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Attorney, philanthropist and political activist John L. Colmar rarely saw gray clouds.

“He had an indefatigable optimism, a willingness to always find the silver lining behind any adversity, in the belief that life was a series of exciting opportunities. It was just up to us to take advantage of them if they came along,” said his son Craig. “I don’t think he ever had a pessimistic thought.”

For more than 30 years, Mr. Colmar shared this philosophy through a “holiday inspiration letter” sent to family and friends in lieu of Christmas cards. Several years ago, he self-published a collection of his favorite letters for them.

The one-page letters were treasured for Mr. Colmar’s reflections on life and served as anchors during rough times, to remind his children that “we should not be focused and obsessed with the kinds of everyday nuisances that plague all of our lives,” his son said. “Life has a greater meaning.”

Mr. Colmar, 88, of Glenview died of congestive heart failure Friday, Aug. 6, in the Hospice of North Shore in Skokie.

Mr. Colmar grew up in Wheeling, W.Va. He came to Chicago on a journalism scholarship to Northwestern University, but became an attorney instead. He received his law degree in 1940.

He suspended his budding law career after the start of World War II to work for Combustion Engineering Co. in Chicago, managing the factories that produced weapons and materials for the war.

Mr. Colmar’s first marriage in the early 1940s ended in divorce. He had two children. He remarried in 1950 to Christine Counadis and had four children.

In 1953 he started a law practice, serving as general counsel and member of the board of directors for more than a dozen local businesses, handling numerous tasks such as labor relations, and financial and corporate development.

When Gibran Baccash started working at a troubled Lincolnwood company in the 1960s, Mr. Colmar, the general counsel, helped Baccash turn it around.

“He was congenial. He was pleasant. He was smart as the devil,” Baccash said. “I was the guy running the thing. I needed help, and that’s where I turned and he delivered.”

Mr. Colmar also was an active Republican throughout his life, and supported the arts and medical research.

He retired in 1995 and lived part time in Florida, basking in the good weather and enjoying golf and bridge with his wife. He dabbled in real estate, traveled extensively and devoted himself to his grandchildren.

Mr. Colmar also returned to his first love–writing. At age 79, he spent six months writing a professionally produced autobiography, titled “Little Me,” and published 500 hardcover and paperback editions of the 126-page book, which included photographs, to distribute to family, friends and colleagues.

He tapped out nearly 100 fiery letters to newspaper editors in Chicago and Palm Beach, and saw nearly two dozen published on topics from terrorism to the Electoral College.

“He was the kind of guy who was incapable of spending his time doing nothing,” his son said.

Other survivors include his wife, Christine; two more sons, John Jr. and Steven; a daughter, Joan; 12 grandchildren; and seven great-grandchildren.

A memorial service will be held at 1 p.m. Sunday in Lutheran Church of the Ascension, 460 Sunset Ridge Rd., Northfield.