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John James Toffey IV, 85, of Canaan, Conn., writer, teacher and coach at Kent School, Simon’s Rock , and Berkshire School

John loved language, music, and tradition. He kept up his teaching to the very end, offering literature classes on Shakespeare, the Civil War and -- most recently – “Moby Dick.”

John James Toffey, IV died April 1, 2017 in Canaan, Conn., where he had lived since 2015.

A long-time resident of Great Barrington, Mass., John was born May 24, 1931 in Brooklyn, N.Y., to Helen Howard and John James Toffey III. His father’s military service had the family moving frequently, but his roots were firmly in Columbus and Cincinnati, Ohio, where he developed a lifelong passion for Cincinnati Reds baseball and Ohio State football. John attended the Columbus Academy, where he eventually taught, and Phillips Exeter Academy. After Army service in Korea, he graduated from The Ohio State University and received a master’s in English from Columbia University.

His long academic career began at The Kent School in 1958 where he taught English and coached baseball and football. In Kent he met and married Irene Tobin; they and their four children eventually settled in Great Barrington, where John taught at Simon’s Rock Early College. In 1975 he joined Berkshire School and taught English and served in various administrative and coaching capacities until his retirement in 1995.

During a trip to Scotland John became fascinated by Scottish history, particularly the 18th century and the Edinburgh Enlightenment. A sabbatical fellowship in 1992 took him to St. Andrews University, where he delved deeply into “the intersection of the romantic and the rational,” which led to his first book, “A Woman Nobly Planned: Fact and Myth in the Legacy of Flora MacDonald.”

In 1996 John discovered a cache of letters from his father, Jack, to his family back at home during World War II. They were written when Jack was a Lieutenant Colonel serving with the Allied Forces in North Africa and Italy. Inspired, John began meticulously researching his father’s time oversees…tracking down and interviewing people who had served with his father, and working with historians who knew of and had written about him. The product was his second book: “Jack Toffey’s War: A Son’s Memoir,” a personal look at the war from the home front and the lines of battle. Telling this story was John’s passion.

In retirement he and Irene traveled extensively with a particular fondness for the British Isles and Italy. Most important, they treasured spending time with their 13 grandchildren in Kentucky, Cape Cod, Weston, Mass., and northwest Connecticut. They happily attended countless graduations, school concerts and sporting events of all kinds.

In addition to having an encyclopedic knowledge of baseball and brilliant sense of humor, John loved language, music, and tradition. He kept up his teaching to the very end, offering literature classes on Shakespeare, the Civil War and — most recently – “Moby Dick,” perhaps his favorite work of all time.

John was pre-deceased by his beloved Irene. He leaves his children, Hannah (Cameron Peters), John, (Deb), Joseph, and Edward (Katie). He leaves 13 grandchildren who adored him: John, Molly, Claire, Sam, and Will Toffey; Matthew, Megan, Daniel, and Annie Toffey; Connor Toffey; and Caroline, Chloe and Dexter Peters; two great-grandchildren: John James Toffey VII and Finley Irene Stone; sisters Anne Cushman and Barbara Bonner, dear friend Sally Brooke, as well as many nieces, nephews, brothers and sisters-in-law, and many inspired students.

Calling hours will be at the Newkirk-Palmer Funeral Home, 118 Main Street, Canaan, Conn, on Monday, April 10 from 6 – 8 p.m. A funeral service will be at the Kent School Chapel in Kent, Conn., on Tuesday, April 11 at 11 a.m. Burial to follow immediately in Kent School Cemetery.

In lieu of flowers, contributions in John’s memory can be made to Geer Village Senior Living or Housatonic Valley Regional High School Athletics.


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Teresa Mae Kosberg, 89, formerly of Great Barrington

A memorial celebration will be announced at a later date.

Michael Filmus of Great Barrington

Services will take place at the Elmwood Cemetery in Great Barrington.

Andrew Russell Humes, 66, formerly of Great Barrington

A memorial will be held on Saturday, September 7, at the John P. Humes Japanese Stroll Garden and the Tavern House at the Humes Preserve headquarters in Mill Neck, N.Y., Andrew's childhood home.

The Edge Is Free To Read.

But Not To Produce.