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Shelter Island Reporter obituaries: Osofsky, Sprague

Meyer ‘Mike’ Osofsky
Meyer “Mike” Osofsky, a resident of Shelter Island for five decades, passed away peacefully on Wednesday, Oct. 30. He was 95.

Mike was born on July 23, 1924, in Brooklyn. His parents, Harry and Jenny (Goldstein) Osofsky were Jewish immigrants from Eastern Europe who arrived in New York City at the turn of the century. The second-born of eight children, Mike attended James Madison High School, where he charmed his future wife, Aileen, in their radio production class.

He played for the school basketball team and worked as a soda jerk (later he fondly recalled his mother reminding him until the end of her life about “the time he was a jerk”).

After graduating, he worked as a welder in the Brooklyn Navy Yard until being drafted into the United States Army Air Corps.

During World War II, Mike served as a member of the 451st Bombardment Group. A waist gunner on a B-24 bomber, he flew 31 missions over enemy territory, parachuting into American-controlled Italy after his plane was brought down by engine failure. When he returned to the United States in 1945, he was discharged with a rank of Technical Sergeant.

All who knew him enjoyed the war stories he would tell at every opportunity — reminding younger generations that army life had been his higher education, and that serving was the great honor of his life.

Upon returning from the war, Mike and Aileen were married and he founded a women’s wear company named for her. Popular in the postwar years, “Aileen” was publicly traded on the New York Stock Exchange. Mike retired from the company in 1978.

Mike and Aileen first came to Shelter Island in the late 1960s. Falling in love with Hay Beach, they decided to build their dream home there alongside their friends, the Jacobs and Seidler families. Mike and Aileen selected architect Norman Jaffe, who designed all three homes. The Osofsky House is considered one of Jaffe’s signature achievements; all three were featured in the 2005 Parrish Art Museum retrospective of Jaffe’s work.

Mike and Aileen were longtime members of the Gardiner’s Bay Country Club and, along with their daughter Randy, owners of the Manhanset Chapel. In 1986, the family donated the building to the Shelter Island Historical Society.

In addition to spending summers on the Island, Mike was a longtime resident of Phoenix, Ariz. and New York City. Mike spent his later years devoted to his wife and family and to philanthropic efforts.

Aileen died in 2010 and made Shelter Island her final resting place.
Mike is survived by his brothers Herman and Joseph and sister Annette; his children, Larry and Wailin Osofsky, Randy Osofsky and Steve Kessler, and Alan and Deirdre Osofsky; his grandchildren, Anna Osofsky and Alex Rochios, Zachary and Leigh Osofsky, LuLing Osofsky, Judd Kessler and Ilana Turko, Dean and Juliana Osofsky, Ryder Kessler, and Jarema Osofsky; and seven great-grandchildren.

Mike’s ashes will be interred beside those of Aileen — the true love of his life.

Dering John Sprague
Dering John Sprague, 84, of Lawrenceville, N.J., a direct descendant of Nathaniel Sylvester Dering, passed away on Saturday, Nov. 2, 2019 at Greenwood House, after a short illness. He died peacefully, with his children at his side.

He was born on Sept. 30, 1935, in Mineola to Dering Jay and Gertrude Alice Sprague. He graduated from high school from St. Peters Prep in Jersey City, N.J. and graduated from college with a BA, and then an MBA, from Fordham University’s School of Business. He served in the United States Army as a first lieutenant.

Dering worked as a certified public accountant for KPMG and Freeport McMoran, and later specialized in internal auditing. In the 1980s and 1990s he worked as an auditor for K. Hovnanian, and eventually, Toll Brothers Inc.

An enthusiastic fan of classical music, he collected recordings of Arturo Toscanini. Dering was also an avid reader, with Lewis Carroll’s Alice’s Adventures in Wonderland among his favorites.

He was married for 34 years to Maureen Anne Sprague, who passed away in 2009; she was the daughter of Arlene and Joseph Miller, of Staten Island. As a couple in the 1980s, they enjoyed being season ticketholders at the New York Philharmonic, and made a point of sharing the joys of music with their son and daughter.

He was a member of St. Mary’s Church, Colt’s Neck, N.J., where he served for nearly 30 years on the lector staff. He also taught as part of a bible study group.

Dering is survived by his son, Dering Joseph Sprague and his partner Barbara Campbell, and his daughter, Catherine Noëlle Sprague and her husband Matthew Bisanz. He is also survived by his sister, Sharon Ballard Sprague, and numerous nieces and nephews.

At the request of the family, donations can be made in his name to The National Multiple Sclerosis Society.

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