Robert H. Reilly

Robert H. Reilly, “Bob”, 82, of Marblehead, MA, passed away peacefully in his home surrounded by family on July 8th, 2023, after a long and hard-fought battle with Alzheimer’s disease and cancer. Bob was born, along with his identical twin brother John, on May 27, 1941, in Newton, Massachusetts to John A. and Viola Reilly. At the time of his birth, he weighed 1.5lbs and was not expected to live, but amazingly survived and was subsequently named after the doctor that saved him. A few years later, his sister Paula Horner (Reilly) was born and remained a close friend and confidant throughout his lifetime.

Bob’s life was dramatically altered when his father died unexpectedly in his high school years. Recognizing the value of education, which would become a lifetime commitment to his family, Bob worked his way through high school and college to afford tuition while helping his family financially.

He attended Boston College High School and subsequently Boston College (as he would say a “Double Eagle”) where he earned his BA in Economics and went on to a graduate program at Michigan State University to pursue a PHD.

While at Michigan State, Bob was set-up on a blind date with a varsity cheerleader from Elgin, Illinois named Dolly Graening. The Midwestern girl was initially skeptical of the brash Eastern boy’s strange jokes and insistence on the superiority of Brigham’s ice cream, but his persistence and clever wit slowly won her over. Dolly and Bob were married on July 9th, 1966, in her hometown. Dolly remained the love of his life, confidant, partner, and style adviser for 57 years, providing a heroic level of care until the night of his passing.

Bob had many personal accomplishments, but his real love was his family. He was a loving, wise and active presence in the lives of his daughter, Melissa, and his son, Matthew, and subsequently his grandchildren Lachlan, Skylar, and Elsie. In his free time, Bob spent most of his days at a swim meet, water polo match, lacrosse game or baseball game. He was a master of remembering best times, places, statistics and outcomes of most, if not all, of his children’s and grandchildren’s accomplishments. Bob was an avid reader and enjoyed history and keeping up with current events. He was a man of few words at times, comfortable in silence, but always ready to give a fun fact or make a humorous observation. Bob was an amazing speech writer and speaker, which was appreciated and requested frequently by friends and family at numerous celebrations, events and gatherings. His words were always kind but with a fun sense of humor to remind everyone not to take things too seriously, as life is short.

After Michigan State, Bob taught at the University of Connecticut, where he was voted “Professor of the Year” in his first-year teaching. Soon after, Bob made the decision to leave teaching and secured a position in investment banking at Robert Weaver and Associates in Boston. Over the next few years, the family lived in Brussels, Belgium and travelled extensively throughout Europe.

Upon the family’s return to the US and settling down in Marblehead, MA in 1975, Bob was lucky enough to meet what would become his long-term co-founding partners, Charles Downer and Thomas Munnell. They would go on to build a highly successful investment banking firm named Downer & Company. At Downer & Co., Bob was known as smart, honest, loyal, trustworthy, and a quiet but fierce negotiator. Bob had a strong and ongoing commitment to developing the careers of people within the company, stressing the value of integrity and seeking out people who may have taken a unique path to their success. The three founding partners would stay working together for the entirety of their careers until they sold the business to the next generation of partners upon their retirement. In addition, Bob worked very closely with the Fissler Family, helping to source and evaluate venture capital, private equity, and M&A investments. One of the largest and highest profile accomplishments in Bob’s career was writing the business plan for office supply store Staples, which went public in 1989.

Bob is survived by his wife of 57 years Dolly, daughter Melissa, son Matthew, daughter in-law Krista, grandchildren Lachlan Hartshorn, Skylar Hartshorn, Elsie Reilly, twin brother John Reilly, sister Paula Horner and numerous nephews.

There will be a burial service on Monday, July 24th, at Waterside Cemetery in Marblehead at 11am, followed by a reception at the Corinthian Yacht Club from 12-3pm. Please feel free to attend either or both. If you are so inclined, in lieu of flowers, please donate to a charity or organization that is important to you and think of Bob. Fond memories and expressions of sympathy may be shared at www.eustisandcornellfuneralhome.com for the Reilly family.