Chesapeake sheriff’s second-in-command steps up


Col. Jim O'Sullivan stood behind a lectern, eight inmates at a table before him feasting on fried chicken and baked beans.

"It's really important what we've learned in the last 12 weeks," he said to those who came to see the graduation of the Bible study class held this summer.

"You see we have an overcrowded facility," he told the inmates. "You see how hard it is to get a job. I've made bad decisions in my life. I don't cast any stones."

Sounding a bit like a preacher, he implored them to better their lives. To take the biblical lessons they'd learned and share them with fellow inmates.

"Thank you very much for what you've done here today," O'Sullivan told them.

"Thank you, Sheriff," said the jail chaplain, Britton Joyner.

"Sheriff-in-training," said O'Sullivan, chuckling as he slipped back into his seat.

Sheriff O'Sullivan?

Not technically. But he has largely been playing the part since April, when Sheriff John Newhart announced he was stepping down Oct. 1.

O'Sullivan's role has become more active since Newhart was elected to his 11th term three years ago and gave O'Sullivan more responsibility.

O'Sullivan's rise began long before Newhart contemplated retirement, long before O'Sullivan began building a campaign war chest and long before he became one of the highest-ranking members of the sheriff's office.

When he takes over, O'Sullivan won't simply be stepping into a position of power. He will be taking over a 42-year legacy.

When Newhart was first elected in 1969, Chesapeake was 6 years old; it turns 50 in January. He was the youngest sheriff ever elected in the state and the first Republican voted into any office in Norfolk County since the Civil War. Today, only two other sheriffs in the country have served longer.

Either through a special election or the general election in November 2013, O'Sullivan, a Republican, will have to prove to voters he's worthy of keeping his new title. He's been in campaign mode since mid-2010 and has amassed $102,494 in his campaign fund.

His challengers could face an uphill battle.

"I said all along when Sheriff Newhart decides to retire, I don't think anybody could take his place but Jim O'Sullivan," said Mary Lou Hill, president of the 148-member Niners Senior Citizen Club, one of the most active senior groups in the city. "He has the greatest interest in the seniors as anybody I've ever seen except for Sheriff Newhart."

It won't be an easy year. O'Sullivan's first big challenge surfaced in June, when an auditor found that three temporary jail buildings that were supposed to relieve an overpopulated jail not only grossly exceeded budget, but also were not approved by the state before being built. As a result, they aren't being used to house inmates.

It's a sticky predicament, one that could potentially cost taxpayers more than $7 million if it's not resolved.

The sheriff's office is in the business of housing inmates, not building jails or approving contracts for them. But in 2008 - long before the temporary housing was built - O'Sullivan, acting on Newhart's behalf, helped convince the city that jail overcrowding was an emergency situation. He supported Newhart in his recommendation that the city use Proteus On-Demand, the company that ended up building the facilities.

As City Council members and the mayor learned the audit's finding, the finger-pointing began. In August, state police were brought in to investigate.

O'Sullivan said he believes they won't find fault in him or the office.

He's also pledged to spend whatever time and energy is needed to lobby legislators for changes that would allow him use the temporary buildings.

"As the new sheriff in town, I'm going to focus on the future and what we can do to rectify the situation," O'Sullivan said. "I really feel up to the task."

In Chesapeake, the sheriff's office does more than just run a jail, handle court security and serve papers. Its involvement in the community transcends law enforcement.

Its most visible symbol for decades has been Newhart.

The sheriff has made his name synonymous with senior citizens. The South Norfolk native has two annual events to benefit them - the Great American Food Fest and the Senior Support Services Seminar.

Money raised from the Food Fest helps fund a program for seniors whose homes are burglarized. It pays for new locks or whatever assistance they need. Newhart also started a program where volunteers check on seniors who live alone.

O'Sullivan, 46, will inherit Newhart's influence, his supporters and his senior programs. But he plans to leave his own mark - by focusing on children and young adults.

As a father of three, it makes sense. O'Sullivan has a 23-year-old son, Dillon, from a first marriage; 15-year-old son, Jake, and 13-year-old daughter, Kasey, from his second marriage, to police Officer Kelly O'Sullivan. He is currently married to Jenny O'Sullivan, a jail lieutenant.

Three years ago, O'Sullivan started an umbrella group that runs five programs for children. One involves deputies mentoring 10- to 14-year-olds, while another prepares high school girls for college. In addition to his three-day football camp, there's an anti-bullying campaign that 7,500 kids participated in last year.

"He's stepped up in a big way in the community, creating programs that really go to the heart of the issues in the city," said Steve Best, former Chesapeake fire chief and O'Sullivan's friend. "They actually work."

Like Newhart, O'Sullivan became committed to the community from growing up here.

O'Sullivan was born in Maryland, the youngest of four boys. His parents split when he was 1, and his mother raised her sons in Virginia Beach, near Bow Creek Golf Course.

After eighth grade, O'Sullivan moved to Boulder, Colo., to live with his father. He went to high school there and got a basketball scholarship at Adams State University, where he played for two years.

His scholarship covered only tuition - not room and board - so on summer breaks, he would return home to frame houses for his oldest brother's company. His hoop dreams ended a week before his junior year, when his right index finger was caught in a forklift and severed in half.

Instead of finishing school, O'Sullivan stayed here. At 21, with a baby on the way, he decided to pursue his dream of becoming a law enforcement officer. He met Newhart at an event and later sat down with him to discuss his future. O'Sullivan had just moved to Chesapeake and wanted to begin - and finish - his career here.

Newhart didn't have any job openings, but he liked the 6-foot-6 O'Sullivan, whom he fondly refers to as "the short guy."

"You go on down and talk to Sheriff (Frank) Drew (in Virginia Beach) and see if we can work something out," Newhart said. Newhart called Drew and told him about O'Sullivan. Newhart also warned Drew not to get attached.

"I'm going to bring him back here," Newhart said.

Less than a year after Drew hired him as deputy in 1991, O'Sullivan was back in Chesapeake working for Newhart.

"You could spot a natural leader," Newhart said.

In June, O'Sullivan's skills were put to the test.

First, an inmate escaped from jail. Then, a city auditor's report revealed that the $7.2 million temporary jail buildings were not being used.

O'Sullivan, the undersheriff,

told Newhart the inmate got out on his watch, that the jail was his responsibility and that he'd handle the aftermath. Within a week of the escape, two deputies were fired and others disciplined, and O'Sullivan went about capturing the escapee.

"That's why I like him," Newhart said. "He took care of it."

With staff stretched thin and morale in jeopardy, O'Sullivan also showed his compassionate side, going to the jail shortly after the escape to give a pep talk.

"I walked through the whole jail and told every person they're doing a fantastic job and I'm proud of them," O'Sullivan said. "This is a bump. We're going to take appropriate measures and forge ahead. You don't shy away and wait for it to pass. You gotta hit it head on."

When O'Sullivan takes over as sheriff, he'll inherit an office with more than 400 employees, a $35 million budget that has endured $2.3 million in budget cuts in the last three years, and a jail holding more than twice its capacity of 543 inmates. And then there are the temporary jail facilities.

His 20-year career may have prepared him for the challenges. After he became a deputy, O'Sullivan rose quickly through the ranks, serving in just about every capacity: corrections, booking, court bailiff, public information, internal affairs and background investigations.

While at the sheriff's office, O'Sullivan got back to his education, combining classes from St. Leo University, Tidewater Community College and Bluefield College to earn his degree in behavioral science.

"I tell my children all the time it's a lot easier to do it (right) out of high school," he said, pointing to the framed copy of his degree on the wall of his office. "I really appreciate my degree, and I don't take it for granted."

Thirteen years after he was hired in Chesapeake, O'Sullivan was promoted to lieutenant. O'Sullivan skipped captain and went right to major in charge of administration, which meant he was in charge of the budget, employees and training.

O'Sullivan had never prepared a budget, and he went to the former fire chief, Best, for help.

"He is an extremely quick learner, a very bright individual," Best said. "I saw right away there were traits with Jim - he was destined for a greater level of responsibility."

He served as major for two years before being promoted to chief deputy. Two years ago, he became the undersheriff.

"I really wanted someone I could trust who was going to do the right thing for the department and the right thing for the future of the sheriff's office," Newhart said.

The future. For O'Sullivan, there's the immediate future, and there's the rest of his career.

Chesapeake isn't a stepping-stone to a bigger city or higher office. Like Newhart, he plans to retire here. As sheriff.

His immediate goal is to make the jail project right, to get the OK to use the temporary buildings for inmates.

Although some have declared that there's no way the state will approve them. O'Sullivan said the buildings serve one purpose: to house more than 200 inmates with the least amount of time to serve and who are easing their way back into the community.

He recently met with the state's Department of Corrections to discuss what bureaucratic barriers need to be cleared. He says he'll work with legislators to make it happen.

"If we don't put inmates in those buildings, we have failed," he said, sounding a lot like the new sheriff in town.

Veronica Gonzalez, 757-222-5208,

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