LITTLETON – On Monday, Aug. 31, 2026, at approximately 8:27 a.m., a 64-year-old Littleton resident contacted the Littleton Police Department to report that his vehicle had been broken into the previous evening.
(The account and quotations in this article were sourced from the printed Statement of Facts of Sergeant Pablo Fernandez and do not reflect any political perspective or personal opinion of News Link Live, which is strictly a business entity.)
According to Littleton Police Sergeant Pablo Fernandez, Officer James Morine was assigned to call the reporting party back at the number he provided.
“Upon call back, [the reporting party] stated to Officer Morine that the night prior, he had mistakenly left his vehicle unlocked and the keys in his truck, which he said was a Chevy 1500 pickup,” Sergeant Fernandez said. “When [the reporting party] went to leave for work around 7:00 a.m., on Aug. 31, 2026, he noticed his backpack was missing along with his wallet containing $100 in cash, three bank cards, and a credit card along with his ID.”
The reporting party told Officer Morine that he had shut the lights off and went to bed at around 11:00 p.m. the previous evening.
“[The reporting party] stated to Officer Morine that he was currently at work and had his vehicle with him,” Sergeant Fernandez said. “He told Officer Morine that he did not have security cameras on his property. Moments after disconnecting the call, [the reporting party] called back and stated his son’s car was also broken into.”
The reporting party said his son’s car was also parked in his driveway on Buttonwood Way.
Sergeant Fernandez said that after the second call with the reporting party ended, the reporting party’s son called and spoke with Officer Morine.
“[The reporting party’s son] told Officer Morine that he noticed his backpack containing his gym clothes and shoes were missing, along with his AirPod earbuds,” Officer Fernandez said. “[The reporting party’s son] stated the AirPods had a location ping feature and that they were pinging at 168 Tahattawan Road all morning.”
The reporting party’s son said the AirPods pinging feature also indicated that they had been moving on I-495 North in Chelmsford and then stopped in Lawrence.
Officer Morine asked the reporting party’s son to call if the location changed again or if they returned to Littleton.
“Later that day, [the reporting party’s son] called back and stated that the AirPods were pinging at 373 King Street in Littleton,” Sergeant Fernandez said. He added that the reporting party’s son later provided Officer Morine with screenshots from his phone of the AirPods pinging at 168 Tahattawan Road and 373 King Street.
Sergeant Fernandez said that 168 Tahattawan Road, which is less than a mile away from the residence on Buttonwood Way where the car thefts allegedly took place, is a single-family ranch style residence that he and other members of the Littleton Police Department are familiar with because it is the residence of 34-year-old Kyle Smith.
“Mr. Smith is well known to members of the Littleton Police Department and has accumulated more than 80 adult criminal arraignments,” Sergeant Fernandez said. Adding, “Many of these matters are theft-related and include charges for breaking and entering, including nighttime breaking and entering into both residences and motor vehicles. Mr. Smith also has an extensive history of drug-related offenses.”
Sergeant Fernandez added that Smith has multiple convictions for theft and breaking and entering.
“In 2022, Mr. Smith served a sentence at the Billerica House of Corrections after being convicted of breaking into motor vehicles in Littleton, Massachusetts, during the overnight hours,” Sergeant Fernandez said. “In 2023, Littleton police arrested Mr. Smith on two separate occasions for offenses related to domestic violence. Mr. Smith was subsequently sentenced to and served approximately nine months at the Billerica House of Corrections for those offenses.”
Sergeant Fernandez added that another individual who lives on Nashoba Road also reported to the Littleton Police Department that on the morning of Monday, Aug. 31, 2026, his vehicle had been broken into the evening prior.
Officer Stephen McAvey was assigned to call the second reporting party back.
“Upon call back, [the second reporting party] stated to Officer McAvey that their vehicle, a 2017 gray Toyota Camry was left at home all day,” Sergeant Fernandez said. “[The second reporting party] told Officer McAvey that they were certain that their car was left unlocked.”
The second reporting party said that his mother was home all day on Aug. 30, 2026, and that he arrived back home at around 10:00 p.m.
“[He] said they went to be shortly after,” Sergeant Fernandez said.
The second reporting party said that at approximately 7:00 a.m., when he was getting into his car to leave for work, he noticed that most of the contents from the center console of his vehicle had been removed and thrown onto the floor in front of the passenger seat.
“[The second reporting party] noticed that the only items missing were two $50.00 Amazon gift cards,” Sergeant Fernandez said.
The second reporting party asked his mother if she went into his car overnight and she said she did not.
Officer McAvey asked if there were security cameras at the residence, and the reporting party stated there were not.
On Thursday, Sept. 3, 2026, at approximately 10:19 a.m., Sergeant Fernandez said that he and Lieutenant Patrick O’Donoghue called the initial reporting party’s son and asked if his AirPods were still actively pinging and showing location of the AirPods.
“[The initial reporting party’s son] told us that the AirPods were still actively pinging and, ‘As of an hour ago they were at 168 Tahattawan Road,” Sergeant Fernandez said. Sergeant Fernandez said the initial reporting party’s son sent him a screenshot of the ping showing the AirPods at 168 Tahattawan Road.
Later that day, Sergeant Fernandez said Lieutenant O’Donohue met with the initial reporting party’s son to obtain a written statement from him.
“[The initial reporting party] was also present,” Sergeant Fernandez said. “During that occasion, [the initial reporting party’s son] and [the initial reporting party] provided Lieutenant O’Donohue with a handwritten list of other items and property both victims realized were missing.”
Sergeant Fernandez said the items stolen from the first reporting party’s vehicle had an estimated total value of approximately $1,400, while the items stolen from his son’s vehicle were valued at approximately $625.
On Friday, Sept. 4, 2026, at approximately 1:20 p.m., Sergeant Fernandez called the initial reporting party’s son and spoke with him over the phone.
“[He] confirmed that the AirPods were continuously pinging at 168 Tahattawan Road,” Sergeant Fernandez said. “[The initial reporting party’s son] told me they have been pinging at 168 Tahattawan Road continuously throughout the week.”
On Sunday, Sept. 6, 2026, at approximately 11:16 a.m., Sergeant Fernandez contacted the initial reporting party’s son via text message.
“[He] stated in the text message, ‘Just so you know, the AirPods have pinged at this address all weekend,’” Sergeant Fernandez said. “[The initial reporting party’s son] sent a screenshot of the ping showing the AirPods at 168 Tahattawan Road.”
On Tuesday, Sept. 8, 2026, Sergeant Fernandez said he traveled to Ayer District Court and submitted a search warrant application and accompanying affidavit to the assistant clerk magistrate, which was subsequently granted.
On Wednesday, Sept. 9, 2026, at approximately 6:00 a.m., investigators from the Maynard, Pepperell, and Littleton police departments met to debrief on the execution of the search warrant at Smith’s residence at 168 Tahattawan Road.
“Upon arriving at the residence, I along with other officers present, observed an adult male exit 168 Tahattawan Road and begin to light a cigarette,” Sergeant Fernandez said. “I quickly knew this male to be Mr. Smith. By that point, investigators were walking up the driveway and Officer James Morine, in full uniform, identified himself and placed Mr. Smith into handcuffs. Officer Morine and I advised Mr. Smith that we were there at his home with a valid search warrant. Mr. Smith was searched by Officer Morine while I was present and the remaining investigators knocked, announced themselves, and then entered into the residence of 168 Tahattawan Road for the purpose of securing it.”
Sergeant Fernandez said that while investigators were clearing and securing the residence, he asked Smith if his mother was home and Smith said she was.
“That information was relayed to the investigators,” Sergeant Fernandez said. “I learned later on that Mr. Smith’s mother…was found in the residence getting ready for work.”
At around this time, Sergeant Fernandez said he told Smith that police were there with a search warrant for the home and that the search warrant was for stolen property.
Sergeant Fernandez then read Smith his Miranda rights from a card he carries in the pocket of his police vest.
“After reading the Miranda rights to Mr. Smith, I asked if he understood those rights, to which he said he did,” Sergeant Fernandez said. “I asked Mr. Smith a series of questions regarding my investigation to which he responded to indicating that investigators would find stolen property in his bedroom. Having knowledge that Mr. Smith has a history of drug use, I asked him if investigators would find narcotics present in the home or more specifically in his room, to which he answered no.”
While executing the search warrant at Smith’s residence at 168 Tahattawan Road, investigators located the following items:
- Debit cards and bank cards belonging to other individuals (found in or on a bureau in Smith’s room)
- Several pink, round prescription pills (found in or on a bureau in Smith’s room)
- Two sets of AirPods (found in a backpack in Smith’s room)
- Three black cases containing prescription glasses and sunglasses (found in a backpack in a closet in Smith’s room)
- A Braven Bluetooth speaker (found in a backpack in a closet in Smith’s room)
- A brown wallet containing the initial reporting party’s identification and cards was found inside a backpack in a closet in Smith’s room.
- Three cases of off-brand AirPods were located in a backpack in a closet in Smith’s room
- Bank cards belonging to a separate male individual were found in pant pockets in Smith’s room
- A pair of Saucony running sneakers were found in a backpack in a closet in Smith’s room
Following the execution of the search warrant, Kyle R. Smith, 34, of Littleton, was arrested and charged with the following:
- Receiving Stolen Property +$1200
- Receiving Stolen Property -$1200
- Possession of Class E Drug
Smith was arraigned in Ayer District Court on Sept. 9, 2026. Following his arraignment, he was released on personal recognizance under the condition that he have no contact with the victims and stay away from their residences in Littleton.
Smith’s next court date is a pretrial hearing scheduled for Oct. 16, 2026.
Disclaimer: If you are wondering why the incident in this story took place in August, that’s because I had to file FOIA request(s) to obtain the court documents. FOIAs are time-consuming.
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