A Madison man who was sentenced to nine months in jail in a plea agreement with prosecutors in December 2017 might be heading back to jail after his arrest this week.

Jonathan Tyler Cayford, 26, was arrested Wednesday on a probation violation for allegedly harassing another person in Madison. He also was issued a summons on a charge of harassment, said James Ross, chief deputy with the Somerset County Sheriff’s Office.

Cayford, originally charged with manslaughter in connection with a fatal 2015 crash in Starks, pleaded guilty to a charge of driving to endanger in exchange for dismissal of the manslaughter charge.

Cayford was charged for his role as the driver of a car in which Clint J. Briggs, also of Madison, was killed and two others were injured on Nov. 13, 2015, in a crash on Anson Road in Starks.

Briggs, 21, was found dead at the scene, the Somerset County Sheriff’s Office said at the time.

Ross said this week that Deputy Chelsea Merry responded Wednesday to a complaint of harassment in Madison, with Cayford being named as the person doing the harassing. He said Cayford had been warned earlier in the day about harassment involving the same person.


While Merry was at the house of the person who reported being the victim, viewing text messages and calls, the deputy saw a vehicle turning around in front of the house. The resident identified the vehicle and Cayford.

Jonathan Tyler Cayford

Merry stopped the vehicle and arrested Cayford on a probation hold at the request of Cayford’s probation officer. Merry also summonsed Cayford on a harassment charge, Ross said.

Asked about the case, District Attorney Maeghan Maloney no comment on the substance of it.

“We have not received the (probation violation) motion yet. We expect to receive it next week,” she said.

Cayford was sentenced to five years in prison with all but the nine months suspended. If he violates his probation with any new criminal activity, he could serve some or all of the suspended portion of the sentence. His probation is for two years and remained in effect this week.

He also was ordered to surrender his driver’s license for two years.


In the fatal crash in 2015, police said Cayford, driving west, was passing a line of other westbound vehicles at a high speed when he went off the road.

Deputies at the scene estimated Cayford’s speed at 80 mph. Police said that as the vehicles he was passing approached a corner in the road near the intersection of Olde Ferry Road, Cayford lost control of the 1998 Nissan Maxima, striking several trees.

Cayford was taken to Redington-Fairview General Hospital in Skowhegan after the crash. A 17-year-old female passenger in the front seat was taken by LifeFlight of Maine helicopter to Eastern Maine Medical Center in Bangor. Her name was not released. She survived the crash.

Cayford admitted to the civil violation of “causing death,” for which he was ordered to pay a $1,000 fine, which was suspended to community service work, and another four years of license suspension, for a total of six years of license revocation.

Cayford also was sentenced to 10 days in jail to run at the same time for violating a protection from abuse order.

His lawyer at the time, Brad Grant, of Waterville, said his motion in court to dismiss the initial charge, citing violations of discovery rules involving police notes as evidence from the crash, was denied by a judge in Skowhegan court.

“From our perspective, the manslaughter charge, they were claiming that his conduct caused the death, and I think the experts showed that his conduct may have caused the accident,” Grant said in December 2017. “But there were other issues that caused the death, for instance the integrity of the car. So he pled guilty to driving to endanger and not manslaughter.”

Grant could not be reached for comment Friday on the new charges.

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