THE MILLION-DOLLAR DRIVER: Getaway Wheelman Gets 3 Years in Federal Prison for Brazen Waterfront Jewelry Heist

By JOHN McCARTHY / V.I. Free Press News Reporter

CHARLOTTE AMALIE — A federal judge has sentenced the final members of an armed gang responsible for the terrifying, broad-daylight armed robbery of Gem and Gold Corner Jewelry Store, concluding a multi-year investigation into a heist that netted an estimated $1.1 million in stolen luxury goods.

While the masterminds received lengthy double-digit sentences, the getaway driver walked away with just 36 months behind bars—sparking intense community conversation regarding the legal math of federal plea agreements.

United States Chief District Judge Juan R. Robert sentenced Jamari Benjamin, 25, of St. Thomas, to three years in federal prison followed by three years of supervised release for his role as the operational wheelman during the September 19, 2020 assault. Benjamin was also ordered to pay part of a staggering $510,000 restitution bill to the store and its insurer, Dorchester Insurance (Topa Insurance Services).

Terror on the Waterfront

Court documents lay out a calculated, high-noon style ambush. At approximately 9:31 a.m., a white Suzuki Vitara pulled up to the Gem and Gold Corner storefront on the heavily trafficked Veteran’s Drive waterfront.

As Benjamin waited idling in the driver’s seat, the gang’s ringleader, Tashawn T.A. Warner, 25, and accomplice Shemar Webster, 23, stormed the facility. Both men were heavily masked and brandishing military-grade firepower, including an AK-47 assault rifle and a Glock 22 handgun.

Inside, the gunmen forced five employees—including two unarmed private security guards—to line up on the floor with their hands raised. During the chaotic takeover, Webster used his firearm to violently pistol-whip the store owner, causing severe lacerations to his head.

Warner and Webster shattered the glass display cases with the barrels of their weapons, sweeping gold and jewels worth $1.1 million into a large duffel bag. When the bag maxed out, they stuffed excess inventory into their pants pockets before sprinting back to Benjamin’s waiting getaway car.

The Disparity in Justice: 11 Years vs. 3 Years

The sentencing matrix handed down by Chief Judge Robert highlights the sharp contrast between the foot soldiers who brandished the weapons and the driver who facilitated their escape:

  • Tashawn T.A. Warner (Ringleader): Sentenced to 135 months (11.25 years) in federal prison.
  • Shemar Webster (Assailant): Sentenced to 125 months (10.4 years) in federal prison for his physical assault on the merchant.
  • Jamari Benjamin (Getaway Driver): Sentenced to 36 months (3 years) in federal prison.

Benjamin’s significantly lighter sentence reflects standard federal court protocols where non-violent cooperation, turning oneself in, and lack of direct violence inside the storefront heavily mitigate a defendant’s sentencing guidelines. While Benjamin drove the vehicle, he did not pull a trigger or wield a rifle, a distinction that saved him a decade behind bars.

Cracking the Case with Forensic Science

The initial escape sparked a high-speed pursuit through St. Thomas by Virgin Islands Police Department officers. The gang fled to Mafolie Hill, where Webster managed to switch to a second clean vehicle and escape to Atlanta, Georgia. Warner and Benjamin continued fleeing into the Bovoni Housing Community, eventually ditching the Suzuki Vitara and escaping on foot into the brush.

The critical breakthrough came down to old-fashioned detective work and modern forensic science. VIPD Forensic Officers thoroughly processed the abandoned Vitara, recovering discarded masks, gloves, and traces of the stolen jewelry. DNA profiles extracted from the masks and gloves directly tied Warner and Webster to the scene, dismantling their ability to deny involvement.

Facing airtight forensic evidence, Benjamin surrendered to law enforcement shortly thereafter. Webster was captured and extradited from Georgia in November 2020, and Warner was tracked down by federal agents a month later. A fourth individual, dynamic accomplice investigative target, was also sentenced to minor jail time after being caught attempting to hide the duffel bag containing the Glock 22 and cash in his trunk.

A Small Community Impacted

“The effects of gun violence are felt far and wide in our small community,” stated United States Attorney Delia L. Smith following the final sentencing hearings. She credited the collaborative, multi-agency investigation between the VIPD, the FBI, Customs and Border Protection, Homeland Security Investigations (HSI), and the DEA for delivering absolute resolution to the business community.

The case was aggressively prosecuted by Assistant U.S. Attorney Daniel H. Huston as part of the Organized Crime Drug Enforcement Task Forces (OCDETF) operations.

John F. McCarthy is a veteran journalist in the Caribbean.