After borrowing $10,000 from his elderly employers last August, home-care assistant Cory Kisakye never worked again for the couple or returned to their Jamaica Plain townhouse — until he allegedly broke in and stole a 17-carat diamond ring three months later.
According to police reports and court records, Kisakye, 27, of Randolph, used his insider knowledge of the couple’s home to break in, unlock their safe, then make off with large diamonds, gold, watches, and pearls.
Kisakye was arrested after police said he fled to Florida — and briefly Uganda — following the alleged crime. He was arraigned on charges of larceny from a building, unarmed burglary, and breaking into a depository. He will be back in West Roxbury District Court for a dangerousness hearing Thursday.
His lawyer, Andrew Stockwell-Alpert, told the Herald that he was communicating with the Suffolk County District Attorney’s Office about the hearing, and what other issues might be discussed in court.
In addition to the 17-carat rock, estimated to be worth $850,000 alone, the safe also contained a 4.9- and 11-carat diamond rings, two Piaget watches (valued at $20,000), De Grisogono block earrings (valued at $18,000), and two of the couple’s wedding bands, the documents noted.
When the couple, who are in their late 80s, spoke with police, they said that Kisakye had once helped change the battery to the safe and had access to the code. They also told police about the unpaid loan.
After the defendant cashed the $10,000 check, which was supposed to help him pay for a new car, according to the report, the couple said he “refuses to answer their phone calls and has never attempted to repay them.”
Two months after he abruptly stopped working for the victims and a month before the crime, GPS data from a rental car showed Kisakye returned to the area with the intent, the report said, “to conduct a dry-run and/or reconnaissance mission for the November burglary and jewelry heist.”
GPS data from his cellphone as well as a fingerprint found on a Bloomingdale’s bag left in the safe after the burglary placed him at the scene of the crime, according to court records, although investigators noted that they believed he had at least one accomplice on the night of Nov. 18.
Surveillance footage shared by the victims showed two hooded individuals leaving the townhouse just before midnight. Only Kisakye has been charged in connection to the break-in.
There were 46 items in the safe, some of which Kisakye allegedly pawned and sold to feed a substantial gambling habit. According to the police reports, he “spent a significant amount of time at Encore,” in Everett.
He made 55 trips between October 2024 and December 2025, the report said, with a total cash in of more than $142,000.
A few weeks after the burglary, Kisakye sold an $11,000 18kt gold Italian bracelet to a shop in Miami, Florida, using his Massachusetts driver’s license as an ID during the transaction, the reports said. When police showed a photo of the piece to one of the victims, she immediately recognized the bracelet as hers.
Kisakye allegedly made several queries using ChatGPT after the burglary, the reports said, including:
- “Can you estimate carats of diamond in picture… how much is 3 ct like that worth”
- “What kind of tiffany bracelet is this”
- “How much is this diamond worth worst case scenario if its natural”
In addition to the allegation surrounding the November heist, the documents noted that according to Randolph Police reports, Kisakye was also involved in two prior incidents involving a stolen Xbox and a stolen 1.8-carat ring.
Between Dec. 2024 and Aug. 2025, prior to the alleged crime, the report said Kisakye had made 14 pawn shop transactions, including selling jewelry, silverware, Cartier sunglasses, and a PS5, in which he made $9,670.
Kisakye was between Massachusetts and Florida following the break-in, until purchasing a one-way ticket to Uganda on Dec. 9. The report said police believe Kisakye might have been tipped off to the investigation by someone he sold gold to.
It isn’t clear when or why Kisakye returned to the U.S., but Boston Police said he was taken into custody on May 26 in Miami.
