A Sumner County jury has convicted a former landscaping employee of burglary and theft after prosecutors say he used inside knowledge of his old boss's safe to steal roughly $18,000 in cash from a Portland, Tennessee property. Anthony Dale Gregory, 40, was found guilty following a three-day trial in Sumner County Criminal Court on charges tied to a November 2023 break-in, along with a separate failure to appear conviction. He was booked into the Sumner County Jail on Thursday with no bond after a judge revoked his release.
According to the Portland Police Department, Gregory previously worked for the victim's landscaping business and knew about both a safe kept on the property and the cash stored inside it. The victim had received approximately $18,000 from a personal injury settlement, the department says, and had last personally seen the safe and cash on November 16, 2023. By November 23, the victim discovered the safe and money missing and reported the theft to Portland police the same day.
Detective Charles Hope, the department's lead investigator on the case, built a circumstantial case using financial records, digital communications and cellphone location data rather than eyewitness testimony, per the department's account. Investigators say Gregory's phone was in the vicinity of the victim's residence shortly after midnight on November 18, 2023, two days after the victim last saw the cash and safe intact.
A Bank Account That Suddenly Filled Up
When Detective Hope interviewed Gregory on November 29, 2023, Gregory said he had only approximately $20 to his name and claimed he had saved cash from mowing and other work he performed over the summer of 2023, the police department states. He also told Hope he had not gone to the victim's property at night. But bank records told a different story, according to police: Gregory's account had shown little or no activity for months, then began receiving cash deposits starting November 30, 2023, totaling roughly $1,100 loaded on by December 4.
Those deposits were followed by approximately 15 Amazon purchases, and Facebook records reportedly revealed communications about attempted buys of dirt bikes, ATVs, firearms and vehicles. Investigators say Gregory also purchased a four-wheeler for about $1,000 in cash on November 19, 2023, just one day after his phone's location placed him near the victim's home. Police say Gregory gave differing accounts about where his money came from and his involvement in the various transactions.
Consecutive Sentences Loom in October
Assistant District Attorneys Christopher V. Boiano and Eli M. Freeman secured the convictions on theft, burglary and failure to appear. Under Tennessee Code Annotated § 39-14-105, theft of property valued between $10,000 and $60,000 is a Class C felony carrying three to 15 years in prison, according to Justia Law. Burglary of a non-residential building is a Class D felony under Tennessee Code Annotated § 39-14-402, punishable by two to 12 years, per the same statutory framework.
Gregory faces a potential sentence of up to eight years in the Tennessee Department of Corrections on the primary charges. Because he was also convicted of failure to appear, state law requires that sentence be served consecutively rather than concurrently — an additional 11 months and 29 days tacked onto whatever term he ultimately receives, as FindLaw explains of the statute governing missed court dates.
Sumner County Circuit Court Judge Jennifer S. Nichols revoked Gregory's bond following the verdict and ordered him held in the Sumner County Jail pending his sentencing hearing, scheduled for October 20, 2026. Nichols was appointed to the 18th Judicial District circuit court bench in July 2024 after previously serving as an Assistant District Attorney in Sumner County, Hoodline has previously reported. She and Boiano worked together as recently as March, when they secured a 15-year prison sentence for a serial fraudster in a separate Sumner County case, according to the Sumner County Source.
New DA's Office Pursues High-Dollar Cases
The prosecution comes under newly appointed District Attorney General Thomas B. Dean, who took over the 18th Judicial District in September 2025 after Ray Whitley retired following 45 years as Tennessee's longest-serving district attorney, Main Street Media of Tennessee has reported. Detective Hope, who joined the Portland Police Department in September 2015 and moved into the Criminal Investigations Division in 2022 after serving as a patrol sergeant and field training officer, was credited by the department with assembling the digital and financial evidence that anchored the case.
Sally Ann Pirtle served as victim-witness coordinator, providing support to the victim, witnesses and prosecutors throughout the case, the police department noted. FBI crime data shows burglary and property crime rates in Sumner County generally remain below national averages, Hoodline has reported, though cases like Gregory's show property theft investigations remain a steady focus for local detectives. The victim, according to police, had retrieved some of the settlement money before going on a date with his wife shortly before the theft was discovered.
Gregory's final sentence remains undetermined until Judge Nichols rules at the October hearing, when the consecutive terms for theft, burglary and failure to appear will be calculated together.
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