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Donald Fred 'Lefty' Files, 75
CAPE ELIZABETH -- Donald F. Files, 75, died on Feb. 16, 2013, at Maine Medical Center, due to complications from a stroke, with his wife and sister, Barbara Files, by his side.
He was born in Gray on Dec. 26, 1937, the son of John and Hazel Files. Donald was a graduate of South Portland High School, class of 1957.
After high school he attended Washburn University of Topeka, Kan., on a basketball scholarship. He played semi-pro basketball and baseball for the Griffen Club of South Portland. He was the State of Maine President of the Eagles in the 1960s, and a member of the Elk's Club. He was in bowling leagues at the Big 20 in Scarborough, owned and operated Leighton's Express for 27 years, and retired at the age of 50.
Donald was married to Janice Bickford on Sept. 5, 1956. They resided in Cape Elizabeth for over 40 years.
After retiring, he owned and raced horses at Scarborough Downs for about five years. He enjoyed doing canoe trips, including the Allagash River. Donald and Janice built a beautiful log cabin camp on First Roach Pond in Kokadjo where they spent their summers.
Donald enjoyed watching the Boston Red Sox and New England Patriots. He was an avid hunter and loved fishing. He enjoyed traveling on the Amtrak across the United States. He was a man of many stories and loved to talk. He enjoyed spending time with his daughters, grandchildren and great-grandchildren. He was a family man and enjoyed the outsides.
Donald was predeceased by both his parents. He is survived by his wife of 57 years, Janice Bickford Files; four daughters, Judith and her husband Stephen Demo of South Portland, Deborah and her husband Daniel Wood of South Portland, Susan and her husband John Lessard of Goffstown, N.H., and Tammy and her husband Darrell Pettet of Laurel, Del.; 10 grandchildren, Michael Butterfield, Angela Wilder, Christopher Butterfield, Daniel Wood Jr., Andrew Wood, Desiree Demo, Adam Lessard, Erica Lessard, Brent Petett and Cody Lessard; and seven great-grandchildren. He also survived by his sister Betty and her husband Frank McDermott; Beverly and her deceased husband John Coyne; John and his wife Debbie Files; and Barbara Files and her husband Michael Salvagio.
Visiting hours will be held from 4-7 p.m. on Friday, Feb. 22, at the Hobbs Funeral Home, 230 Cottage Rd., South Portland. A memorial service will be held at 11 a.m. on Saturday, Feb. 23, at the funeral home. Online condolences may be expressed at
In lieu of flowers donations
may be made to:
Trout Unlimited, Sebago Chapter
Care of John File
778 Brighton Ave.
Portland, Maine 04102
Published in Portland Press Herald/Maine Sunday Telegram from Feb. 20 to Feb. 21, 2013
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"Janice and family, We are so sad to hear about Lefty's sudden passing. We will miss his presence at..."
- Pat & Cindy Heelan
"Tammy - I just read about your father's passing. Please accept my condolences and know that you and..."
- Dee Fournier
"Janice and Family - Our thoughts and prayers are with you at this time. I have known Lefty his entire..."
- Albert Gilmore
"Janice - Thinking of you and your family at this most difficult time. Lefty will be missed by many...."
"I'm saddened to have read about Lefty's sudden passing. As a youngster growing up in Portland, he was..."
- Tom Ferrante
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