The night after Labor Day in 1996, David Hobson and two buddies spray-painted graffiti on as many as 10 businesses in downtown Sanford.

Shortly before 2 the next morning, Hobson was arrested in a church parking lot while trying to run away. He was charged with criminal mischief.

He was 18, and starting a long involvement with Maine’s criminal justice system. Hobson, who will turn 34 on Wednesday, has been arrested 10 times since that incident.

While awaiting trial on burglary charges in New Hampshire, he escaped Thursday afternoon from the Carroll County House of Corrections in Ossipee, going over a fence topped with razor wire. Police were still searching for him Monday.

Jason Johnson, superintendent of the jail, said Hobson is the first inmate to escape since the facility opened in 2003, and only the second in Johnson’s 15 years on the job.

Hobson grew up in Alfred and spent four years at Massabesic High School with the class of 1996. According to school officials, he failed to complete the requirements for his diploma before leaving Massabesic.

For the graffiti incident, he got a 90-day jail sentence with all but 48 hours suspended. He was given a year’s probation and ordered to pay restitution of $1,000.

In 2002, Hobson was arrested for disorderly conduct. He pleaded guilty and paid a $75 fine.

Three years later came the first in a string of felony charges for burglary. Hobson broke into cars and homes and stole cash, electronic equipment and DVDs in Alfred, Acton and Lyman.

He was convicted in May of 2006 and sentenced to a year in jail, ordered to pay restitution of $7,114 and given three years’ probation. He subsequently violated probation four times, in 2008, 2009 and twice this year.

He spent a second year in jail, including most of 2009, after being found guilty on a drug charge.

In April of this year, Hobson was charged with felony theft, and in August he was sentenced to another year in jail. In early October, he was transferred from the Maine Correctional Center in Windham to the jail in Ossipee to face burglary charges in New Hampshire.

In 2004, before any of his felony arrests, Hobson fathered a daughter with a woman from Kennebunk. Last summer, Hobson fathered a son with Christy Wanager of Biddeford, who is listed as a co-defendant in the New Hampshire burglary case. Court records also give her hometown as Goffstown, N.H.

Although Maine State Police consider Hobson armed and dangerous, Wayne Rufus does not. He knew Hobson as a childhood classmate, a rambunctious kid who enjoyed baseball and basketball and gave Rufus’s parents fits on a school field trip to the Museum of Science in Boston.

“We were in the same grade all through elementary school and all through junior high until about sophomore year,” said Rufus, who moved from Alfred to Sanford after graduating from Massabesic in 1996.

More than 20 years ago, Hobson raced up and down the museum’s escalators, much to the frustration of Rufus’s parents, chaperones who tried in vain to keep him with the rest of the group. “He gave my dad a handful that day,” Rufus said.

Hobson didn’t get into serious trouble until high school, Rufus said. They played sports together and hung out in the summer.

“He was just a normal kid back then,” said Rufus, who remembers Hobson as a second baseman and right fielder in baseball and a point guard in basketball, good enough to make town all-star teams in both sports. “He has good parents and a good sister. I was really good friends with his sister as well.”

Hobson’s sister, Jenny Lane, declined to comment Monday when reached by phone.

His father, Glenn Hobson, was arrested Friday night by state police and charged with hindering apprehension and refusing to submit to arrest.

Steve McCausland, spokesman for the Department of Public Safety, said troopers found medical supplies, food, water, clothes and blankets that had been left outdoors near the father’s house in Alfred.

The elder Hobson has a criminal record, having pleaded guilty in 2005 to a misdemeanor charge of assault and paying a fine of $200.

Rufus said he has lost touch with David Hobson in the last 15 years.

“I knew he had trouble a couple years ago and I talked to his sister and they were trying to help him stay out of trouble,” Rufus said. “But then, I don’t know what happened with the robberies and everything he did.”

Staff Writer Glenn Jordan can be contacted at 791-6425 or at: gjordan@pressherald.com