Two years ago Dawn Reiss left a good reporting job at a Florida newspaper to take on Chicago. She had no work waiting for her here and knew almost no one. Unless some golden opportunity fell into her lap, she’d have to chase her dream as a freelancer.

So Reiss printed up 150 business cards and bought a ticket to the Lisagor Awards dinner, the bash thrown annually by the Chicago Headline Club, the local chapter of the Society of Professional Journalists. “I gave out 100 business cards,” she says, “and I had ten assignments by the end of the night.”

The other day I received an e-mail trying to drum up interest in this year’s dinner, which is April 24 at the Union League Club. “We want to encourage journalists and other interested parties to show their support for the journalism community by attending the awards dinner,” wrote Brian Pitts, a publicist and Headline Club member. “Can you help us create some buzz for the awards and the dinner?”

Was there, to Pitts’s unusual appeal, a ring of desperation? On my blog recently I described how the Tribune Company had recently spent thousands of dollars less than it would have in better times on Washington’s Gridiron Club dinner. It stood to reason that the bankrupt Tribune Company—as wells as the city’s other struggling media outlets—would decide to cut corners at the Lisagors too.

Reservations can be made until April 20, but some media shops have already made their intentions known. The Tribune used to buy two tables; last year it bought one and this year it’s buying one. Last year the Southtown Star bought a table; this year it’s sharing a table with the papers in the Sun-Times Media Group’s Fox Valley Group. Last year Pioneer Press bought a table and won a couple awards; this year there are no Pioneer Press finalists—and there’s no Pioneer Press table either.

When times were good, the club’s executive director, Kathy Catrambone, told me, about three checks out of four reserving places at the dinner were corporate checks. This year, she estimates, three out of four are personal checks.

Looking for a forecast, I called the president of the Headline Club—none other than Dawn Reiss. At the suggestion of Meg Tebo, a former Headline Club president and someone Reiss did know in Chicago, Reiss joined the board two years ago, and last June she was elected president. Normally there’s a president-elect who takes over. But the president-elect decided to go to law school and another vice president got a better job out of town. So a power vacuum existed and Reiss was ready to fill it.

“Actually, it’s too soon to tell,” she said, when I asked her if this year’s dinner will fill the room. “We’ll see what happens. I think people want to network. Ben Myers was laid off at the Chicago Journal but he bought a ticket to network. This is the one chance they’ll get.”

The Headline Club has been around since 1921 and its purposes are traditionally lofty. But these aren’t normal times. “It’s great to have programs to talk about topics like ethics and diversity,” said Reiss, “but there needed to be more hands-on programs. When you’re getting downsized it’s important to talk about things that are not taught in the newsroom—like how to freelance. I’ve been inundated by people who need help. There’s this sense of desperation and this is where the club can step in. We had a program last year on how to transition into different fields—like teaching and PR. People are scared. They’re overworked and tired. Even if people have jobs, they’re not getting trained. Newsrooms used to have the funds and people to train their people. Now they don’t.”

When Reiss took over as president she started a monthly burger night—inviting veterans to drop by the Billy Goat to kick around ideas for an hour or two with any other journalists who wandered in. I was Reiss’s guest a month ago. There are only two topics anymore—the death of media and the transformation of media. Somebody said weekly community newspapers seemed to be holding their own, and I replied that I’d just spent the afternoon working up a blog post on Wednesday Journal Inc.’s decision to shut down three of its weeklies. One guy in the small crowd wryly complimented me on my reporting skills. He hadn’t heard yet what Wednesday Journal was doing, and he was one of its editors. He left early.

The Headline Club used to throw two dinners a year—one in the spring to hand out Lisagors and another in the fall to present its lifetime achievement award. The latter dinner wasn’t held in 2008 and now the two events have been combined. The club’s giving two lifetime awards on April 24—to political reporters Fran Spielman of the Sun-Times and Andy Shaw, recently retired from WLS TV. (Spielman’s award might explain why the Sun-Times has bought four tables.)

But if austerity has to be observed on the one hand, Reiss wants plenty of razzamatazz on the other. “We’ve got five students who’ll wear trench coats and fedoras and they’ll go around with clipboards doing a silent auction,” she says. “We’ll have two emcees for the first time—Felicia Middlebrooks of WBBM and Phil Ponce of WTTW.” And the keynote address will somehow, some way, be delivered jointly by Jane Hirt, late of RedEye, now managing editor of the Tribune, and Don Hayner, editor of the Sun-Times. “Which,” says Reiss, “is like East Berlin and West Berlin, when you come to think of it.”

Reiss has appointed an official Headline Club twitterer, and she intends to have a video of the dinner posted on YouTube before the night is over. She says, “We’re in a multimedia world, so why don’t we embrace that?”

I reached Ben Myers, the out-of-work editor Reiss said was coming to the dinner to network. His last job was editor of Skyline—ironically enough, a Wednesday Journal weekly the company decided to keep. Myers wasn’t so lucky. “Change is afoot,” announced Skyline on March 11 in a message to readers from publisher Dan Haley. “Local news is staying, but it will come to you from a consolidated staff of our reporters. The position of Skyline editor, which Ben Myers has filled with such energy in the last year, is one of seven jobs we have cut.”

Myers, a finalist for two Lisagors—for in-depth reporting and editorial writing in the community newspaper category—thought he’d be attending the dinner on his own dime until Haley called him this week to say the company would cover the ticket. “Frankly,” Myers told me before he knew that, “I don’t know if I’d be able to shell out 80 bucks for a ticket if I wasn’t a finalist. I wanted to go see if I won.”

But, he went on, “it’s a wonderful chance to connect with people, particularly where I’m in a situation now where it’s pretty vital for me to do so. I don’t know how realistic it is to find stable work right now. I hope to cobble together a living over the next couple of years until things open up again. I’ve got to get on this networking game. I see the next couple of years as a big sort of bridge.”

To nowhere?

“No. It’s a bridge to somewhere,” Myers replied. “I just don’t know where exactly.”

StreetWise on the Curb?

Among the more unstable inclinations of the human heart is its desire to give away money to worthy causes. Offered a pretty good reason to stop giving, many of us gladly take it. StreetWise was forever tarnished as a favored cause of mine in 2001, when, as I began a column then, “The editor of StreetWise and other staffers went into open rebellion” against the executive director. The rebels, who had my sympathy, as they championed the editorial quality of the newspaper, wound up leaving StreetWise, and thereafter I’ve felt Chicago’s street paper isn’t what it should be and guarded my wallet accordingly.

Now StreetWise is in trouble. “The current economic slowdown has hit this 16-year-old nonprofit in the pocketbook like a ton of bricks,” said a Monday release from the paper’s City Council champion, Manny Flores. “The iconic Chicago organization now finds itself at risk of being out on the street.”

By coincidence, Flores made his announcement the same day the New York Times reported that “newspapers produced and sold by homeless people in dozens of American cities are flourishing even as the deepening recession endangers conventional newspapers.” The economy, said the Times, “has hardly been a windfall,” but it has “heightened interest in their offbeat coverage and driven new vendors to their doors.”

The article focused on street papers in Seattle and Portland. Suzanne Hanney, editor of StreetWise, told me she knew those papers “and they are very well run and they are very newsworthy. I don’t know if Chicago’s harder to please, harder to impress, or more conservative. It may be that everybody’s crunched in Chicago. When you have more to give, you do.”

I’m not sure the editorial content ever quite recovered from 2001, but Hanney wasn’t the editor then, Bruce Crane wasn’t the executive director, and they’re right—it’s ancient history. The problem, says Crane, is grants, or the lack thereof: “We used to depend on $120,000 in foundation support,” he said, but “this year’s budget has about $60,000 we’re hoping for, and we figure that may not materialize.”

StreetWise has never received government funding, Crane says, but other not-for-profits have, and as it dried up they turned to the same foundations StreetWise has relied on—foundations with now battered endowments. “We’d love to get funding through the stimulus package,” Crane says. “We certainly feel we’re the right kind of agency to get that kind of help.”

Who do you have in Washington? I ask. “[Congressman] Danny Davis has been a wonderful friend for many years,” Crane says.

The economy has brought to StreetWise‘s door many more jobless people looking to become vendors. “It used to be we’d get eight to ten new vendors a week,” Crane says. “Now it’s around 20.”

Crane says StreetWise is a couple months from the brink, and it raised the alarm now because “it would be irresponsible if we waited until it was too late.” He wanted the public to hear two things. “One. Look at your vendor and realize it’s his livelihood—he and his family depend on this. Two. Consider sending some money to StreetWise. Ten bucks goes a long way.”

Something else he said made me wince. The public, he says, has “the misperception that if they don’t take the magazine they’re helping the vendor. They’re hurting him. It helps the vendor with his dignity by taking the magazine. And we get the incremental circulation—which is what drives ad revenues.”v

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