollar company and cultivated a public image as a successful entrepreneur and family man. Behind this facade, however, he coordinated with facilitators in the Bahamas to recruit desperate migrants, charging hefty fees to transport them under cover of darkness. Smith exploited their vulnerability, instructing passengers to lie flat and remain silent to evade detection, all while profiting handsomely from their smuggling. Court documents reveal Smith was involved in six smuggling trips, recruiting Milano to captain the final three, which alone smuggled at least 90 individuals. In one intercepted voyage led by Milano at Smith’s direction, the migrants – including young unaccompanied children – were exposed on the deck without adequate safety measures, risking drowning in the treacherous waters.
Milano’s attorney, Kepler Funk of Melbourne, described the outcome as fortunate given the government’s push for a stiffer penalty. “It is very daunting for anyone going to court having the United States of America serve as the prosecution in a 25-count federal indictment,” Funk wrote in an email according to reporting from Florida Today. “In this case, the government sought a very stiff sentence for Mr. Milano, requesting numerous years in prison.” Funk added that the defense felt “very fortunate that 24 counts were dismissed and that the Court listened to our presentation of mitigation evidence for Mr. Milano and that our legal and factual argument resonated with the Court.”
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Ties to Wealthy Ringleader: Luxury Boats, Firearms, and Exploitation for Over $284,000 in Illicit Gains
The operation leveraged Smith’s affluent lifestyle and resources. He deployed two luxury offshore fishing vessels – the 42-foot Yellowfin and a 2020 42-foot Freeman, together estimated at $2 million – to transport the migrants, evading Coast Guard and Border Patrol under the cloak of night. Federal investigators traced $284,000 in cash proceeds from the smuggling directly to Smith, which he attempted to launder through third parties. These profits stemmed from exploiting migrants as commodities, with some even shuttled as undocumented labor for Smith’s properties, including a private island in the Bahamas, bypassing official immigration checkpoints. A Homeland Security informant confirmed captaining trips for Smith to move his own roofing workers without visas.
Smith’s $1.8 million waterfront home in Rockledge, featuring a pool overlooking the Indian River, served as a launch point for these illicit voyages. On April 19, 2024, agents observed individuals loading duffel bags onto Smith’s Freeman vessel at his residence. The boat was stopped offshore, revealing four Honduran nationals and two U.S. citizens aboard; Smith claimed they were en route to work on his Bahamian property. This incident, combined with Milano’s earlier arrest, unraveled the conspiracy. Smith pleaded guilty to conspiracy to smuggle aliens and unlawfully transporting aliens, receiving a 30-month sentence in May from U.S. District Judge Gregory Presnell. He was ordered to forfeit the two boats, the $284,000 in proceeds, and pay $40,200 in criminal penalties.
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Reached days after his sentencing, Smith declined to comment in detail, expressing to Florida Today that he didn’t think it was newsworthy, that “nobody was hurt,” and described the situation as “unfortunate.”
The contrast between the smugglers’ opulence and the migrants’ desperation is profound. Smith and Milano treated human beings – including children separated from families and pregnant women – as cargo for profit, while living in luxury. Yet both men will likely spend less time in prison than many of the trafficked migrants endure in U.S. immigration detention centers like Alligator Alcatraz, where undocumented individuals can languish for months or years awaiting processing, often in overcrowded facilities. This disparity is evidence of a troubling reality: the perpetrators of human smuggling face relatively brief consequences, while their victims bear prolonged hardship.
Lenient Sentences Amid Community Support Letters for Ringleader Smith
Both sentences reflect stunning leniency given the crimes’ severity. Milano’s 24 months and Smith’s 30 months fall far below federal guidelines, which could have warranted up to 10 years per count. For Smith, guidelines initially recommended 8 to 10 years, yet he received a significant downward departure. Milano similarly avoided the maximum 10-year term and $250,000 fine for his charge.
A pivotal element in Smith’s light punishment was an avalanche of 42 character reference letters submitted to the court, pleading for mercy. These came from family, friends, employees, and local civic leaders, portraying Smith as a generous community pillar. These letters from community leaders noted Smith’s financial contributions to their organizations, funds which very well could have came directly from Smith’s human smuggling profits. Notably, endorsements included representatives from respected non-profits like Junior Achievement and Habitat for Humanity – organizations dedicated to uplifting children and families – despite his trafficking of minors. Smith’s substantial donations, exceeding $100,000, and volunteer efforts, such as providing free roofing and plywood before hurricanes or aiding businesses during COVID-19, seemingly secured this support. Letter writers highlighted his acts of kindness, framing his crimes as an aberration. This network of influence, built through philanthropy and business ties, helped recast Smith as deserving of compassion, influencing the judge to impose a mere 2.5 years. Like Smith, some authors of the letters which were submitted in their official capacities like Anne Conroy-Baiter who wrote a letter on behalf of Junior Achievement of the Space Coast, tried to down-play the charges as a “misunderstanding” or simply an “E-Verify mixup,” once we published the letters. It’s highly likely that many who chose to write a letter of support for Smith were unaware that they would be a matter of public record. (All of the letters will be posted at the end of this article, below are some referenced above.)
While no such letters are noted for Milano, his association with Smith’s operation ties him to the same web of privilege that enabled the ring. The defense’s receptivity to mitigation for these men – despite endangering lives for greed – prompts questions about equal justice.
Light Punishments Undermine Deterrence in Ongoing Immigration Debates
Amid national emphasis on border security, where smuggling is decried as fueling crises and endangering migrants, these sentences stand out for their mildness. Smith and Milano’s scheme involved nearly 100 vulnerable individuals, profiting from desperation while risking tragedy – yet they face minimal time behind bars. Immigration advocates note that detained migrants often endure longer separations and hardships than these smugglers will serve. Smith’s dismissive attitude – claiming no harm and questioning newsworthiness – exemplifies a detachment from the human cost. As Brevard County grapples with this case, it exemplifies how connections and wealth can soften justice’s blow, even in egregious human trafficking cases, leaving observers to ponder if true accountability exists when privilege intervenes.
