Giving new definition to irony, Rob O'Leary's academic pedigree in the spirited arena of Boston politics reads like one from central casting: Kimball Union Academy in New Hampshire; The School of Foreign Service at Georgetown University where he rubbed shoulders with a young Bill Clinton; a master's in public policy from Harvard; and a PhD in history from Tufts. The state senator serving Cape Cod and the Islands, with his trademark Kennedy good looks, was the first Democrat to represent the region in the state Legislature since the Civil War. He now seeks bigger fish to fry - by replacing retiring Congressman Bill Delahunt in the state's 10th Congressional District.

The 64-year-old Boston native, who now lives in Cummaquid, learned the rule of the streets at an early age, hanging out with his older brother, Jim, now a district court judge, and his brother's best friend, Paul Tsongas - the former congressman, U.S. senator, and presidential candidate, who died of cancer in 1997. O'Leary likes to tell the story of the day his brother and Tsongas took the board exams to enter law school. Tsongas, as the story goes, turned to his brother and said, "Jim, I screwed around for four years at Dartmouth, and I'm going to make it up now in four hours!"

O'Leary, by his own admission, followed suit in a sort of self-redemption, although his learning curve was more elliptical and his rebound longer than a few hours. Early on, O'Leary's academic record was about as impressive as "Big Papi's" batting average of late. A lot of whiffs. "I lost my way," O'Leary says candidly, noting he never took schoolwork seriously until his senior year at Georgetown. "I then had to repair my academic record." Short of expunging it, his only option was graduate school, he concluded.

Such lackluster performance might have forced a lesser man out of educational circles, but not Robert Aiden O'Leary, who went on to become a longtime history professor at the Massachusetts Maritime Academy. With all due respect to his humble posture, his intellect and street smarts propelled him forward-sprung from a sturdy family tree with roots reaching back to West Cork and Sligo.

O'Leary's paternal grandfather, James, a first generation Irish American from West Cork and a man with a penetrating Irish accent, labored as a bellhop in Boston in providing for his six children. O'Leary's paternal grandmother, Bridget (McMann), a charismatic individual who commanded respect at first sight, raised the family in humble surroundings in the South End, not far from where the Boston Herald now sits on Harrison Avenue. Their children did well: O'Leary's father, Dan, was a college president with triple degrees from Boston College; Uncle Jim was a well-known surgeon; Uncle Tim was the No. 2 man in the Boston Department of Public Works; Aunt Helen was head of nursing at Boston City Hospital; Aunt Marguerite was a respected businesswoman; and Uncle Connie, an Air Force pilot who was shot down and killed over New Guinea in World War II, grew up as best friend to Maurice Tobin, the former mayor of Boston, governor of Massachusetts, and Secretary of Labor under Harry Truman.

Talk about overachievers. And their work ethic was passed down to the next generation. "It's a classic Irish family," says O'Leary, self-deprecating in his assessment of himself. "I was the trouble maker, a complete screw off at times, the guy you tried to save from landing in a homeless shelter," he recalls in jest.

Hardly the case; such hyperbole likely masks a family pecking order-common with the Irish. While O'Leary's attention span may have failed him at times, the family genes triumphed over hasty missteps.

O'Leary's father, now deceased, and his mother Marguerite (Moriarty), who grew up in South Boston and lives in South Yarmouth, also raised six children of impressive note. In birth order: Nancy is a retired school principal; Jim is the judge, a Dukakis appointee; Dan is a neuro-radiologist and president of Carney Hospital; Ellen is a retired schoolteacher; and Debbie, an "Irish twin" born the same year as O'Leary, is a successful real estate broker.

Large families often relegate modesty to the bottom rungs, but O'Leary over time learned to persevere and was blessed by a vision, brought on by a lesson his parents taught him: devotion to the cause of others.

O'Leary's father was a cerebral type, a history professor, who read a book a day. "He was totally committed to education," says O'Leary, who lived in Roxbury's Egleston Square until he was eight, then moved to Lowell. "He was also very political. I'm probably a lot like him. Dad could be strict, every once in a while coming down on us like a ton of bricks, but he also let out rope in our teenage years, allowing us to learn from our mistakes."

The elder O'Leary attended Boston College High School, Boston College, then Boston College graduate school where he earned a PhD in history. He taught history for many years, later becoming president of Lowell State College. He was influential in the school's transition to the University of Lowell, becoming its first chancellor. Today the school is part of the University of Massachusetts.

Dan O'Leary met his future wife, Miss Moriarty, in the classroom as a young high school teacher in Boston. Years later they re-connected on Carson Beach during the summer, developed a relationship, and got married. More pragmatic than her bookish spouse, she was the disciplinarian of the family. "She could be strict," says her son during in an interview recently on the campaign trail. "With all those kids going in different directions, she ran that family at times like the Marine Corps. But she is very caring and there's a shyness to her."

O'Leary inherited his appreciation of history from his father and his sense of caring from both parents. But growing up in Lowell, he didn't distinguish himself in the classroom or on the playing fields-attending Oakland Elementary School, Moody Junior High School, and Keith Academy, a high school then run by the Xaverian Brothers.

"I wasn't much for sports," he says. "I played some tennis, and I tried out for varsity basketball as a guard. I was one of those kids they put on the junior varsity when you were a senior."

In school, O'Leary indeed was on cruise control, gazing out the window as the course work passed him by. And so his dad sent him to a year at the venerable Kimball Academy in Meridan, N.H., established in 1812 by the Council of New England Churches to assist in "the education of poor and pious young men for the gospel ministry." The father was just hoping the son would get religion in the classroom. Some of it took, enough at least to get him into Georgetown where he absorbed the culture.

In O'Leary's freshman year, he was helping a friend run for class president. "I was walking to class one day, and a guy comes up to my friend and starts talking to him," O'Leary recalls. " ‘Who's that,' I asked after the conversation. "Oh, that's just my opponent," his friend replied. "I'm going to kill him in the election."

The opponent was Bill Clinton, and the election result was what you would expect, but for Rob O'Leary, it was a baptism in politics and life in general.

"Bill Clinton," he says, "was smooth as silk, and the women loved him. I sat in class with him, and he was very glib, and exceptionally bright. He was the kind of guy who was on a first name basis with the president of the school a week after he arrived, while the rest of us were trying to figure our class schedules. He had so much talent he could make it all work."

Making it all work finally sunk in with O'Leary, who began turning his attention in his senior year to a game plan for the future. Certainly no Robert Frost who took the road less traveled, O'Leary followed in his father's footsteps, where he discovered the light of success.

After Georgetown, O'Leary taught in the public schools and at the Massachusetts College of Art, served in the Army Reserve, and worked on his graduate degrees. He then taught history and politics at the Massachusetts Maritime Academy in Buzzards Bay where he is a tenured professor today. He also is an adjunct professor at Cape Cod Community College.

O'Leary, now divorced, moved to the Cape in the early 1970s, after spending summers there as a youth. He has three daughters - Christine, a special education teacher; Katherine, an attorney; and Nicole, still in school on the Cape. He also has four grandchildren.

O'Leary's segue into politics was more out of a desire to serve than anything else. His passion was teaching. Always.

He joined the Barnstable Civic Association and became its president, then in 1987 won election as a Barnstable County Commissioner. He was instrumental in reorganizing county government on the Cape and in creating the Cape Cod Commission, the regulatory land use agency. In 2000, he won election to the State Senate, replacing Republican Henri Rauschenbach, who had been appointed to a post in the Jane Swift administration.

Asked how his late father would have felt about the election of his prodigal son to the state Senate after years of directing, almost herding, him toward more productive circles, O'Leary paused. "I've never been asked the question," he says in an emotional moment. "I think my dad would have been proud. I think he would have been quite pleased. I regret he was not there to see it."

Since his election, O'Leary's work ethic has been in overdrive and he is considered to be among the most productive members of the Senate. He is Senate Chairman of the Joint Committee on Education and Senate Vice Chairman of the Joint Committee on State Administration & Regulatory Oversight. Earlier this year, he was intimately involved in passage of the Education Reform Bill, the state's first major piece of education legislation in 16 years. He also played a key role as a sponsor of the Ocean Management Act, the first in the nation to zone state waters for offshore renewal energy uses.

In many ways, Rob O'Leary is an example of the redemptive potential in all of us, an everyman who persevered and found the handle on his God-given gifts. A personal role model was Ted Kennedy; the two were friends, working closely together on Cape and Islands issues. "What was striking about Ted Kennedy is that the older he got, the better he was," says O'Leary. "He was more on track, more energized. I always loved that quality in him. He was full speed ahead, right up until the end. He made his share of mistakes, but he never quit. I have tremendous admiration for that."

A long distance runner, who still covers five miles a day when his schedule allows, O'Leary finds comfort in Kennedy's legacy later in life. The senator also taught O'Leary the need to reach across the political aisle for compromise where appropriate. "You never accomplish anything on your own," O'Leary says. "It's a collective effort at all levels. You always have to be willing to give credit to others."

Every day now, O'Leary sets his sights on a winning course for his congressional race. While he won't admit it, he appears driven to show his father that all the angst and instruction were worth it. "I wasn't waiting for this opportunity to happen, although I always had it in the back of my head" he concedes.

Now when the starting gun in life goes off, O'Leary sprints. He never looks back. So don't be surprised if he sets records.

Greg O'Brien is editor and president of Stony Brook Group, a publishing and political/communications strategy company based in Brewster. He is the author/editor of several books and contributes to several publications.