Federal agents executed a dramatic raid on the luxurious North Naples residence of grocery titan Francis Alfred “Alfie” Oakes III, as well as his significant Immokalee produce packing facility, tirelessly transporting boxes throughout the day and into the night on November 7.
This extensive raid was conducted by multiple federal agencies, including the U.S. Secret Service, Defense Criminal Investigative Services, and the IRS. Notably, the operation unfolded just a week after Oakes’ wife, Deanne, received foreclosure papers for the second time regarding a substantial $4.1 million federal farm loan. According to a lawsuit filed on October 14, this legal action seeks to reclaim $2.78 million from both the couple and Oakes Farms OP, threatening the seizure of critical collateral, including essential farm equipment and crops, unless the overdue amount was settled by August 30.
While federal agencies remained tight-lipped regarding the connection between the raid, the looming foreclosure, and the staggering $18.1 million in contracts that Oakes has secured with the U.S. Department of Defense since 2008—primarily dealing with produce, dairy products, and eggs—official confirmations were notably absent.
Spokesperson Mollie Halpern of the DCIS confirmed the law enforcement activity at the location, stating, “I can confirm that DCIS, the law enforcement arm of the [Department of Defense] Office of Inspector General, conducted law enforcement activity yesterday at 925 New Harvest Road in Immokalee. We have nothing further to add at this time.” Meanwhile, the Secret Service offered an equally vague response, stating, “We are unable to provide comment as the U.S. Secret Service will not confirm the existence or the status of an investigation.”
Alfie Oakes did not respond to phone calls or texts seeking his comments on the raid but was seen leaving his South Florida Produce packing house behind the wheel of his royal blue Range Rover that afternoon. When approached by a WINK News reporter, he cheerfully declared, “Go Trump.” Upon being asked about the agents’ activities at his property, he assured her, “Everything is all good.” Later, upon returning home, he reiterated his support for Trump, shouting, “Go Trump, fight, fight, fight” to another WINK News reporter.
Speculation among local Republicans suggested that the raid on Oakes—an ardent supporter of former President Donald Trump and a former state GOP committeeman—might be politically motivated. Known for his significant political activities, Oakes financed two buses to transport Trump supporters to the U.S. Capitol for a protest concerning the 2020 election outcomes, one day prior to the infamous January 6, 2021, insurrection, where several attendees were later arrested.
Federal agents descended upon the Oakes’ residence on Santa Cruz Court in the upscale Villages of Monterey and his business, South Florida Produce, on a Thursday morning. Assisting with the operation, the Florida Highway Patrol secured the scene, allowing agents to methodically enter and exit while donning gloves and carrying important paperwork and boxes. Upon accessing his home, the agents departed with a collection of documents, boxes, and a computer after Deanne Oakes graciously let them in. They ultimately concluded their activities at his residence in the afternoon while continuing their investigation at the packing facility.
Local entrepreneur Danny Gonzalez, who is also the former president of the Immokalee Chamber of Commerce and an unofficial figure of authority in the area, reported that federal agents were still present at the packing plant when he returned home from work around 8:30 p.m.
Typical for the DCIS, their investigations focus on fraud, bribery, and corruption cases involving the Department of Defense, ensuring proper allocation of federal funds. They also tackle cybercrimes and hacking, terrorism prevention, and monitor the illegal transfer of sensitive defense technologies to potentially dangerous entities.
Federal records reveal that Oakes Farms Food & Distribution Services LLC has received an impressive $18.1 million in contracts from the Department of Defense since 2008, with a staggering total of 21,065 transactions primarily involving produce, eggs, and dairy products. The most considerable payments came in 2021, followed closely by 2022, with a gradual decline in payments observed into the following year. Various government entities, including the DOD, Department of Justice, Defense Logistics Agency, and Bureau of Prisons, were responsible for issuing these funds.
Moreover, Oakes Farms & Distribution Services LLC also acquired two minor DOD contracts. Cumulatively, these contracts amount to an astounding $36.3 million for essential fruits, vegetables, and perishable goods, with $3.3 million disbursed to Oakes, according to federal documentation.
In a notable achievement, Oakes Farms secured a generous five-year contract worth $238.5 million from the DOD in October 2022, charged with supplying fruits and vegetables to USDA-provided schools and various branches of the military, including the Army, Navy, Air Force, Marine Corps, and Coast Guard installations.
The foreclosure lawsuit, initiated by Farm Credit of Florida and filed in the Collier Circuit Court, details that Oakes Farms Inc. and the Oakeses secured a loan of $467,500 from the Florida Federal Land Bank Association on December 28, 2016. Over time, this loan underwent modifications in October and December 2018, eventually increasing the borrowing amount to $4.1 million through the inclusion of Oakes Farms OP LLC as a borrower.
As collateral for this significant loan, a total of six properties, which includes an array of crops and 114 pieces of vital equipment, machinery, and fixtures, were utilized; these properties were strategically located across various sites, including the primary address of 925 New Harvest Road, farms situated at 7455 and 7526 Sanctuary Road, crop land located at 1260 Deer Run Lane in Naples, and a packing facility at 837 E. Main St. in Immokalee. Furthermore, the collateral extended to encompass everything incorporated within all associated buildings, from doors and windows to cabinetry, carpeting, beds, and curtains.
Additionally, equipment and crops from Half Circle L Ranch, a property leased by Oakes straddling Collier and Hendry counties, were counted among the collateral, along with crops and a storage facility belonging to Gargiulo Produce, which the couple utilized. Furthermore, Synovus Bank was also listed as a defendant in the lawsuit due to another loan acquired by Oakes for a venture located on Davis Boulevard, a property that suffered significant flooding during Hurricane Ian on September 28, 2022.
With the farm loan maturing on January 1 and remaining unpaid, the couple subsequently presented a forbearance agreement to Farm Credit of Florida in May. This brief one-month agreement provided a respite from payments, enabling the couple to pursue refinancing options essential for settling the loan. The lawsuit, alongside summonses delivered to the couple in October, marked a crucial final step before potential seizure of their assets.
Despite his political involvement, Oakes faced challenges; he had previously served as the state Republican committeeman but was unable to run in the August primary due to misfiling the necessary forms with the Supervisor of Elections Office just before the noontime deadline on June 14. Renowned for his vigorous political campaign efforts, he has openly backed an extensive array of candidates.
During the COVID-19 pandemic, Oakes Farms Inc. benefited from $3.2 million in federal Payment Protection Loans through Synovus Bank intended to cover payroll obligations, as noted in records from the U.S. Small Business Administration. Organizations that accept PPP loans are eligible for forgiveness provided they meet specific criteria, such as maintaining employee positions throughout the loan duration. In this instance, the loans were deemed successful and subsequently forgiven, thus not requiring repayment.
Oakes received two substantial payments; the first aimed to retain 146 retail jobs through Oakes Farms Market LLC and the second to assist Oakes Farms Inc. in maintaining payroll for an impressive 355 farmworkers. His loans were amongst a considerable 8,845 PPP loans issued in Collier County, collectively preserving 7,216 jobs during the pandemic strain.
In 2020, he initiated a lawsuit against Collier County concerning the pandemic mask mandate, labeling it unconstitutional and invalid. He famously allowed patrons in his retail establishments to enter without masks. However, a federal judge dismissed the case in February 2023.
He also took action against the Lee County School Board, its superintendent, and other parties after the board terminated his food supply contract in June 2020. This contract termination coincided with Oakes’ controversial Facebook comments regarding the pandemic and the death of George Floyd, which led to claims his termination infringed on his free speech rights and Florida’s Sunshine Law. A federal judge dismissed this lawsuit in October 2023, reasoning that the Facebook comments addressed a “matter of public concern.”
Oakes remains entangled in two active lawsuits filed just last month. New York-based Seedway LLC, a seed provider with two warehouses in Florida, filed a suit concerning $384,333 in unpaid goods, alleging Alfie Oakes, Oakes Farms, and employee Steven Veneziano owe payments by the end of 2023. Furthermore, another lawsuit was raised against Oakes Farms Food & Distribution Services LLC by a former employee. This individual, whose wife experienced complications following childbirth in August, was terminated on September 14, before he could return to work after requesting additional time off due to family medical needs.
Notably, this is not the first occurrence of Oakes’ business properties being subjected to raids. In July 2014, state authorities raided Incredible Fruit Dynamics, located at 4206 Mercantile Ave., leading to the arrest of 105 workers for fraudulent documentation and related crimes. Oakes contended that he had no prior knowledge about their fraudulent activities, although several workers claimed he was aware of the situation.
**Interview with Political Analyst and Local Entrepreneur Danny Gonzalez Regarding the Alfie Oakes Raid**
**Interviewer:** Thank you for joining us, Danny. The recent federal raid on Alfie Oakes’ properties has captured significant attention. Can you tell us what your initial thoughts were when you heard about the raid?
**Danny Gonzalez:** Absolutely. My first reaction was surprise but not entirely shock. Alfie has been a prominent figure in both the business and political realms here in Southwest Florida. Considering his past political activities and involvement with the Trump campaign, it’s not entirely unexpected that he might find himself under scrutiny, especially given the recent foreclosure proceedings.
**Interviewer:** The raid involved multiple federal agencies, including the Secret Service and the IRS. What do you think prompted such a large-scale operation?
**Danny Gonzalez:** The involvement of several agencies hints at the complexity of the situation. Given that the IRS and the Department of Defense were present, it suggests they might be investigating potential financial improprieties linked to government contracts. Alfie’s company has secured substantial contracts with the DOD over the years, and with legal troubles on the horizon, federal agents may have deemed it necessary to step in and conduct a thorough investigation.
**Interviewer:** It appears that this raid occurred shortly after Oakes’ wife received foreclosure papers. Do you perceive a connection between the foreclosure and the investigation?
**Danny Gonzalez:** That’s a good question. On the surface, it certainly seems connected. Foreclosure proceedings can indicate financial instability, which might prompt a closer look from federal agencies, especially considering the significant sums involved in their loan agreements. The ripple effects of financial stress can often bring other underlying issues to light, including misconduct.
**Interviewer:** There’s been speculation that the raid may have political undercurrents, given Oakes’ strong support for Trump. Do you believe that politics could play a role in this investigation?
**Danny Gonzalez:** Speculation around political motivations is natural, especially when a high-profile supporter of Trump is involved. However, I would caution against jumping to conclusions. While politics can influence perspectives and narratives, the presence of federal agencies typically indicates that there are legal grounds for their actions. Their focus is usually on facts and evidence rather than political affiliations.
**Interviewer:** Oakes has a notable history of financing political activities, including transporting Trump supporters to Washington, D.C., prior to January 6. Do you think this could affect public perception of the situation?
**Danny Gonzalez:** Definitely. Alfie’s political involvement may color how different communities perceive this incident. Supporters might rally behind him as a victim of political targeting, while opponents might see this as a long-overdue consequence of his actions. Public perception will likely hinge on the outcome of the investigation and how Oakes chooses to respond.
**Interviewer:** What do you think this situation reveals about the intersection of business and politics in Southwest Florida?
**Danny Gonzalez:** It underscores how intertwined business and political networks can become, especially in a region like ours, where agriculture, local economy, and politics often overlap. Leaders in business can wield a lot of influence, but with that influence comes scrutiny, especially when public funds are involved. It’s essential for any community to stay aware of the dynamics at play.
**Interviewer:** Thank you, Danny, for sharing your insights on this unfolding story. It’s an engaging and complex situation that raises many important questions about both business practices and political connections in our community.
**Danny Gonzalez:** Thank you for having me. It will be interesting to see how this all develops in the coming weeks.