John Eisendrath's cover story on the radical community leader Slim Coleman, from the December 2, 1983, edition of the Reader.

When the name Edwin Eisendrath surfaced a few weeks ago as someone putting together a team to buy the Chicago Sun-Times and the Chicago Reader, I said it was good news. The former 43rd Ward alderman’s younger brother John had been a Reader staff writer in the early 80s and most likely he retained some affection for the paper. Perhaps that affection might save the publication.

News in May that the Sun-Times and Reader might be sold to Tronc had put the fear of God in the Reader staff. Michael Ferro, head of Tronc, had controlled the two papers once before, and when he went away, lured by the giddier empire-building possibilities of Tribune Publishing (a last century corporate moniker Ferro promptly discarded when he took over), everyone he left behind did a happy dance. His Michael Myers-like reappearance wasn’t the only reason the Reader staff winced. Public statements on the absorption of the Sun-Times into Tronc as a separately run sister of the Tribune made no mention of the Reader at all. Were we chopped liver—or less? Would Ferro, who’d shown little to no interest in the Reader the first time he controlled it, kill off the paper and butcher it for parts? (Word earlier this month of Tronc’s plan to close the alternative weekly Baltimore City Paper didn’t bode well for the Reader were it to come under the company’s ownership.)  

Surely Ed and John Eisendrath represented a better bet for survival.

Now that I’ve talked to both of them, I think they do. “I don’t think there are any guarantees for any of us,” says Edwin, now CEO of the new ST Acquisitions Holdings LLC, when asked about the Reader‘s fate. But he knows this paper well and values it. “Ben and I have known each other for ages and ages,” he says, speaking of longtime political writer Ben Joravsky. “It’s been part of my life.”

Minutes before Edwin and I spoke by phone I’d been reading “Why is this man running?,” the story Joravsky wrote about him in 1990 when he was trying to unseat congressman Sidney Yates. (He didn’t.) “It was a nice piece,” I say. “It went on forever.”

Says Edwin, “John didn’t like that one either.”

In 1987 Edwin, a school teacher still in his 20s, decided to run for alderman of the 43rd Ward. John, younger by a year and a half, was in Washington, D.C., by then, writing about politics for the Washington Journal after breaking into journalism with the Reader (his day job) and the old City News Bureau (his night job). John came home to help his brother campaign.

“When I came to Chicago to help this guy who I knew didn’t have a selfish bone in his body, who had worked as a public school teacher and wanted to help people who lived in the city,” John says, “all I saw were reporters cynically suggesting that he had no real reason to run, he was a spoiled rich kid, he was a snot-nosed Harvard rich kid who was trying to buy his way into office. They didn’t spend two seconds trying to understand him.”

John’s memory didn’t fail him here. Chicago magazine’s Carol Felsenthal recently recalled that Edwin “was portrayed as an entitled rich boy whose parents were intent on buying him a City Council seat” and that the Sun-Times‘s then political editor took to calling him “Little Lord Eddie.”

The brothers’ mother, Susan, came from a politically important west-side family and their stepfather, Lewis Manilow, was a rich developer, arts patron, and Democratic Party activist.

John continues, “I thought, ‘Is that what I do? Is that how I behave when I’m covering people?’ And I thought, ‘Yeah, I’m no different. I hate this. I can’t do this for a living.’ And I quit. And now that I think about it, I was way angrier than [Edwin] was. He remained empathetic. He remained understanding—to a degree I am completely incapable of.”

“It’s harder on the family,” Edwin allows. “It’s ancient history.”

When Edwin ran against Yates—nobody ran against Yates, who’d been in Congress since Truman was president—he was again judged too eager and presumptuous. But it was Edwin’s last race—years after leaving the City Council and running the regional office of the Department of Housing and Urban Development—that John can’t think about without boiling over. In 2006 Edwin challenged Governor Rod Blagojevich in the Democratic primary. “At the time, Rod Blagojevich was already under investigation by [U.S. attorney] Pat Fitzgerald—everybody knew it,” John says. “Everybody knew Rod Blagojevich was a corrupt, crooked politician. One person in the Democratic Party stood up and said the state of Illinois should have a better person representing them. And my brother was rewarded by having everyone in the elected delegation of Democrats in the city and state who knew Rod Blagojevich was a a crook endorse Rod Blagojevich. They held their nose and endorsed him over a smart, hard-working, caring person. And I wouldn’t give any of those people the time of day if I ever saw them again.

“But my brother rose above it. When they went low, he went high.”

(Here, the Beachwood Reporter offers a more dispassionate look back at that race.)

John tells me Edwin’s handling by the press in ’87 made him reappraise all of his own journalism. It didn’t measure up. He remembers a Reader story he wrote on someone in the Harold Washington administration that “referenced something he did as being as bad as the trade that brought Lou Brock to the Cardinals. It had that disparaging, condescending, oh yeah I’m summing you up [attitude]. I looked back on it and I thought, ‘How was it OK for you to summarize someone’s work so dismissively?’ That was the worst example.”

Then there was the cover story on Al Gore he wrote for Washington Monthly. “I hung out with him and it was mostly positive, but it was a—you know—I’m sure what I was writing seemed a lot more confident that I knew who that person was than I really did. It was as much bravado as it was true knowledge.”

Not that John was the first reporter to look bleakly into the mirror. And not that he lost all respect for journalism. He knew there were reporters older, more mature, and a lot more empathetic than he’d decided he was. But, he says carefully, picking his way through the thought, “I couldn’t see myself doing to other people what I saw other journalists doing to Edwin. So I said let me see if there’s another way of making a living as a writer.”

There was. He went to LA and became a writer and producer of hit TV shows. The shows he’s been heavily involved with include Beverly Hills, 90210, Alias, and, currently, The Blacklist. And John understands why alderman Ed Vrdolyak appealed to City Hall reporters back in the day a lot more than upright Edwin Eisendrath did; it’s why he relishes writing lines for The Blacklist‘s smirking Raymond Reddington, the master criminal who knows absolutely everybody worth garroting. Bad guys make better company. “He gets to do what you can only fantasize about,” John says. “Sure, I get it, I totally get it.” Then again, “Red” Reddington isn’t scheming against John’s big brother.

“We are close now, we have been close always,” Edwin says. “We talk to each other every day. I would do anything for him, I think he would do anything for me.”

And now?

“He jokingly said he’d like to write the bad-advice column.”

John says he’s so far out of the Chicago media loop that he wasn’t aware the Sun-Times and Reader were commonly owned by a group of investors called Wrapports until a few days before his brother (allied with the Chicago Federation of Labor) took over both of them. But he’s at Edwin’s service. He put a few dollars in the pot so he’s also one of the new owners; and although he doubts his brother will ask more of him than that, he didn’t sound unwilling to be useful. “I’m closer to the end of my career than the beginning, and I’d like to go back to some kind of nonfiction,” John says. “You know, I loved being a reporter. And when I size it up to being a screenwriter, I think I’m a better reporter.

“I’m incredibly fond of the Reader,” John goes on, “but if you’re asking if my history with the Reader will have any effect, I have no idea. But does my brother understand his little brother got his start as a writer writing for the Reader—sure he does.”