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As head of one of Chicago’s oldest real estate and financial firms, Douglas Kramer worked to keep his grandfather’s business growing by expanding its reach into commercial property.

His family’s firm, Draper and Kramer Inc., founded in 1893, has a long history in the city. Mr. Kramer’s father, Ferdinand, helped launch the Metropolitan Planning Council and helped build affordable housing on the South Side and an early urban renewal project in the South Loop.

Mr. Kramer balanced his interests in commercial development with taking on civic roles of his own, including serving as head of the Chicago Crime Commission from 2001 to 2005 and vice chairman ever since.

Mr. Kramer’s specialty was making friends and doing deals, family said, which may be why the Winnetka resident started his workday for at least three decades by presiding over a table at Lou Mitchell’s, the noted diner on the Near West Side.

The eclectic cast that started its day with Mr. Kramer, each taking a turn to pick up the check, were among the friends and family who mourned his death on Tuesday, Dec. 28. Mr. Kramer, 74, who had been battling cancer for decades, died of complications from the disease at Northwestern Memorial Hospital, his family said.

“One of the things that sets Doug apart is how easily he could connect with people,” said Forrest Bailey, Mr. Kramer’s nephew and the firm’s president. “He was avuncular in the best sense of the word.

“And he seemed bulletproof. It’s just sort of hard to conceptualize (his death) because he’d fought the good fight for such a long time — and won.”

Mary Lynn Kramer, Mr. Kramer’s wife of 32 years, met him while working as a senior project designer for Skidmore, Owings & Merrill, which was designing one of Mr. Kramer’s biggest projects, the massive office tower at 33 W. Monroe St. that has housed the architectural firm and the accounting firm Arthur Andersen.

It wasn’t exactly love at first sight.

“I thought he was crazy because he was constantly making all these crazy jokes,” she said. “I said, ‘Who is this guy?'”

But something sparked.

“He was the man who never met a stranger,” she said. “I liked him because he liked people. He was just a great guy.”

After being married in 1978, they took a honeymoon trip around the world. They had a daughter, Kara. Mr. Kramer has three children from a previous marriage, Kathryn Walley, Valerie Kramer and Michele Kramer.

His family also said he loved to golf and fish.

Mr. Kramer also is survived by a sister, Barbara Bailey; a brother, Anthony; and five grandchildren.

Services are pending.

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