FULL CIRCLE: Good Sense and Smart Choices

CM YEARS 

The one and only scholarship awarded in 1960 by the local chapter of the Knights of Columbus helped Jack Cleary ’64, a West Roxbury native, attend the relatively new school in his neighborhood. “My dad worked in the post office and so obviously we had no money,” recalls Cleary. What he knew about Catholic Memorial was only what he’d heard from his peer group. What he experienced upon arriving was “…the brothers were pretty demanding, and in some cases, frightening. That was back in the days when you’d pay a real price if you misbehaved,” says Cleary. But what stood out most of all was the athletics. “I did well academically, but that wasn’t my primary focus,” he says. “My primary focus and source of satisfaction was playing on the basketball and baseball teams and interacting with Mr. Perry (CM’s first athletic director), who had significant influence on me as a mentor and role model.” Perry, as well as Brother Tom Feerick, who “was Perry’s assistant coach—and just a wonderful human being,” adds Cleary, were turning CM’s basketball program into a powerhouse. And in turn, Cleary found a meaningful role, playing on the varsity team in both his junior and senior years and reaching the Tech Tourney Championship the year he graduated. The oldest of three, (his brother Steve followed him to CM two years later), Cleary would be the first in his family to go to college. “Early on in my life that was a foregone conclusion,” he adds. He applied to Notre Dame, Boston College, and a few others, including MIT. “It was my grandmother who said, ‘You’re good at math, you should apply to MIT.’” Acceptances along with scholarships arrived, but Cleary chose MIT because he could live at home. “At Notre Dame, I would have had to pay for room and board. So, I chose MIT.” 

As luck would have it, Cleary and a fellow Knight, Harry Anderson, both of whom had been members of what was called the “Brain Room” for the top learners at CM commuted together to MIT each day. They were among the very small percentage of MIT students who were commuters. At CM, Cleary focused on sports and then academics. At MIT, that flipped. “I remember walking down the long corridor that runs from 77 Mass. Ave. with Harry early in our freshman year and saying, ‘I think I understand what’s going on in humanities so maybe I can get an A. Calculus isn’t too bad, so hopefully a B. Chemistry is pretty terrible so maybe a C. And physics is awful so that could be a D.” That first year was the hardest thing he’d ever done. But it taught him that he could accomplish difficult things. What’s more his actual grades far exceeded his initial predictions which he puts down to hard work, and the preparation CM had provided him. “I think the study skills, the discipline and the commitment to do it right and succeed was what motivated me.” And while he played intramural basketball and two years of varsity baseball, Cleary had something more important to focus on. “By the time I was a junior, I started dating the woman who I’m married to today. We got married a week before graduation. And at that point, I had applied to graduate schools in economics, and I decided to go to Yale.” By his second year at Yale, Cleary realized he needed to change course. His wife suggested he go to law school. That’s what he did, attending Harvard Law School and setting a course for his professional future. Upon graduation in 1974, he joined the Boston law firm of Goodwin, Procter. 

As luck would have it, Cleary and a fellow Knight, Harry Anderson, both of whom had been members of what was called the “Brain Room” for the top learners at CM commuted together to MIT each day. They were among the very small percentage of MIT students who were commuters. At CM, Cleary focused on sports and then academics. At MIT, that flipped. “I remember walking down the long corridor that runs from 77 Mass. Ave. with Harry early in our freshman year and saying, ‘I think I understand what’s going on in humanities so maybe I can get an A. Calculus isn’t too bad, so hopefully a B. Chemistry is pretty terrible so maybe a C. And physics is awful so that could be a D.” That first year was the hardest thing he’d ever done. But it taught him that he could accomplish difficult things. What’s more his actual grades far exceeded his initial predictions which he puts down to hard work, and the preparation CM had provided him. “I think the study skills, the discipline and the commitment to do it right and succeed was what motivated me.” And while he played intramural basketball and two years of varsity baseball, Cleary had something more important to focus on. “By the time I was a junior, I started dating the woman who I’m married to today. We got married a week before graduation. And at that point, I had applied to graduate schools in economics, and I decided to go to Yale.” By his second year at Yale, Cleary realized he needed to change course. His wife suggested he go to law school. That’s what he did, attending Harvard Law School and setting a course for his professional future. Upon graduation in 1974, he joined the Boston law firm of Goodwin, Procter.