Ryan Kentrell Montgomery, 37, has been handed a two-year federal prison sentence for his role in the St. Patrick’s Day 2023 smash-and-grab at Heller Jewelers in San Ramon, a takeover-style robbery that netted about $1.1 million in Rolex watches and other high-end pieces. Court filings and local coverage say the sentence caps a multi-year federal investigation that leaned heavily on digital breadcrumbs and physical evidence to tie suspects to the daylight heist.
How investigators tracked the crew
According to investigators, a stolen Rolex outfitted with a hidden GPS chip quietly did much of the early heavy lifting. The tracker allegedly let law enforcement follow suspects’ movements and connect a specific vehicle to the Heller Jewelers robbery. Phone and iCloud records then helped map out what prosecutors describe as coordinated movements on and around March 17, 2023. Those details surfaced in coverage from National Jeweler and earlier reporting in Rolex GPS chip cracks $1.1M heist.
Arrests, pleas and earlier sentences
Four of the five defendants eventually pleaded guilty and were sentenced in 2024 to prison terms that ran from roughly three to three and a half years, even as investigators kept pulling on threads to understand the broader network behind the daytime takeover. Local reporting notes that the group was rounded up after an August 2023 series of arrests and a related Oakland raid that turned up weapons and other evidence tying the crew to the crime. As reported by Danville San Ramon.
Montgomery’s sentence and prosecutors’ view
Federal prosecutors told the court that Montgomery’s own phone records put him at or near Heller Jewelers during the robbery and that additional digital evidence linked him to other members of the crew. A federal judge in Oakland imposed a two-year term today, following arguments that laid out how the data trails allegedly connected Montgomery to the $1.1 million hit. The Mercury News detailed the hearing, prosecutors’ position and the judge’s decision. As reported by The Mercury News.
A wider Bay Area trend
The Heller case is part of a broader wave of coordinated smash-and-grab attacks that has hammered jewelers across the Bay Area in recent years. Heller Jewelers was hit again in September 2025, and a separate June 18, 2025 smash-and-grab at Kumar Jewelers in Fremont left that store with an estimated $1.7 million loss, underlining how organized crews have zeroed in on high-end display cases across multiple cities. See reporting in the Los Angeles Times and NBC Bay Area for the 2025 incidents.
Restitution and next steps
Court records show that the earlier defendants were ordered to pay restitution to Heller Jewelers and will remain under supervised release once they finish their prison terms. Prosecutors have said the investigation required coordination among federal and local agencies and could still lead to additional charges as remaining leads are worked. Those requirements and potential next steps are outlined in court filings and sentencing notices reviewed by local outlets. As reported by Danville San Ramon.
Content of article sourced from Hoodline- San Francisco.