A 55-year-old UPS driver, Dennis Michael Millwood, has been apprehended and charged with second-degree grand theft following a law enforcement sting operation in Florida. Millwood’s arrest, which took place on June 25, stems from allegations that he pilfered a Rolex watch valued at approximately £55,000 while on duty.
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The investigation, conducted by both UPS investigators and the Miami-Dade Sheriff’s Office’s Organised Retail Crime (ORC) Squad, was initiated after a series of reported thefts involving packages that went missing in transit from the Hialeah distribution centre.

According to documents obtained from the arrest affidavit, surveillance footage played a pivotal role in the case against Millwood. Investigators purportedly captured him on camera removing packages from an area not designated for his delivery assignments and subsequently loading them into his UPS vehicle.
On June 9, an investigator observed Millwood loading a sizeable package into his truck—a package that was not part of his allocated route. When confronted, Millwood claimed it was a mix-up, insisting that the package had been incorrectly loaded and that it was meant for another driver responsible for rerouting misdirected packages. Upon its delivery, the recipient discovered that the expensive Rolex watch was missing from the package.
The investigation revealed that Millwood had been found with other packages not assigned to him. On one occasion, authorities alleged that four additional packages were discovered in his vehicle, one of which had been opened and then resealed, raising further suspicions regarding his conduct.
In a bid to catch Millwood in the act, officers from UPS and the Miami-Dade Sheriff’s retail crime unit orchestrated a carefully planned sting operation on June 25. They utilised two sealed packages containing Samsung mobile phones and a GPS tracking device, which were rigged with a special security dye. This dye is engineered to release a noticeable red stain if the package is tampered with without permission.
As the operation unfolded, investigators observed Millwood taking the two monitored packages and placing them into his truck. Authorities later followed Millwood for part of his delivery route. At a location in Miami, he reportedly opened one of the packages, leading to the activation of the security dye that marked his hands in red. Witnesses noted that Millwood appeared frantic as he attempted to remove the dye using towels and paper before he continued with his deliveries.
Later that day, investigators detained him while searching his truck, where they discovered the resealed package that he had attempted to conceal. During subsequent questioning by law enforcement, Millwood acknowledged recognising the Rolex box but denied any involvement in the theft of the luxurious item.
He divulged to investigators that he had given the stolen watch to a friend named Chris, after having kept it for a week, but was reluctant to provide further details about this individual. As part of his response, Millwood suggested he would be willing to retrieve the watch and return it if he were released.
In an intriguing turn of events, Millwood allegedly confessed to routinely taking packages outside his designated deliveries, which indicates a pattern of behaviour that may have gone unnoticed prior to the sting operation.
The case has highlighted significant issues around package security during transit, particularly for high-value items. As investigation efforts continue, both the authority and UPS are likely looking to reinforce their protocols to prevent future incidents of theft, ensuring that package deliveries uphold the trust of their customers. Millwood’s trial will now determine the legal ramifications of his actions amidst rising concerns over package theft in the delivery industry.
