Kisakye was arraigned Wednesday in West Roxbury District Court, and was ordered held without bail. He pleaded not guilty, and a hearing is slated for Thursday to determine if he is a danger and flight risk who should remain jailed pending trial.
Kisakye started working for the homeowners as a home-care assistant in December 2023, according to a police report. He helped change the batteries to the basement safe last summer, the report says.
And he had intimate knowledge of the property, including the safe’s combination, police said.
On Nov. 19, the homeowners called 911 because their dog started barking nonstop and they were worried someone was lurking around the property, located inside a gated community on Allandale Road, according to police. Officers responded to the address and searched outside the home, finding nothing amiss. But later that morning, they discovered the back door was unlocked and the safe had been emptied.
The police report contains a long list of stolen items, including a 17-carat diamond ring worth an estimated $850,000.
On Dec. 9, Kisakye bought a one-way ticket to Uganda and departed the same day, declaring $54,000 in cash, according to the report.
Detectives later obtained surveillance footage showing two hooded figures leaving the Jamaica Plane property around midnight Nov. 19, according to the report.
Police said the suspects gained access to a locked safe room and emptied its contents, including diamond rings, luxury watches, gold bracelets, and designer pieces from brands such as Tiffany and Co., Piaget, and Chopard — worth several million in total.
They ultimately zeroed in on Kisakye, noting his long history of “thefts, check fraud and pawning jewelry.” Police reports in Randolph had already linked him to a stolen diamond ring and a residential burglary where an Xbox gaming system was stolen. He had also made 14 pawn transactions between December 2024 and August 2025, according to the Boston police report.
A fingerprint at the crime scene was identified as belonging to Kisakye, police said, and GPS data placed him in the area of the home around the time of the burglary and on a suspected scouting visit about a month prior.
Boston police allege that after breaking into the Jamaica Plain home, Kisakye tried to sell the stolen jewels in various states, including Massachusetts, New Hampshire and Florida, before fleeing to Uganda “upon learning that investigators were inquiring about him.”
He started communicating with and visiting a local jeweler less than 48 hours after the break-in, police say. Within days, he traveled to Miami, where he allegedly sold a stolen gold bracelet for $11,000, according to police.
Detectives found suspicious activity in his financial transactions dating back years, including evidence he had opened accounts “in the name of a deceased individual for whom he had previously served as a caretaker,” according to the report. His criminal record includes fraud charges in Florida and Michigan, according to the report.
Police also noted his extensive gambling activity, including at the Encore in Everett.
It’s not clear when Kisakye returned to the United States from Africa or how police finally tracked him down in Miami. On Tuesday, Boston police brought him back to Suffolk County.
He faces felony charges of unarmed burglary, breaking into a depository, and larceny from a building, court records show.
An attorney representing Kisakye declined to comment Thursday.
Shannon Larson can be reached at shannon.larson@globe.com. Follow her @shannonlarson98. Lea Skene can be reached at lea.skene@globe.com. Follow her on X @lea_skene.
