It would be too harsh to call Don Terry a cautionary tale. He’s closer to a warning—and a gentle reminder—that in the 21^st Century, the business of journalism, the careers of newspapermen, are all too fleeting and fickle.

A talented writer and reporter, Terry crafted great stories on topics ranging from the genocide in Rwanda, to the life of an exonerated death row inmate, to Obama advisor Valerie Jarrett. He got into the profession with the noblest of purposes: “To be a freedom fighter. To comfort the afflicted and afflict the comfortable, and I still try to do that.” Despite his prowess and body of work, in February 2009, the Chicago Tribune laid him off, a casualty of the decline of the American newspaper.

Now with the Chicago Sun-Times, writing columns nearly one-tenth the size of his features, he has time on his hands. Time to discuss his career, impart some knowledge and ruminate on the future of the business. So at the end of the 20-foot-long table Terry sits, surrounded by students, discussing his brilliant 2006 Chicago Tribune profile of Reverend Jesse Jackson, “God’s frequent flier”. “One of the best long form pieces I’ve ever read in a Chicago newspaper,” says Alan Solomon, himself a longtime writer and the man who invited Terry to speak to this group of aspiring journalists.

Describing his journey with Jackson, Terry endears himself to his audience, with a quiet charm and wit. In his brown tweed jacket and white button-down shirt tucked into his jeans, the 52-year-old with the salt-and-pepper hair looks and behaves more like an affable history professor than the stereotype of a grizzled, bitter newspaperman. After ditching his prepared script, his mood becomes jaunty and self-deprecating. When a one-liner elicits a round of laughs, he boosts himself up in his chair playfully like a meerkat, grinning, extending his neck and jutting his jaw to the side.

The audience’s attention is rapt as Terry recounts following around the peripatetic preacher for the better part of the summer, wanting to see what made his fellow South Sider tick and to explain who Jackson is, beyond the sound bites and characterizations. Terry trailed him from LA to New York, from Atlanta to Venezuela, observing the man, trying to peel back the layers to see what resided in Jackson’s core.

“To get into someone’s head and heart takes a long time,” Terry says. “Especially with someone who’s so used to reporters, cameras, questions and protecting himself around the media.” Unfortunately, time is money. Something the bankrupt Tribune Company lacks at the moment, so the paper can’t make the significant investment needed to write and report stories the caliber of the Jackson piece.

“The Tribune was paying for every hotel, every meal, every airplane flight,” Terry says. “We were all over the place. So that’s really expensive. They’re going to do less of that. It’s not going to disappear, but they’re going to do less of that,” which leaves a seasoned pro like Terry relegated to the sidelines of the industry. He admits the current media landscape, defined by budget cuts and time constraints are “keeping [him] unemployed.”

“Right now I have to cobble together all kinds of stuff to make ends meet. If I wasn’t married to my wife, I’d be living out of my mother’s house right now,” the gallows humorist says with a chuckle.

To a room full of graduate students at the Medill School of Journalism his assessment of the industry is as portentous and depressing as the damp, cloudy skies in full view through the windows spanning the classroom’s eastern wall.

It’s hard to see when the newspaper industry’s growing pains will subside, while it sheds customers and its remaining subscribers age. “One of the great challenges in our business is finding a way to maintain a quality product and also appeal to the next generations who have to support you to exist and it’s been a difficult task,” says Solomon. The baby boomers may be the last American generation to engage with the printed version of the daily paper and Solomon can see the change every day at his doorstep. He’s noticed that in his 11-unit condo building “the seven people who get the Tribune are all in their 50s and above,” he explains. “The audience is changing and it’s dying out”

The generation divide is evident to Terry as he peers around his alma mater’s classroom and sees every student with their computer in front of them.“I went to Medill, class of 1980. You all have laptops, when I came in and they had a selection of IBM typewriters and I thought I had died and gone to heaven. So fancy!” he says to a chorus of laughs.

Perhaps more importantly than changing the way news is reported, Terry says technology has changed the way journalists are compensated, which could make the profession prohibitive. “One reason that we were able to make a living as journalists for as long as we did was because we were paid a living wage,” Terry explains. “I see this internet stuff, they basically want you people to work for free.”

Yet among the aspiring scribes, there’s a feeling that a new order may emerge from this uncertain time and that with the current economy, journalists aren’t the only ones licking their wounds. “There’s tons of laid off bankers right now, what’s the difference?” Kim Wilson says, “It’s maybe cyclical and there may be opportunity with things in flux.”

Terry tells the students it’s in their hands to figure out the future of the profession. The students tell the old master there’s still reason for hope. Still a reason to pursue the profession he loves. Still work to be had.

“I’m an optimist,” remarks Emily Co. “I heard there’s spots open in Baghdad.”