Robert Michael Flanagan passed away peacefully on Dec. 8, 2023, surrounded by family, after a yearlong illness. Bob was 79 years old.
Born on Feb. 5, 1944, in Memphis, Tenn., Bob grew up in South Orange, N.J., with his brothers Jack and Dave, and sister Mary. His mother, Helen Froehlich Flanagan, was a retired school teacher from Glen Ridge, N.J. 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 lifelong 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 a cappella group, where he found 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, and then moved to New Jersey. 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 N.Y. 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 to 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 of time spent on the links in Ireland with his family and friends, especially in the pubs afterward, 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, S.C., El Dorado in Indian Wells, Calif., and especially East Chop in Oak Bluffs, Martha’s Vineyard, which they have called home since 1990.
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.
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 have six children, Mary, Dottie, Annie, Jojo, Freddie, and Owen. Sean and his wife Sally have three children, Molly, Charlie, and Neve. Mara and her husband Kevin have two children, Lacey and Sam.
Services will be held on Saturday, Dec. 16, at 11 am at St. Augustine’s Church, 56 Franklin St., in Vineyard Haven, and burial will follow in Sacred Heart Cemetery on Vineyard Avenue, 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 to Harbor Homes.
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