Roy Wiley dies at 87; former Sun-Times reporter, editor went on to career in business communications

Mr. Wiley started as a copy clerk in 1952, working from midnight to 8 a.m., and attending classes at Northwestern University during the day.

SHARE Roy Wiley dies at 87; former Sun-Times reporter, editor went on to career in business communications
Roy Wiley with his wife, Bobbie Huskey, in 2014.

Roy Wiley with his wife, Bobbie Huskey, in 2014.

Sun-Times files

Roy Wiley got his start at the Chicago Sun-Times as a young college student.

Mr. Wiley was hired as a copy clerk in 1952. He worked from midnight to 8 a.m., then went to school during the day. And in the newsroom, he did anything and everything.

And that’s when, his wife Bobbie Huskey recalled, he finally got his chance.

A story needed covering, but no reporters were available. An editor looked at Mr. Wiley.

“You want to be a reporter, right?” he asked.

“Yes, sir,” Mr. Wiley answered.

That’s how he got his first assignment.

Soon, Huskey said, he was offered a full-time general assignment reporter job — but it would mean putting off college.

It wasn’t an easy decision, Huskey said, but Mr. Wiley wanted to be a reporter. “Then take the job,” a mentor told him.

He did. And he remained in the media business the rest of his career.

Roy Wiley, on the job at the Chicago Sun-Times in 1960.

Roy Wiley, on the job at the Chicago Sun-Times in 1960.

Sun-Times file photo

Mr. Wiley, of Chicago, died April 4 at Northwestern Memorial Hospital while recovering from hip surgery. He was 87.

Mr. Wiley spent about 16 years at the Sun-Times, where his jobs included automotive editor, marketing and stock market columnist, and assistant financial editor.

He also served as executive editor of Automobile Fleet magazine, then editor and publisher of American Savings & Loan Weekly.

“This man had newspapers in his blood,” said Huskey, who married Mr. Wiley in 1989.

Huskey said he caught the bug at Onarga Military School in Elmwood Park, editing the newspaper and yearbook.

Before that, he delivered newspapers to houses in his North Side neighborhood, where he was born and grew up.

Roy Wiley, second from left, in a meeting at the Chicago Sun-Times around 1955.

Roy Wiley (second from left) in a meeting at the Chicago Sun-Times around 1955.


Mr. Wiley left the Sun-Times in 1968 to become senior vice president at the Financial Relations Board. After that, he served in a string of public relations and communications positions at Weber Cohn & Riley, Ogilvy & Mather, Hill & Knowlton, and Navistar International Corp.

Mr. Wiley never stopped working, said Daniel Ustian, who knew Mr. Wiley for more than 20 years and worked closely with him as CEO of Navistar.

That’s because Mr. Wiley loved his work, Huskey said.

“Do you know the best thing about Friday?” Mr. Wiley would say. “It’s only two days before Monday.”

Wiley liked being available night and day for any emergencies. That included on Dec. 31, 1999, when Wiley took a call at 11:59 p.m. to make sure Navistar’s computers smoothly transitioned to the year 2000.

“We were at the Chicago Symphony, on the floor dancing,” Huskey said. “He says I’m sorry, I have to go.” Around 10 minutes later, “he hung up and came back on the dance floor.”

To get to Navistar from his Lake View home, Mr. Wiley left at 4:30 a.m. to take two buses to Warrenville — in his early 70s.

Roy Wiley at the Outboard Marine Corporation, which he handled public relations for, around 1998.

Roy Wiley in 1998 at the Outboard Marine Corp., where he handled public relations.


“What I found amazing about him [was] he knew everybody,” Ustian said. “He knew people half his age, like they were his best friends.”

People were drawn to him by his positivity, Ustian said. When faced with challenges, Mr. Wiley would reassure him everything would work out. “Today was a bad day, tomorrow will be a great day,” he’d say.

Ustian recalled Mr. Wiley sometimes would break the tension in tough meetings by declaring: “OK, it’s time for some ice cream.”

Jim Sloan, who worked with Mr. Wiley for around 15 years at Hill & Knowlton and Navistar, said he knew how to handle tough communication challenges and was committed to his clients.

He also had a fun-loving side. He said Mr. Wiley would keep a bottle of Tabasco sauce on his desk and bet new employees he could drink from the bottle.

If they doubted him, “he would pick it up and take a swig and not bat an eye,” Sloan said.

Huskey met her future husband in 1983, at Riccardo’s restaurant in Chicago. He caught her eye and ordered her a drink. They married six years later.

She loved his cool demeanor, his sense of humor and his sense of style. He wanted to stay fit and independent, even in his later years.

“He liked being dapper,” Huskey said.

Roy Wiley in a tux at a fundraiser at the Fourth Presbyterian Church in Chicago in 2010.

Roy Wiley,at the Fourth Presbyterian Church in Chicago, for a fundraiser in 2010.


Mr. Wiley always wore suspenders; even “a casual day,” Ustian recalled, meant Mr. Wiley would have “suspenders on, with a tie.”

Mr. Wiley loved Chicago, Huskey said — the architecture, the art, the culture — and the Cubs.

“I think about his life and what he has contributed to Chicago,” Huskey said, “and all I can think is that Chicago has lost a piece of its history with his passing.”

Besides Huskey, survivors include two children, Roy Wiley and Cindy Wiley Hindel; nine grandchildren; and three great-grandchildren. A memorial service will be held June 1 at Fourth Presbyterian Church in Chicago.

Roy Wiley, driving a 1929 DeSoto roadster, pays his toll at the 87th Street exit off the Skyway.

One of Roy Wiley’s assignments for the Sun-Times involved driving a 1929 DeSoto from Detroit to Chicago. Here, he pays his toll at the 87th Street exit off the Skyway.

Sun-Times file photo

The Latest
Daeshawn Hill was arrested for fatally shooting Donte T. Shorter on April 30 in the 100 block of West 113th Street in Roseland, Chicago police said.
We rejected Donald Trump’s xenophobia in 2016 and 2020, and Chicago must reject it now as the presidential election and Democratic National Convention approach in 2024, state Sen. Robert Peters writes.
Feeling stuck in a comfort-over-fashion limbo? A stylish Chicago young woman talks about what motivates her to dress nice against chilly odds.
Reader doesn’t want a roommate but worries about the safety and living conditions of friend living in a car.