A UPS package reached its intended recipient in Miami-Dade County, but investigators say the $55,000 Rolex watch that was supposed to be inside was missing when the box was opened.
Local 10 reported that Dennis Michael Millwood, 55, of Miramar, Florida, was arrested Thursday after a weeks-long investigation by UPS investigators and the Miami-Dade Sheriff’s Office Organized Retail Crime Squad.
According to an arrest report cited by the station, investigators were looking into packages whose contents disappeared while moving through UPS’s Hialeah distribution center.
Millwood has been accused of taking packages that were not assigned to his delivery route and loading them into his UPS truck. The allegations have not been proven in court.
WSVN published courtroom video from Millwood’s first appearance.
The Box Arrived, But The Watch Was Missing
A UPS driver was arrested Thursday after Miami-Dade Sheriff’s Office detectives said he stole packages while on his delivery route, including one containing a Rolex watch valued at about $55,000.
— WSVN 7 News (@wsvn) June 26, 2026
The investigation focused partly on a package containing a Rolex watch valued at approximately $55,000. Local 10 reported that surveillance video from June 9 showed Millwood loading the package into his truck, and tracking data later confirmed the package remained inside his vehicle.
Investigators said Millwood later told UPS the package had been mistakenly loaded onto his truck and transferred to another driver responsible for rerouting misdirected deliveries.
The package ultimately reached the intended recipient, but investigators said the Rolex was missing when the box was opened. UPS investigators said RFID data confirmed the package had been inside Millwood’s truck before it was delivered.
Investigators Say He Took Packages From The Wrong Area
According to Local 10, investigators reviewed surveillance video and alleged that Millwood routinely arrived before his scheduled shift and removed packages from the “Lakes Box Bottom Slide,” an area containing packages that were not assigned to his route.
Those packages were then loaded into his assigned UPS truck, investigators said. Packages assigned to Millwood’s route were normally loaded from a different conveyor system, according to authorities.
Investigators also alleged that on Wednesday, Millwood selected four additional packages that were not assigned to his route. One of those packages was later found opened and resealed.
A Sting Package Released Red Dye, Deputies Say
WSVN reported that detectives and UPS investigators used two controlled packages during a Thursday operation. The packages contained Samsung cellphones, GPS tracking devices, and a security dye pack.
Authorities said Millwood loaded the controlled packages into his truck even though they were not assigned to his route. While stopped in a Miami neighborhood, investigators said he opened one package, causing the dye pack to activate and stain his hands red.
Detectives said they saw Millwood trying to wash the dye from his hands before continuing deliveries. He was later taken into custody during a delivery stop in the North Miami area.
WSVN reported that Millwood faces one count of second-degree grand theft and was scheduled to appear in court Friday. Local 10 reported that he was facing multiple felony charges.
High-Value Packages Need More Than A Tracking Number
The case is a warning for anyone buying, selling, or shipping expensive items. A tracking number can show that a box moved through the system or reached a destination, but it does not always prove that the item inside arrived safely.
For watches, jewelry, electronics, collectibles, and other high-value items, buyers and sellers should keep receipts, serial numbers, order confirmations, photos, tracking records, and messages with the seller or carrier. If the item is shipped, use declared value or insurance where available and require a signature for delivery.
When a package arrives, inspect it quickly. Look for torn tape, resealed seams, missing weight, damaged packaging, or anything that suggests the box was opened before delivery. Photograph the package before throwing anything away, especially if the contents are missing or different from what was ordered.
UPS says claims for lost or damaged packages should be started within 60 days of the scheduled delivery date. The company also says claims require supporting documentation, such as an invoice showing the value of the missing merchandise, and that damage claims may require photos or inspection.
If an expensive online order never arrives, or arrives without the item that was purchased, the Federal Trade Commission advises consumers to contact the seller first. If the seller does not fix the problem and the charge appears on a credit-card statement, the FTC says the consumer can dispute the charge as a billing error.