University Pays Tribute to Robert K. O’Brien ’58

The beloved alumnus, benefactor, and friend is remembered for his leadership, caring, and generosity.

The university’s first major benefactor, Robert K. O’Brien ’58 launched the Next Big Idea, an entrepreneurship competition meant to foster the next generation of business leaders, in 2013. That year, at the very last minute, a sophomore named Derek Canton entered the competition, skeptical that he even had a shot.

Canton went on to win the Next Big Idea, much to his own surprise. An even bigger surprise came when he got a call afterward from O’Brien himself, a business leader and founder of a global company, Health Reinsurance Management Partnership, which along with some 10 other associated companies that O’Brien created, employed more than 300 people. O’Brien had a passion for entrepreneurship, and an even greater passion for supporting talented young people at Worcester State. When he saw potential in someone, he would reach out personally, and over decades he forged many mentoring friendships with Worcester State students.

“Bob personally called to congratulate me and tell me he wanted to invest in the business and take me under his wing,” said Canton ’15, who today is the founder and CEO of Paerpay and one of Forbes’ 2023 30 Under 30 superstars. “I remember literally jumping up and down. Bob was one of the very first people to believe in me. The amount of time and effort he invested in me was priceless. He single-handedly, fundamentally changed my life. That’s where my passion for entrepreneurship blossomed.”

A beloved Worcester State University alumnus and benefactor who touched the lives of many, O’Brien passed away on June 2, 2023, at the age of 88. He and his wife, the late Barbara (Hickey) O’Brien ’57, were among the university’s first major donors, giving nearly $1 million over Bob’s lifetime, even as he committed countless hours of service to the university on various boards. 

“Bob has had an immeasurable impact on Worcester State University,” said President Barry M. Maloney. “He was a cornerstone member of our alumni association, helping us build a culture of philanthropy. More than 100 students have benefitted from his and his late wife Barbara’s scholarships, and several students have started new, successful companies after receiving financial backing via the Robert K. O’Brien Next Big Idea contest. We are truly grateful to have had his engagement and support, and he will be missed.”

O’Brien was born during the Great Depression and grew up in a “cold-water apartment” in Worcester—so named because it offered no hot water. His parents worked hard to provide necessities for the family and passed on their industriousness to their children. In college, he worked two jobs while also taking a full course load. He cooked breakfast at a local diner five mornings a week and drove a taxi every other night, often doing his homework under the dome light of his cab.

Retired Worcester State professor Maureen Stefanini ’58, MEd ’61, EdD went to college with O’Brien. “He worked hard. In the daytime he was delivering for Cushman Bakery. At night he worked for a taxi cab company. He had two jobs and still did well in school. He still managed to get his work done.”

After graduating from Worcester State and establishing himself as an entrepreneur, Bob and Barbara wanted to help hardworking students at their alma mater. In 1997, they established four scholarships in honor of their parents. It was the start of a lifetime of support.

“He was family oriented,” said Stefanini. “They were a good team. They did so much for the college.”

Robert and Barbara O’Brien

Over the years, they established several other scholarships. After Barbara passed away in 2015, Bob created a new endowment for the Worcester State’s Department of Education, honoring her 34 years as a special education teacher in Worcester Public Schools. 

Vice President of University Advancement Thomas McNamara ’94 knew O’Brien for 26 years and considered him a mentor. “He had a great sense of humor,” McNamara said. “He often said he’s failed many, many times—too many to count. But he kept going.” 

When McNamara’s father passed away, O’Brien made a gift to honor him in support of a scholarship McNamara created in his parents’ name. “All my memories come back to him caring about family—my family, too—and doing something for someone else,” McNamara said.

The generosity of the O’Briens reverberated for years. They were the first to establish class year scholarships, which planted the seed for other alumni to do the same. Some of the recipients of one of the O’Briens’ scholarships have, in turn, established their own scholarships.

One such person is Nick Monfreda ’00, who received one of O’Brien’s scholarships in 1997. “It was a true honor and a blessing to have had the opportunity to become acquainted with Bob as both a friend and a mentor over the course of the past 25 years,” Monfreda said. “I was among the first students at Worcester State to receive invaluable financial support from two of the university’s most charitable and compassionate alumni. It is a profoundly selfless act to pay forward one’s own good fortune in order to assist those in need, and Bob’s unwavering dedication to this principle has inspired me to carry on his legacy by endowing a scholarship with the same objective that he and Barbara initiated a quarter-century ago. The aim of this scholarship is to provide aid to students who require some assistance while they work towards completing their studies. Bob will be greatly missed by the Worcester State community, and his legacy will continue to live on.”

In a 2022 interview with the university, O’Brien said it was the students that inspired him to give and support initiatives like the Next Big Idea.

“Worcester State turns out very smart people,” O’Brien said in the interview. “They have as much natural intelligence as any student that goes to Yale Harvard or Brown…. There is a lot of brilliance in the student population—they need to know they have it, and they don’t always know. We need to encourage them to understand that they have all the essentials, and it’s okay to ask for help.”

O’Brien’s generous leadership style also had an impact on those who knew him. “Bob was really good at encouraging but also correcting and giving feedback in a constructive way,” Canton said. “That inspired me in the way that I deal with my employees.”

Robert O’Brien (center, red tie) with President Barry Maloney and winners of The Next Big Idea.

The two kept in touch over the past ten years. O’Brien made a point of calling Canton after the Forbes announcement to tell him how proud he was. “Whenever I think of Bob it brings so much joy to my heart,” Canton said. “He does these incredible things, but he’s not boastful about it. If I live half the life he lived, that would be incredible.”

Another individual whose life was touched by O’Brien’s generosity was Tim Blood ’18, MS ’19, who received an O’Brien scholarship while he was a business major. 

“The scholarship was about industriousness,” Blood remembers. “I had multiple jobs and worked within my community, and it really spoke to me. I got to read the stories of Bob and his family and even got to meet them in person at an alumni donor event. It was an absolute honor to meet Bob and his two sons and give a presentation in front of all the alumni donors about the scholarship and its impact.”

The two kept in touch as Blood went on to work in accounting at TJX headquarters. In March of 2023, O’Brien established the Timothy and Rachel Blood Scholarship for Tim and his wife, who graduated from Worcester State in 2018. With O’Brien’s passing, Blood and his wife are hoping to rename the scholarship in his honor.

“Bob illustrated the importance of good works in donation and putting your time and effort into other people,” Blood said. “He showed me the humility and generosity that a person can have, and he demonstrated that. He put his money where his mouth was, and that is really special.”

O’Brien was predeceased by his wife of 57 years, Barbara Hickey O’Brien; son Kevin R. O’Brien; and parents Arlene M. Lanois O’Brien Knight and Robert Ivor O’Brien. He is survived by his son, Brendan R. O’Brien, daughter-in-law Julie Grasso, and grandchildren Samuel and Gianna; his lady friend, Donna M. Cohen; sister Janet A. Martin and her four children; and trusted friend and colleague Laurie Weil.

Worcester State will hold a celebration of O’Brien later this year.