08/27/2026
JURY CONVICTS PORTLAND MAN OF BURGLARY, THEFT OF PROPERTY | $10,000 - $60,000, AND FAILURE TO APPEAR
Today, following a three-day jury trial in Sumner County Criminal Court, Assistant District Attorneys Christopher V. Boiano and Eli M. Freeman secured convictions against Anthony Dale Gregory for Burglary, Theft of Property valued between $10,000 and $60,000, and Failure to Appear.
The charges arose from the November 2023 theft of approximately $18,000 in cash from the victim’s property in Portland, Tennessee. The proof at trial showed that Gregory had previously worked for the victim’s landscaping business, performing mowing and other work, and was familiar with the victim’s property. Gregory also knew about the existence of a safe on the property and the money kept inside it.
The victim had received approximately $18,000 from a personal injury settlement earlier that year. He last personally saw the safe and cash on November 16, 2023, when he retrieved some of the money before going out on a date with his wife. On November 23, 2023, the victim discovered that the safe and approximately $18,000 in cash were missing and immediately reported the theft to the Portland Police Department.
The investigation by Portland Police Department Detective Charles Hope uncovered significant circumstantial, financial, electronic, and cellphone-location evidence connecting Gregory to the burglary and theft. During an initial interview with Detective Hope on November 29, 2023, Gregory described himself as having very little money, at one point stating that he had only approximately $20 to his name.
As the investigation continued, Detective Hope discovered evidence of significant spending and attempted purchases surrounding the disappearance of the victim’s money. Investigators learned that Gregory purchased a four-wheeler for approximately $1,000 in cash on November 19, only days after the victim last saw the money. Facebook records obtained during the investigation also revealed communications concerning the attempted purchase of fi****ms, ATVs, dirt bikes, and vehicles.
Financial records provided additional evidence. Gregory had a bank account that had seen little or no activity for months. Beginning on November 30, 2023—one day after telling Detective Hope that he had approximately $20 to his name—Gregory began placing cash onto that account. Between November 30 and December 4, approximately $1,100 was loaded onto the account. Those deposits were followed by approximately 15 Amazon purchases.
Detective Hope also obtained cellphone-location information showing that Gregory’s phone was in the vicinity of the victim’s residence shortly after midnight on November 18, 2023. During the investigation, Gregory told Detective Hope that he did not go to the victim’s property at night.
The State also presented evidence of inconsistencies in Gregory’s explanations concerning his finances and purchases during November and December 2023. During multiple recorded interviews with Detective Hope, Gregory gave differing accounts concerning the source of money available to him and his involvement in certain transactions. At various points, Gregory claimed to have very little money while also explaining that he had saved cash from his mowing work during the summer.
Following the State’s proof, the jury found Gregory guilty of Burglary, Theft of Property, valued between $10,000 and $60,000, and Failure to Appear. Sumner County Circuit Court Judge Jennifer S. Nichols immediately revoked Gregory’s bond and ordered him held in the Sumner County Jail pending his October 20, 2026, sentencing hearing. Anthony Gregory faces a potential sentence of up to eight years in the Tennessee Department of Corrections, and then an additional mandatory consecutive sentence of eleven months and twenty-nine days, for his Failure to Appear conviction.
Gregory’s convictions would not have been possible without the outstanding investigative work of the Portland Police Department and lead investigator Detective Charles Hope. We are also grateful to Victim-Witness Coordinator Sally Ann Pirtle, who provided essential support to the victim, witnesses, and prosecutors throughout the case.
