A convicted sex offender wanted by local, state, and federal authorities was arrested on a Plymouth bike path last week after a vigilant police officer came across warrants for his arrest and went looking for him.

Christopher Chassey, 57, was ordered held without bail by a Plymouth District Court judge on April 28, facing multiple charges of failing to register as a sex offender.

He will be jailed until a May 15 hearing, according to court records.  

Chassey, who had lived in Plymouth and Middleborough, was stopped by Plymouth patrol officer Andrew Whelan, who began his shift on April 25 by scrolling through a state computer system that tracks warrants.

He saw that Chassey was wanted by Middleborough and Plymouth police, as well as the US Marshals Service, for alleged probation violations.

Whelan visited a few places in Plymouth where Chassey had stayed, but did not find him.

Suspecting he was still in the area, Whelan expanded his search, making his way by motorcycle to the North Plymouth Rail Trail, a popular route which links the waterfront to Cordage Park.

He spotted Chassey, who allegedly tried to hide his face.

“Christopher?” Whelan asked. “Yes,” he answered.

He was arrested on the spot.

Middleborough police and the US Marshals helped Plymouth police in their investigation, according to Plymouth Police Chief Dana Flynn.

Chassey was placed on the state’s Sex Offender Registry in 2017 after pleading guilty to federal charges of enticing a person to engage in sex.  

He was sentenced to time served — one day in federal custody — and 20 years’ supervised release, the federal equivalent of probation, records show. The case was brought by the US Attorney in Rhode Island, but his probation was transferred to Massachusetts.

For the first year, he was confined to his Plymouth home with electronic monitoring. He was also required to participate in a sex offender treatment program, submit to polygraph tests, and unannounced searches of his electronic devices. He was also ordered to stay away from children, court records show.   

The charges stemmed from a series of exchanges between Chassey and someone he met on Craigslist through an ad he placed seeking a “young” sexual partner, according to court documents.  

He and a teenage boy, who claimed to be 14, traded emails for several months. Chassey sent him money, court documents say.

Finally, the teen — who was an undercover agent — pressed for a meeting. Chassey sent him a train ticket so they could meet in Plymouth.

When Chassey showed up at the train station for the rendezvous, he was arrested.

He was ordered to register with the Massachusetts Sex Offender Registry as a Level 2 offender — the second most serious category — and comply with a long list of probation terms.

According to court documents, he complied with the requirements for a few years.

But starting in 2020, he allegedly violated several rules: He failed to register as a sex offender, failed to notify the probation department or Plymouth or Middleborough police when he changed addresses, and he continued to look for partners on Craigslist, court records say.

In 2021, his federal probation officer filed court papers referring to Chassey’s “blatant disregard” for the terms of his probation.

Before Chassey was sentenced in the federal case, his lawyer implored the judge not to send him to prison.

The lawyer, Olin Thompson, who was federal defender, described Chassey as a “kindhearted…autistic, homosexual man who has …lived with his parents for his entire life. He is loved and respected in his community. He has no criminal record whatsoever.”  

“He was extremely cooperative with law enforcement and explained honestly that he did sometimes engage in Internet chats or personal meetups with men younger than himself” but never with anyone under the age of 19, which he knew was wrong,” Thompson wrote.

The original charge was enticing a minor for sex, but ultimately, he pleaded guilty to enticing a person for sex.

“While the advisory guideline sentencing range appropriately calls for some time of imprisonment in this type of case, Mr. Chassey’s unique personal situation clearly calls for a non-incarcerative alternative,” Thompson wrote.  

“Mr. Chassey feels appropriately remorseful and does not require prison to show him his mistake. There is no actual victim requiring retribution.”

“Properly supervised, he is at minimal risk to reoffend,” he wrote.

Richard McLeod, a lawyer who was appointed to represent Chassey on the Plymouth probation violation charges, could not be reached for comment.

Andrea Estes can be reached at andrea@plymouthindependent.org.

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