Robert M. Flanagan

Robert Michael Flanagan passed away peacefully on December 8, 2023, surrounded by family, after a year-long illness. Bob was 79 years old.
Born February 5, 1944 in Memphis, TN, Bob grew up in South Orange, NJ, with his brothers Jack and Dave, and sister Mary. His mother, Helen Froehlich Flanagan, was a retired school teacher from Glen Ridge, NJ. He graduated from Columbia High School and then followed his father, John J Flanagan and attended Georgetown University, graduating with a BSBA in finance in 1967.
Bob was a life-long lover of Georgetown, serving on the Board of Regents and was awarded the prestigious John Carroll award in 2014. While at Georgetown, he became a member of The Georgetown Chimes acapella group where he joined, what turned out to be, lifelong friends and brothers.
Most importantly, at Georgetown, he met the love of his life, the beautiful lass from Marblehead Mass, Maurie McIntire. After graduating, Bob enlisted in the army and served two years of active duty including 14 months in Korea.
Following the army, Bob and Maurie were married on July 19, 1969, at Our Lady Star of the Sea in Marblehead, MA and then moved to NJ. He started a long career on Wall Street becoming a partner at Spear, Leeds & Kellogg and later managing partner at Lawrence, O'Donnell, Marcus & Co., a specialist firm. Bob was a talented floor trader at the NY Stock Exchange where he held a seat until his retirement in 1999.
Besides his love of career, Bob was an avid racquets player. He spent many a day on the tennis and paddle courts. He and his paddle tennis partner were nationally ranked. He was the President of Orange Lawn Tennis Club from 1979-1981.
Bob had a love-hate relationship with the game of golf and spent many years honing his craft on the driving range, but it was a long walk to the first tee. However, he was very generous with his playing partners, frequently offering new swing thoughts, sometimes on the tee.
Some of his fondest memories were spent on the links in Ireland with his family and friends, especially in the pubs afterwards singing Irish folk tunes and having a pint or two.
Bob and Maurie have been lucky enough to be active members in the wonderful communities within Kiawah Island, South Carolina, El Dorado in Indian Wells, California, and especially, East Chop in Oak Bluffs, Martha's Vineyard, where they have called home since 1990.
Bob was blessed with so many gifts, including a deep and sustaining faith, but the most important thing to him, and his proudest accomplishment, was always and will forever be his family: his loving wife of 54 years, Maurie, their three children Joe, Sean and Mara and 11 grandchildren. Joe and his wife Maura and their 6 children: Mary, Dottie, Annie, Jojo, Freddie, and Owen. Sean and his wife Sally and their three children: Molly, Charlie, and Neve. Mara and her husband Kevin and their two children: Lacey and Sam.
He was what the Celtic heritage referred to as an Anam Cara, a "soul friend." No pretense, only honesty. He could look into your soul. And he let you look into his. He was loyal beyond words and generous beyond measure. He will be deeply missed by his family and all those who were lucky enough to call him friend.
Services will be held on Saturday, December 16 at 11:00 am at St. Augustine Church, 56 Franklin St, Vineyard Haven, MA and burial will follow in Sacred Heart Cemetery, Vineyard Ave, in Oak Bluffs. All are welcome. In lieu of flowers, please consider making a donation in his memory to Martha's Vineyard Community Services or Harbor Homes.