Fourth Ward alderman and Democratic candidate for Cook County board president Toni Preckwinkle
Fourth Ward alderman and Democratic candidate for Cook County board president Toni Preckwinkle Credit: Marc Monaghan

Just about everything good to emerge from the miserable swamp of Chicago politics has some connection to the communities lodged roughly in the area between 43rd and 60th streets on the north and south and from the lake to Cottage Grove. It’s the birthplace of independent antipatronage politics and one of the few racially integrated neighborhoods in town. The area’s divided into two wards, the Fourth and the Fifth, so ambitious activists have twice as many opportunities to rise up the political ranks, and it’s home to the University of Chicago, which over the years has launched so many self-serving urban renewal projects and economic development schemes that the locals have gotten really smart about fighting them off. Dozens of savvy politicos and politicians got their chops fighting the University of Chicago, and many of them even went to school there.

This progressive political tradition starts with New Dealers like Fifth Ward aldermen Paul Douglas and Robert Merriam. Douglas made it all the way to the U.S. Senate, and he might have died there if he hadn’t supported President Johnson’s Vietnam war policy. The lefties in the Democratic Party—Hyde Parkers included—turned against him, voting for Republican Charles Percy in 1966. As a matter of fact, I know some lefties now pushing 90 who still haven’t forgiven Douglas.

Next came the independent crusaders of the 50s, 60s, and 70s, led by Leon Despres and Don Rose. Despres was simply the greatest independent alderman in Chicago history; he died last year at 101. He started fighting for open-housing laws and other civil rights causes almost as soon as he became an alderman in 1955, and he kept up his crusade through the tumultuous 1960s, when southwest-siders were hurling rocks at Martin Luther King. In the 20 years he represented the Fifth Ward in the City Council, Despres stood up to old man Daley on issues of patronage (he scoured the budget looking for ghost payrollers), preservation (he unsuccessfully urged the city to fight harder to save historic buildings from demolition), and open space—during a contentious 1970 council debate over the city’s proposal to construct a school in Washington Park, Despres argued that public parks shouldn’t be turned into construction zones. Daley erupted and called Despres a liar, and the alderman responded by challenging the mayor to a public debate—which Daley ignored, much to the disappointment of Despres.

Former Fifth Ward alderman Leon Despres in 2008
Former Fifth Ward alderman Leon Despres in 2008Credit: Marc Monaghan

For his efforts over the years, the Independent Voters of Illinois-Independent Precinct Organization named its highest award for public service after him. In fact, it’s a shame the IVI-IPO feels obligated to give somebody the award every year, because very few politicians deserve to be mentioned in the same breath as Depres. Last year’s winners should have been the elected officials—aldermen, county commissioners, state legislators, congressmen, and senators—who, like Despres himself, dared to oppose Mayor Daley’s bid to win the 2016 Olympics (which, of course, would have turned several parks into construction zones). Except that there weren’t any.

Longtime Hyde Parker Don Rose, meanwhile, served as press secretary for King when the civil rights leader brought the movement to Chicago in 1965 and 1966, and he also advised independent political candidates. In 1979 Rose orchestrated Jane Byrne’s stunning triumph over Mayor Michael Bilandic and what was left of the first Daley machine. During the campaign, Rose encouraged Byrne to rail against aldermen Eddie Vrdolyak and Ed Burke, calling them an “evil cabal.” Unfortunately, once in office Byrne cut a deal with them, allowing Vrdolyak to remain chairman of the important building and zoning committee and Burke to keep chairing the police committee.

But Rose got his revenge. In 1983 he helped fellow Hyde Parker Harold Washington defeat Byrne. Washington, Chicago’s first and only black mayor, had actually grown up in Bronzeville and got his start in the Third Ward, but he eventually moved to Hyde Park. His fund-raisers and rallies were emceed by music impresario Sid Ordower, whose booming voice gave him the air of a ringside boxing announcer, calling out all “the champions of justice” in attendance.

In 1987 a Rose protege, native New Yorker and U. of C. grad David Axelrod, helped Washington win reelection. Alas, after Washington died, Axelrod went over to the other side, becoming one of Richard M. Daley’s chief strategists and spokesmen. Later, of course, he had a thing or two to do with that Obama fellow getting elected president.

Despres and Rose were allied with many of the city’s greatest civil rights and political leaders, all from Hyde Park or Kenwood, such as Al Raby (an aide to King and Washington), Marshall Patner (one of Despres’ earliest campaign managers), John McDermott (founder of the Chicago Reporter and, coincidentally, the person who gave me my first job), and state senator Richard Newhouse. Newhouse should have been elected mayor in 1975, but former alderman Billy Singer, running as an independent, siphoned off the north lakefront vote, thus allowing old man Daley to win again. Singer went on to become a zoning lawyer. If you can’t beat ’em . . .

Hyde Park also produced hordes of election-rule lawyers and political strategists such as Sam Ackerman, David Cantor, Louis Silverman, Alan Dobry, Lois Dobry—the list goes on and on. They helped launch the careers of Carol Moseley Braun, who in 1992 became the first African-American woman to serve in the U.S. Senate, and Fourth Ward alderman Toni Preckwinkle, who just won the Democratic primary for Cook County Board president.

Of course, not everyone from the area has been a progressive. In the 1960s former Fourth Ward alderman Claude Holman was the anti-independent Boss Daley used to call on to mock and try to intimidate Despres whenever the mayor thought he was getting too uppity with his civil rights legislation. Holman was also a key member of what became known as the “Silent Six”—the half-dozen black aldermen who, in deference to Daley, helped thwart Despres’ civil rights initiatives in the 1960s.

Fifth Ward Democratic committeeman and former city treasurer Marshall Korshak also lived in the neighborhood. In 1969 Korshak rallied city and county workers on behalf of a couple of candidates for delegate to the Illinois Constitutional Convention, prompting Michael Shakman to file his famous lawsuit against the patronage system. Shakman, then living in Hyde Park and contending for one of the convention delegate spots, claimed it was unconstitutional for party bosses like Korshak to compel government workers to campaign for the party’s candidates.

Korshak’s brother, Sidney Korshak, made his own name as a lawyer for the mob. When he died in 1996, the New York Times wrote: “It was a tribute to Sidney Korshak’s success that he was never indicted despite repeated federal and state investigations.”

And then there was Fifth Ward alderman Larry Bloom, who, as Rose puts it, “is our only jailbird.” In 1998 Bloom pleaded guilty to filing false tax returns as part of Operation Silver Shovel, an FBI investigation into bribery at City Hall. Hey, no neighborhood’s perfect.

And speaking of imperfections, Bernie Epton also hailed from Hyde Park. He’s the moderate Republican state rep who ran as the Great White Hope against Washington in the 1983 mayoral election. I interviewed Epton not long before he died in 1987, and he was still bitter about his Hyde Park neighbors, black and white, having deserted him in the election. Epton used to belong to KAM Isaiah Israel, a reform synagogue on Hyde Park Boulevard. But after KAM’s rabbi began bashing President Ronald Reagan in the early 1980s, Epton left the congregation in protest.

Rabbi Arnie Wolf
Rabbi Arnie WolfCredit: Marc Monaghan

The rabbi? Why, he was the great Arnie Wolf. He was my go-to source for information about black-Jewish relations. Whenever I called him he’d tell me that what he had to say was too important to say over the phone, so I’d schlep down to his synagogue and meet him in his book-lined office, where he’d proceed to tell me one great story after another about everything from marching with Dr. King to having James Baldwin (he called him Jimmy) stay at his house. The man must have had a million friends. Rabbi Wolf died in December 2008—too soon for me, but he stuck around long enough to see one of his old friends (and neighbors) get elected president.

President Obama moved to Hyde Park when he got out of Harvard Law School in 1991. It’s where he first sought office, running unopposed for the state senate after he bumped incumbent Alice Palmer from the ballot over nominating-petition irregularities. You might say the president learned fast how to make his way in Chicago politics—I don’t think he learned that stuff in Hawaii.

For better or worse, Obama set the current model for local elected officials: talk a big game about reform but stay out of fights with Mayor Daley. In my humble opinion, we could use a few more outspoken independents like Despres and Newhouse. But the current generation of Hyde Park pols—state senator Kwame Raoul, state rep Will Burns, and Fifth Ward alderman Leslie Hairston—favors the Obama approach. They’ve—oh, how to put this—made their peace with the mayor.

You can’t completely give up on them, though. Harold Washington didn’t make his big break from the machine until 1977, when he was 55 years old. Raoul, Burns, and Hairston aren’t even in their 50s. Perhaps there’s hope for them yet.   

Ben Joravsky discusses his reporting weekly with journalist Dave Glowacz at