Recently, we did a post about the most progressive wards in the city. Now, we’re going to take a look at the city’s most conservative wards. What makes a ward conservative? Two criteria: It voted for Paul Vallas by a large margin, and it contains precincts that voted for Donald Trump in 2020. Also, in most cases, a lot of cops and firefighters live there. 

11th Ward

For decades, the 11th Ward has been controlled by the Daley family. The Daleys put a lot of Bridgeport residents on the city’s payroll — 2,000, by the estimate of Mike Royko in Boss, his biography of Richard J. Daley. City workers tend to be conservative.

The Daleys are still in charge here. County commissioner John Daley is ward committeeman. His nephew, Patrick Daley Thompson, was alderperson from 2011 to 2022, when he was convicted of lying to federal regulators about a loan from a Bridgeport bank. The Daley family supported the appointment of his replacement, Nicole Lee, a Chinese-American. Bridgeport was long a white enclave in the middle of the South Side, but Asians are now a plurality here. They seem to have inherited their predecessors’ political attitudes.

Trump won two precincts in Canaryville, at the southern end of the ward, and another in Armour Square. Vallas won 73 percent of the vote in the 11th Ward. On a precinct-level map of the mayoral election results, the Dan Ryan Expressway was a dividing line between Vallas and Johnson voters. Mayor Daley allegedly placed it there to act as a barrier between Bridgeport and the Black Belt. It plays that role to this day.

13th Ward

On the wall of Cafe 63, Clearing’s neighborhood diner, is a collection of buttons advertising the neighborhood’s political allegiances over the decades: Say No to Washington, Irish for Reagan Bush, Vrdolyak ’89, Daley for Mayor.

Clearing is a political neighborhood, says owner Dale Andrews, because “you go down any block, there’s 10 houses owned by city workers.”

Politically, the neighborhood is “heavy Democrat,” Andrews said, but these are Democrats of an older school than one might find at a United Working Families rally. “The one hand washes the other principle. That’s been going on in this neighborhood since the ’40s and ’50s. Not as heavy as Bridgeport, but no place is as heavy as Bridgeport.” 

As Cafe 63’s button collection indicates, Clearing’s voters are conservative Democrats, who vote for their party on a local level — they elected Michael Madigan to the legislature 25 times — but will abandon it at the national level for a Republican who better suits their social views. Latinos have been moving into Clearing in recent years, but they haven’t made it all the way to the city limits. Every precinct west of Narragansett Avenue voted for Donald Trump in 2020. Latinos have spoken anxiously of seeing Trump flags dangling above stoops.

The 13th Ward’s alderperson is Marty Quinn, a wholly owned subsidiary of Madigan, who has been committeeman of the 13th Ward since 1969, and controlling everything that happens here. Madigan learned politics from the first Mayor Daley, and made a practice of meeting with his precinct captains every Saturday morning. Madigan and Quinn are so close they share office space on Pulaski Avenue. Quinn rarely speaks in City Council meetings, but his influence is seen everywhere in his ward. The windows are bungalows and bars are filled with placards proclaiming “Our Family Supports Marty Quinn.”

19th Ward

Isabel Wilkerson, author of The Warmth of Other Suns, called Mount Greenwood “an insular, Leave It to Beaver world where white people can live out entire lives without ever getting to know a black person, where people rarely venture beyond understood borders.” Writing in the Chicago Reader, Jake Malooley called it “Chicago’s Upside Down:” “No demogorgon roams this parallel universe, but a majority of its electorate did back the man who’s been called the swamp monster: President Donald Trump.”

Mount Greenwood did love Trump — he won one precinct by 49 points — but it loved Paul Vallas even more. A few weeks before the mayoral election, I met a firefighter named Tommy in the Blackthorn Pub on 111th Street. He didn’t know a single person who was voting for Brandon Johnson: “I don’t think he’s (Vallas) our best choice, but he’s the only choice for this election, because of the safety of the neighborhoods, and how what’s-his-name is going to treat the police department. City workers, it’s our last resort to live in safety. I would say the balance of the city depends on this election.” If Johnson wins, he said, “there’s probably going to be a rush of people leaving.”

It’s not surprising that the firefighter didn’t know any Johnson voters: In the precinct where the Blackthorn Pub is located, Vallas got 95 percent of the vote, winning 458-24. The quintessential Mount Greenwood bungalow was adorned with an American flag, a statue of the Virgin Mary, a Vallas for Mayor sign, and a “We Support DG #FIGHTLIKEAGOLDEN,” in honor of Danny Golden, a Mount Greenwood police officer who was shot and paralyzed while breaking up a bar fight in Beverly. The neighborhood raised $1.5 million to assist Golden in his recovery.

Mount Greenwood has not experienced a murder in years, but like most Trump supporters, its residents are nostalgic for what they see as a better, safer time.

“There has been attempted carjackings, robberies,” said the owner of MG Embroidery and Screen Printing, which displayed a “Police Lives Matter” hoodie in the window. “When I was a kid, we used to have beat cops in this neighborhood. Now, out of nowhere, gone.”

41st Ward

The 41st, on the Far Northwest Side, has traditionally been the most Republican ward in Chicago. From 1973 to 2019, it was represented in the state House of Representatives by a pair of Republicans: first Roger McAuliffe, then his son, Michael. The current representative, Rosemont Mayor Bradley Stephens (son of Rosemont mayor Donald Stephens), is also a Republican. (In Chicago, even Republicans keep offices in the family.)

Brian Doherty, who was alderperson from 1991 to 2011, was the City Council’s lone Republican during that time. The current alderperson, Anthony Napolitano, has variously called himself a Republican and an independent. Along with Nick Sposato, his neighbor in the 38th Ward, Napolitano is part of a two-man caucus of conservative Italian-American firefighters. (Napolitano and Sposato also have the thickest Chicago accents on the Council.) During his re-election campaign this year, Napolitano declared his support for the police and his opposition to “unwanted high-density residential developments” that would threaten “the character of our single-family home neighborhoods.” Wedged between Niles and Park Ridge, the 41st Ward is a suburb in the city.

In the 2020 election, most of the precincts north of Touhy Avenue in Edison Park voted for Trump. I recently dropped in on a block party on the 7300 block of North Oriole Avenue and found out why. It was a small-townish scene: American flags and Back the Blue flags drooped above the stoops of bungalows, country music keened from a speaker, children jumped inside a bouncy castle. Everyone was a cop, a firefighter, or related to a cop or firefighter. Cops are conservative, wherever they work. The profession attracts conservatives: It’s a paramilitary organization concerned with hierarchy and enforcing law and order. (The teaching profession, on the other hand, attracts liberals, since it’s concerned with inquiry. In this year’s mayoral election, the teachers beat the cops.) For the most part, Chicago’s most conservative wards are the city’s Copland. Vallas won 86 percent of the vote here, his best percentage of the city.

50th Ward 

The 50th Ward is an outlier among Chicago’s most conservative wards. It’s not conservative because it has a large population of police officers; it’s conservative because it has a large population of Orthodox Jews.

West Ridge is best known for the Indian and Pakistani restaurants on Devon Avenue. But cross California Street (to quote the title of West Ridge native Adam Langer’s novel Crossing California), and you enter a world of synagogues, kosher bakeries, and Hebrew bookstores. Orthodox Jews have settled here so they can observe their Sabbath laws by walking to shul on Saturdays. In 2020, a precinct near California and Pratt voted for Trump by 44 points. (West of California, the only Democratic precincts were in the Winston Towers, which are populated by Jewish retirees. And Joe Biden’s percentages were only in the 50s there.)

According to the Times of Israel, Orthodox Jews are attracted to Trump because of his support for Israel: “The moving of the US embassy to Jerusalem; recognition of the Golan Heights as being under Israeli sovereignty; recognition of Israeli legal rights in the West Bank settlements; withdrawal from the Iran nuclear agreement which was much opposed by the Israeli government; the drafting of peace proposals which were very favorable to Israel; and the forging of normalization deals between Israel and three Arab states are cited frequently by modern Orthodox proponents of Trump as a reason to keep supporting him.”

The 50th Ward is represented on the City Council by Debra Silverstein, an Orthodox Jew, but a Democrat. Silverstein is Democratic ward committeeperson, a job she inherited from her ex-husband, Ira Silverstein, a former Democratic state senator.