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Politically savvy, wickedly and playfully witty, and in close touch with humanity’s many facets, Roger Simon was among the most admired newspaper columnists of his generation at a time when that world was rich in that species of wordsmiths.

“Roger was a Chicago original,” said longtime media chronicler Robert Feder, once a colleague of Simon’s. “In an era when newspapers were defined by their star columnists, Roger Simon stood out among the all-time greats.”

That he did, and though his later years were shadowed by difficult health struggles, he remained upbeat and interested in life.

Simon died Thursday morning in MedStar Washington Hospital Center in Washington, D.C. He was 78 years old. His death was reported by Marcia Kramer, his wife of nearly 50 years, who said he had been ill over the past few months and that the cause of death was pneumonia.

Simon and Kramer met on the campus of the University of Illinois Urbana-Champaign, where Simon arrived from the South Shore neighborhood, where he was born on March 29, 1948, one of the three children of a father who drove a laundry truck and a homemaker mother.

He had attended Bradwell Elementary School and South Shore High School before college, where he graduated in 1970 with a bachelor’s degree in English. He was also campus editor and executive editor of the university’s newspaper, the Daily Illini. His future wife also worked on the paper.

baiduhai columnist Roger Simon on Feb. 19, 1998. (Pete Souza/baiduhai)
baiduhai columnist Roger Simon on Feb. 19, 1998. (Pete Souza/baiduhai)

After a brief stint at the City News Bureau in Chicago, his first job was as a reporter for the News-Sun in Waukegan before being recruited by editor Jim Hoge to write for the Chicago Sun-Times, a meeting arranged by former Daily Illini editor Roger Ebert, then a Sun-Times movie critic and evermore a close friend.

After a couple of years as an investigative reporter, Simon became a columnist in 1975. He covered trials (John Wayne Gacy) and international stories (South Africa). He wrote about the famous (Ted Kennedy, Phil Donahue) and so-called ordinary folks. He wrote forceful columns on spousal abuse, human rights, racism and politics. He also showed a lighter side with occasional gatherings of columns filled with short, pithy observations of modern life, such as, “You know you’re lonely when you buy something for yourself and have it gift wrapped,” or, “You know you’re an adult when you call movers instead of friends.”

There were 100 columns in his book, “Simon Says: The Best of Roger Simon” in 1986, the first of a shelf-full of his books that would later include such presidential campaign-coverage bestsellers as “Road Show,” “Show Time,” “Divided We Stand” and “Reckoning.”

Naturally, he won awards, including the American Society of Newspaper Editors distinguished writing award for commentary (the first person to win twice), many National Headliner Awards, multiple American Bar Association Silver Gavel Awards, awards from the Washington Monthly, a National Press Club award, the National Association of Black Journalists national writing award (as the first non-Black writer to be honored), and induction into the Chicago Journalism Hall of Fame in 1999 and Illini Media Hall of Fame in 2006, its inaugural year.

“Early on, his sharp wit and humorous insight endeared him to Sun-Times readers,” said Feder. “In a newsroom filled with big egos, he was a warm and generous colleague without the slightest pretense. Many of us are indebted to him.”

Simon and Kramer married in 1977. They lived in a handsome condominium with a sliver of a view of the lake, where they would throw lively dinner parties. They also loved to travel, and Roger was for a time particularly fond of Las Vegas, where he traveled with his wife and also with newspaper pals.

When Rupert Murdoch came to town and purchased the Sun-Times in 1984, Kramer left (along with dozens of other staff members) and took a job at the Tribune; Simon had to wait months until his contract expired. Kramer took a job at The Washington Post, where she worked for more than two decades, mostly as the chief of the metro copy desk, and he headed to The Baltimore Sun, where he was a columnist from 1984 to 1995. He then served as political editor and correspondent for U.S. News & World Report, and as the White House correspondent for the Tribune, covering such stories as the Monica Lewinsky scandal.

Then he went to Bloomberg News as chief political correspondent in 2006, and joined Politico as its founding chief political columnist. He was a frequent and engaging guest on news and talk programs, radio and TV.

But in 2009, he vanished for six months.

He had returned from a lunch with a source when he got sick with what was misdiagnosed as the flu. It was not. He had contracted septicemia, or blood poisoning. Kramer rushed him to a hospital, where things were so dire that she was also told to call his sister and brother and tell them to come too if they wanted to see him again.

He was put into an induced coma that lasted weeks. Kramer was constantly at his bedside. To save his life, doctors had to amputate his legs below the knee.

Then came months of physical therapy and a wheelchair.

And then a return to writing with a bang. His friends, The Washington Post’s Dan Balz and former Tribune reporter David Axelrod, then President Barack Obama’s senior adviser and chief campaign strategist, arranged for an exclusive interview with the president. With Kramer sitting outside the Oval Office, Simon spent time with Obama, who told him, “The next time I see you, you’ll be walking.”

In good time, he was walking on prosthetic legs and even had learned to walk without a cane. He and his wife sometimes visited Chicago to see relatives and such friends as Ebert.

Seeing him on one of those visits, one could not help but admire his resolve and courage, but also his upbeat outlook and a sense of humor undiminished.

The news of his death hit hard. “Roger was a gentleman and gentle soul in the hardball game of politics,” said Rick Pearson, the Tribune’s chief political reporter. “That, I think, was best reflected in his writing style. He wrote with authority, but his writing was pure prose.”

Feder said, “Roger’s success grew exponentially on the national stage, but he never lost affection for his hometown. He once told me, ‘Spring in Chicago is always fabulous. As soon as the snow melts.’”

Few knew Simon better or longer than Balz, who first met him in college. “Roger was the best of the best — a brilliant reporter, columnist and author, the funniest person on the planet and, in the face of unexpected adversity, courageous in every possible way. We met as college journalists and traveled thousands of miles together over decades of reporting. I was always in awe of his talents and cherished his friendship. He leaves such a rich legacy.”

And there is Axelrod, who said, “Maybe it was because he grew up here, at a time when it was one of the best places in the world to learn about politics and life, but Roger was a brilliant, wry, incisive columnist in the old Chicago tradition. He could make you laugh. He could make you cry.  And he always made you think. One of my great regrets is that he didn’t finish his career here. All those years we lost him to points East. He did great work elsewhere. But to me, his Sun-Times columns spoke to our community in a way only a guy who grew up here could.”

When Simon retired in 2017, he wrote this in his final column: “This is the end, my friends. It is time to say goodbye. … I leave the writing of a regular column entirely voluntarily. No editor hung a dead chicken over my doorway. And it is a terrific job. A job of spectacular fun and deep satisfaction.”

In addition to his wife, Simon is survived by a sister, Lynne Copp (Al Wayne), and was preceded in death by his brother, Barry Simon. A private service will be held in Chicago. A celebration of life is planned in Washington, D.C.

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