Aside from Tronc, there appears to be just one other party trying to buy the Chicago Sun-Times and Chicago Reader from Wrapports Holding.

Edwin Eisendrath III, 59, whose Chicago connections run deep, could end up keeping the struggling tabloid out of the hands of Tronc, the parent company of Chicago Tribune and this magazine. Partnering with the Chicago Federation of Labor, which represents more than 300 unions in Cook County, Eisendrath claims to have raised $15 million from 10 to 15 investors, whose names he won’t reveal.

His motives seem laudable. He says he wants to keep his hometown from becoming a one-newspaper city and to give “the 99 percent,” working Chicagoans, a voice.

Eisendrath has faded from view in recent years; he was once alderman of the 43^rd Ward encompassing Lincoln Park (currently represented by Michele Smith, though the borders have changed), and he was also in the public eye as a failed candidate for both Congress and Illinois governor. Since leaving public life, he moved among business-related jobs and is currently managing partner of StrateSphere, which the Tribune describes as “an Ohio-based business development company.” Should his bid win approval from the Justice Department and the seller, Eisendrath could return to the city’s tempestuous political scene.

In an email yesterday, Eisendrath declined my request to interview him, writing, "I am really tied up while we work on this project … I'm not presently available." I looked closely at his extended family 17 years ago while researching a profile of his mother, Susan, and his stepfather, Lewis Manilow. Here’s some of what I learned.

His boyhood was spent in a grand house on Hawthorne Street in East Lake View. Like his father, Edwin Eisendrath Jr., and his mother, then Susan Rosenberg, he went to Francis Parker School. Harvard followed.

Susan came from a powerful West Side political family, and Edwin Jr. was an attorney. They divorced in 1970 and Susan married Manilow, whom she knew as a fellow Parker parent, in 1973. (Manilow’s father, Nathan, made a fortune in developing the early shopping centers at Old Orchard and Oakbrook.)

The couple was known for the mounds of money they directed to Democrats. They were early backers of Jimmy Carter and Bill Clinton; Lew told me it was he who persuaded Clinton to run for president, and the two helped him finance his run. They were intimate buddies with Al and Tipper Gore. In the summer of 2000, when I interviewed them at their 10,000-square-foot Lincoln Park house on Howe Street built across four city lots, they seemed to me among the biggest political players in the city.

So Edwin III had plenty of financial support when, in 1987, not yet 30 years old, he decided to run for alderman.

During the campaign, he was portrayed as an entitled rich boy whose parents were intent on buying him a City Council seat. His opponent was Robert Perkins, a young lawyer and former aide to Abner Mikva. Pundits dubbed the race “The Battle of the Blue Bloods”—two fancily educated bankers’ sons duking it out. It was then the most expensive ward campaign in Chicago history. Mayor Harold Washington came out in support of Perkins. Marty Oberman, the retiring alderman, also supported Perkins, as did former Mayor Jane Byrne.

But Eisendrath, then 29, had some savvy players in his corner, including his mother and stepfather’s close friend, former 43rd Ward alderman Bill Singer. Eisendrath won, but he was never able to shed the “boy alderman” label. The late Sun-Times political editor Steve Neal took to calling him “Little Lord Eddie.”

Political strategist Don Rose told me at the time that Eisendrath reminded him of George W. Bush. He “had a path cleared for him by family, friends, and money … the kind of person who wants these offices so he can be something, rather than wants the office so he can do something. [He] goes into office without a concept of mission.”

Rose looked like he had a point when, still a freshman alderman in 1989, age 31, Eisendrath announced that he was running in the 1990 Democratic primary against the aged but beloved 9th District congressman Sidney Yates. Eisendrath got clobbered in the polls and in the press—unfairly because Yates, then 80, had been in the job too long. Eisendrath was the first Democrat to challenge Yates in his 40-year congressional career.

The Sun-Times’s Lynn Sweet told me that Eisendrath “was right to make the fight, but he just needed to be smarter. He should have anticipated how beloved Sid Yates was.” (Eisendrath’s humiliating defeat was similar to the one suffered by state senator Barack Obama when he ran and lost big against incumbent congressman Bobby Rush.) Eisendrath went on to win a second term as alderman, but, by 1993, he was jumping to the next opportunity.

He exited the City Council that year for a job as regional director of the Department of Housing and Urban Development. The position was obviously compliments of Bill Clinton: While his parents were big donors, Eisendrath also worked hard for Clinton, particularly in the Illinois primary. Bill Singer told me at the time that Eisendrath “attended every meeting.”

According to Susan, “He hated the public housing situation in Chicago and thought this was a job that would allow him to help. We didn’t say, ‘Okay, Edwin, do you want a job in this administration?’ He said, ‘This is something really fascinating. How do I go about this?’” They relayed the message back to their friends in the Clinton White House. Or, as Bill Singer explained, “You bring yourself to the attention of the appropriate people… Edwin had paid his dues, that’s how it works.”

People who knew Eisendrath told me that his main motive for public service was to help the less privileged. As an alderman he wanted to fix education—he had worked as a public school teacher in Wicker Park, and, before that, in Appalachia. When he left the City Council to take a job at HUD, his motive, friends said, was to help solve the awful problems of public housing, particularly at Cabrini Green.

He stayed through Clinton’s first term, announcing his departure in November 1997. By then married—to Jennifer Schulze, a former news director at WGN-TV—with three children, he said, “I need to make a living.”

Eisendrath had one more race in him: He mounted a late challenge to then Governor Rod Blagojevich in the March 2006 primary. He showed more courage and prescience than other Democratic pols, charging Blago with all manner of ethical lapses and downright corruption. "It took our party nearly 30 years to win the governorship," he said. "In less than four, the Blagojevich administration has left a perception of ethical lapses to put all that we've worked for at risk."

One more note on Eisendrath’s family tree that may seem auspicious to some observers: His grandmother was Lake View resident Louise Sulzberger Eisendrath. Yes, as in the New York Times Sulzbergers.