Oak Bluffs Police investigation leads to multiple larceny arrests

Jason Reagan, right, and Jason Willoughby. – Courtesy Greg Arpin

After a week-long investigation, full of unusual twists, Oak Bluffs police placed Jason Reagan, 36, of Oak Bluffs, under arrest on Feb. 1 for a charge of breaking and entering in the daytime with the intent to commit a felony, larceny over $250, and larceny from building.  The investigation led police to three more people connected to the crime and eventually, to some of the stolen goods at the bottom of the Lagoon.

The investigation began on Jan. 25 after an East Chop resident reported that a large amount of cash, a laptop computer, cell phones and other property was missing from his home.

Oak Bluffs police Lt. Tim Williamson told The Times that the theft appeared targeted for a specific area of the house. Reagan became a person of interest after the homeowner said he had done work there six months prior to the break-in. The homeowner was apparently aware of Reagan’s criminal record.

That night, Oak Bluffs police put Reagan under surveillance at his home on Worcester Avenue, where his lives with his girlfriend Hillary Seaton, 41. They noted a car registered to Tyrone Barlosky, 36, of Tisbury, in the driveway.

The night after the break-in, Jan. 26, an officer saw Reagan walk to the Lagoon and return a few minutes later. At the time, no incriminating evidence was found on the path to the Lagoon or on the shore, which was largely submerged by high tide.

Police caught a break when an informant told them that they had heard Barlosky bragging about a heist of a large amount of cash.

Then on Feb 1, police got a call about a domestic disturbance at the Reagan/Seaton household, for a dispute over money.

“When we got to the house, Reagan said ‘she stole $50,000 from me,’” Lt. Williamson said. “At the time we thought it was $20,000 that had been stolen but we later confirmed with the victim that it was a minimum of $50,000. Jason went on to make a lot of incriminating statements.”

Seaton turned $7,700 over to police Reagan had given her to buy a new car.

Police determined that Reagan had paid $2,000 for Seaton’s legal fees in her appeal of the Oak Bluffs selectmen’s unanimous decision to euthanize her pit bull.

A search of the house didn’t turn up any more cash.

Reagan told police that he had found the $50,000, but he didn’t recall the location. He told police he had burned the backpack that contained the money at the end of the path to the Lagoon.

Lt. Williamson said another search of the path and the beach at the Lagoon showed no sign of any burned material. But owing to an astronomically low tide, a white object was visible on the bottom of the Lagoon.

“The night they checked the beach it was high tide and there was only a few feet of beach. We were there in daylight and there was 30 feet of beach,” Lt. Williamson said.

The white object turned out to be a laptop computer and there were two cell phones beside it.

“Sure enough, the serial numbers matched the items stolen in the robbery,” Lt. Williamson said.

Regan and Barlosky told police they had given $2,000 to Jason R. Willoughby, 32, of Tisbury, $800 for the purchase of drugs and $1,200 for a loan. While the arrest warrant was being written up for Willoughby, Oak Bluffs police were informed by Tisbury police that they had arrested him on drugs charges.

Tisbury Police Lt. Eerik Meisner told The Times that Willoughby was arrested on a charge of possession with intent to distribute Fentanyl on Tuesday. He was arrested at a residence at 190 Bernard Circle, based on a search warrant and arrest warrant.  

In addition to the drug charges, Barlosky was summonsed under the joint venture theory and charged with receiving stolen property over $250.

Reagan is currently being held at the Dukes County jail on a probation violation.
Willoughby has an extensive criminal record and is currently being held at the Dukes County jail.

Seaton will be charged with receiving stolen property over $250.

The investigation remains open. Anyone with information is asked to contact Oak Bluffs Police Department detectives at 508-693-0750.



  1. are these guys Brazilians ? ok, sorry, but I can’t help but troll the racist here– No comments about this speaks volumes about the racist.. If these guys were from anywhere but here, the racist trump supporters would be calling for them to be thrown in jail forever or deported.. Sorry guys, trump is a racist, and if you support him, you are also..

      • There are certain leftists here who use every posting opportunity to call the President a racist – even if he has no connection whatsoever to the matter at hand. Pathetic

        • hanley– let’s remember that the next time someone with a foreign name gets busted for something.. I have enough brain cells to remember that every time an immigrant got busted , the “righties” blamed Obama.. Perhaps you forgot that already.
          And I still think we should build a wall around Oak Bluffs..
          I might also note you are not criticizing Capawok for bringing up Omarosa , but you don’t like her, so I guess that’s ok ?

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