Alderman’s Neutral Stance in Chicago Mayoral Contest a Disservice to 19th Ward

August 16, 2022

Assert yourself, Alderman O'Shea

When Pat Golden greeted throngs of supporters outside Saint Rita’s Shrine Chapel five days after his son Dan suffered a grievous injury on Beverly street, he remained cheerful when discussing his son’s condition and disposition.  

Moments later, when Mr. Golden directly addressed Chicago media, he managed to cope with considerable emotional turmoil to poignantly declare:

“This has to stop. This senseless violence of guns and shooting people, this has to end. And if we can't do it, then we have to vote people out of office.”

Words uttered with bitterness, despair, and anguish, though it is debatable to whom Mr. Golden was referring, a reliable hunch will conclude the retired Chicago Police homicide detective had Mayor Lori Lightfoot or Cook County State’s Attorney Kim Foxx in mind. As a resident of the Mount Greenwood neighborhood, it is also reasonable to presume Golden was also speaking of 19th Ward alderman, Matt O’Shea.

A lifelong resident of the 19th Ward, Alderman O’Shea has represented the Beverly, Mount Greenwood, and Morgan Park neighborhoods in the City Council since 2011.

A graduate of Christ the King and Mount Carmel High School, O’Shea attended Saint Mary's University in Winona, Minnesota, returned to Chicago and prior to his election to Chicago’s legislative assembly he served as an aide to former Cook County Sheriff Michael Sheahan and former Illinois State Representative Kevin Joyce. O’Shea also served as an office aide to former 19th Ward alderman Virginia Rugai.

Ordained by Rugai as her successor, O’Shea won his first aldermanic election in 2011 by defeating challenger Dr. Anne Schaible with 61 percent of the vote. Four years later, O’Shea again faced Schaible and increased his margin of victory by 11 points to return to office with 72 percent of the vote.

Running for re-election for a third term in 2019, O’Shea appeared in a candidate profile aired on WTTW. Attempting to build a groundswell for his return to office, O’Shea delivered trite references to investments in schools and on crime stuck to bland statements of fact:

“Public Safety will always be my top priority as your alderman. In the past year, overall crime in the 19th Ward is on a downward trend. We have seen a decrease in battery, burglaries, motor vehicle thefts, robberies. violent crime is down.”
“I love my community and am fully committed to working together with all of you to keep our neighborhood the best place to raise a family.”


O’Shea went on to thrash his election opponent, David Dewar, with 85 percent of the vote.

At the time of O’Shea’s second attempt to be returned to office, he had backed the mayoral candidacy of Jerry Joyce. A Beverly resident, former Assistant State's Attorney, and lifelong friend of the alderman, with O’Shea’s endorsement, Joyce ran away with the 19th Ward, earning over 9,000 votes. Despite Joyce’s impressive win in 19, his appeal across the whole of the city was slim, his campaign floundered, and he fell to seventh place after winning only four wards.

Less than a month after the February 26 election, with the April run-off between Lightfoot and Toni Preckwinkle looming, O’Shea ebulliently threw his arms around Lori Lightfoot, telling the Beverly Review:

Just sitting at the table across from someone, looking them in the eye, talking about issues that are important to our community, I had a real comfortable feeling. She (Lightfoot) was very candid. We talked about the issues important to us here, and I made a decision that I wanted to support her, and I really wanted to push hard here in the community to help get her elected on April 2.”


With the weight of O’Shea’s endorsement behind her, Lightfoot thumped Ms. Preckwinkle and carried the 19th Ward with 84 percent of the vote in a ward which outpaced voter turnout — 50 percent — against every other ward in the City of Chicago. O’Shea’s support for candidate Lightfoot, however, was pre-COVID, pre-summer of riots, pre-crime surge, and pre-Mayor Lightfoot.

Today, O’Shea sees things far differently: He sees crime as a knife permanently held to Chicago’s throat, pushing steadily against its jugular. Explaining Chicago under Mayor Lightfoot as a city riven by social violence and crime, and literally burning itself to the ground, O’Shea told the Sun-Times’ Fran Spielman:  

“The senseless violence is so pervasive across the city. And for people to say things like, ‘Murders are down’ [is insulting]. We’re a world-class city. I don’t know if we are anymore based on where we’re headed.”
“I’ve been very disappointed. My disappointment is the fact that public safety is compromised in this city. Crime is up. Perception of crime is up. Bad guys are winning.”


Oddly, Mr. O’Shea punctuated his forlorn outlook for Chicago not by directly pinning Chicago’s misery to Lightfoot, but by modestly declining to endorse Mayor Lightfoot a second time and adopting a neutral stance in the 2023 mayoral contest. A mixture of cunning and audacity, O’Shea’s “non-aligned” bearing for the 2023 mayoral race is an imprudent dodge intended to cloak his terrible error endorsing Lightfoot in 2019.

Let’s specify upfront, part of the record Alderman O’Shea has established during his three terms in the City Council is worth touting. Representing the 19th Ward distinctively, O’Shea has been fairly consistent supporting members of the Chicago Police Department, primarily as a co-sponsor of a bill which extended death benefits to families of officers who sadly took their own lives. In addition to this decent legislation, O’Shea has remained a strong supporter of the “Get Behind the Vest” campaign, and has hosted countless breakfasts which have raised over $300,000 for over 11,000 bulletproof vests distributed to officers.

Additionally, O’Shea has also earned plaudits for joining a small contingent of City Council members in opposition to financial settlements against the city. Outside the City Council, O’Shea has earned rightful praise for his civic mindedness through his commitment to the athletes and programs of Special Olympics Chicago.

Yet much like other politicians, O’Shea seeks to exalt his record and obscure his shortcomings. Keeping in mind all politicians are in the ego business, O’Shea, the politician, is always in pursuit of any opportunity to stand in the spotlight with the objective of being martyred. O’Shea does, however, have a few liabilities and the sum total of his record and actions are legitimate lines of inquiry.

For his endorsement of Lightfoot in 2019, a grateful Mayor Lightfoot rewarded O’Shea as chairman of the Committee on Aviation. A plumb chairmanship, if O’Shea’s term leading the panel is examined soberly, the 19th Ward alderman has established a rather unremarkable record.

According to Committee on Aviation meetings and notices, in 2021 alone, the committee met only four times. In a January 25, 2021, meeting, leasing agreements and noise issues at both O’Hare and Midway airports were discussed. In a February 25, 2021, meeting, an amendment to municipal code involved workers' compensation and other insurance claims at both airports was deliberated. In June 2021, enforcement and adjudication of violations to fire code at both airports were addressed. During the September 2, 2021, assembly, the committee chatted up concession agreements at O’Hare.

In 2022, the committee first met in March to have a chin wag over an amendment on an intergovernmental agreement with Illinois State Toll Highway Authority regarding the Elgin O'Hare Western Access Project. Two months later, on May 13, concession agreements crawled back onto the meeting agenda. One month after, on June 14, the panel met to chat about the replacement of copper lines with fiber optic lines as part of a Ground Lease agreement with Illinois Bell Telephone Company.

While the matters under consideration before O’Shea’s Committee on Aviation are worthy of discussion and deserve attention, they are insignificant when compared to other considerable issues at either O’Hare or Midway airports. For example: Fairness of airport contracts, gate modernization, addressing airline vacancies, safety or usage of passenger facility charges (PFC) have been ignored. Issues which deserve consideration and action, none appear anywhere on O’Shea’s meeting agendas over the past two years.

More broadly, apart from O’Shea’s lackluster administration of the Committee on Aviation, the 19th Ward alderman has established a less-than-stellar voting record on the City Council floor. Despite his “neutral” position in the 2023 mayoral race, a close examination of his voting pattern reveals O’Shea is in fact a stalwart supporter of the Lightfoot legislative program, casting votes with the mayor a staggering 78 percent of the time.

Apart from the fact O'Shea's votes in favor of Lightfoot's legislative agenda are inconsistent with the mores of many of his constituents, O’Shea’s obsequious allegiance to Ms. Lightfoot on Council legislation incredibly outpaces two of the chamber’s most obnoxious members, Democratic Socialist aldermen, Jeanette Taylor (20), and the orotund fake Byron Sigcho-Lopez (25), both of whom vote in favor of Lightfoot 73 percent of the time.

If O’Shea cannot come to a decision, 19th Ward voters will

Alderman O’Shea’s decision to remain uncommitted in the 2023 mayoral race is understandable, but it is still self-deceiving. O’Shea’s neutral stance rejects fulfilling obligations expected of an alderman.

Leadership is not entitlement and mistakes matter. Being an alderman means accepting a leadership role. Leaders do not pale before difficult decisions and they never flinch from responsibility. Good leaders live in the real world, work within truths, and appreciate reality. A capable leader is conscious of the fact voters take cues from them. A leader can shift strategy or tactics, but they can never abandon principles or obligations. Being an alderman is holding the powerful — in this instance Mayor Lightfoot — to account and promoting principled leadership.

O’Shea’s neutral position in the 2023 mayoral race is far from an airy impulse, but his non-position is not without reason. Though O’Shea publicly admitted a second endorsement of Lightfoot meant he would “have a civil war on his hands,” the central justification for O’Shea adopting neutrality rests with political survival and desire to hold on to power. O’Shea’s endorsement of Lori Lightfoot in 2019 hand delivered her the 19th Ward. In return, Lightfoot imparted the gift of the chairmanship of the Committee on Aviation to O'Shea in thanks.

Though O’Shea’s neutral stance is an implicit admission he blundered with his endorsement of Lightfoot in 2019, the alderman is making another mistake by laboring under the delusion Lightfoot could deprive him of his chairmanship for defecting in 2023. While a committee chairmanship is a rare gift and chairs enjoy the advantages of a budget and staff separate from aldermanic office, Mayor Lightfoot does not have the political strength to strip O’Shea from Aviation should she be returned to office. While O’Shea was nominated by Lightfoot to lead the committee, he was approved by a City Council resolution and his removal can only come from a new resolution and its approval by 26 aldermen.

Though no sensible alderman should take on Lightfoot blithely — the mayor is known for being petty, manipulative, and vindictive — Lightfoot has a knack for making enemies, she has exhausted political capital on the City Council floor, and it would be nearly impossible for her to orchestrate a coup against O’Shea.

While Alderman O’Shea’s neutral position is fathomable, it is still a misjudgment. An inexcusable shilly-shally, O’Shea’s neutrality is ambiguity. Ambiguity begets miscalculations. Miscalculations can be catastrophic, particularly at the ballot box.

Though Mr. O’Shea considers his non-aligned position for the mayoral race a shrewd political move, he is best served if reminded enthusiasm favors the dissatisfied and this is particularly applicable today. While the 19th Ward remains a desirable place to live, the beat of crime’s footsteps is beginning to echo throughout every corner of Chicago and the 19th Ward is learning it is not immune to crime’s harsh clutches.

Although crime in O’Shea’s ward has not reached unnerving levels found in other quarters of Chicago, a range of crimes — carjackings, burglaries, assault, and property crimes — are becoming grimly commonplace in the 19th Ward. Moreover, clues are abundant gang activity is becoming more prevalent in O’Shea’s ward.

If Alderman O’Shea has convinced himself the pose of neutrality in the 2023 mayoral election is a winning reelection strategy, he is committing another grave mistake. With Chicago in decline and a wave of crime washing over the city, residents in the 19th Ward are growing restless. Though O’Shea does enjoy the advantage of incumbency, he is not politically untouchable.

While it may be an overstatement to say O’Shea is vulnerable, rumor is rife two potential challengers are weighing bids to oust O’Shea next February. Though the power of incumbency grants protections, it does not render officeholders invincible so the notion two potential election opponents are holding an executioner's sword aloft can hardly be comforting for the alderman.

19th Ward residents’ patience is wearing thin

Running away from an unpopular incumbent mayor is a predicament with which politicians have wrestled since time immemorial. A vexing problem for the alderman, O’Shea opting to sit on the sidelines has only revealed himself to be embarrassingly weak-kneed.

Voters in the 19th Ward elected Mr. O’Shea due to his personal authenticity and by virtue of a practical intelligence and common sense he shares with residents. While O’Shea can credibly claim he has helped the ward’s public schools and commercial interests on 103rd and 111th Streets, crime hovers menacingly in the background. This is the one issue O’Shea cannot massage until it coughs up data he can spin to residents.

Voters in 19 are willing to brook what they now view as O’Shea’s mistake endorsing Lightfoot’s candidacy in 2019. Nonetheless, residents in Beverly, Mount Greenwood, and Morgan Park will only tolerate O’Shea making this mistake once. Mr. O’Shea is at a crossroad, but there is a way from him to wiggle out of this mess. Alderman O’Shea can, on one hand, choose self-interest for the preservation of his chairmanship of the Aviation Committee by remaining the perfect idler and refusing to endorse a mayoral candidate. O’Shea could, on the other hand, create distance from Lightfoot and publicly embrace the mayoral bid of his City Council colleague, Alderman Ray Lopez (15). A man who has defied threats from Satan Disciples, Lopez has demonstrated an independence and honesty unfamiliar to Chicago politics.

Regardless of the option on which Mr. O’Shea eventually settles, both are certain to come with some political risk. However, O'Shea should keep in mind voters, not Mayor Lightfoot, placed him in office. Voters in 19 can remove O'Shea from office. Should Mr. O’Shea remain uncommitted in the mayoral race, he may retain his chairmanship of the Aviation Committee, but he will reveal his impulse to serve as alderman only at intervals and incur the wrath of 19th Ward voters. If Mr. O’Shea disavows Lightfoot and supports the candidacy of Alderman Lopez, he will redeem himself in the eyes of residents and demonstrate the kind of political courage and independence 19th Ward voters expect from their alderman.

Alderman O’Shea gift wrapped the 19th Ward for Lori Lightfoot and it helped her goose step into City Hall in 2019. Mayor Lightfoot returned the favor by creating one of the greatest catastrophes Chicago has ever seen. With Chicago at an all-time low, Alderman O’Shea can either linger on the political margins or he can play a pivotal role in helping Chicago recover from the disastrous Lori Lightfoot experiment.

Should Mr. O’Shea choose an active role and campaign for Alderman Lopez, 19th Ward voters may be inclined to reward him with another term and perhaps someday erect statutes in his honor for saving Chicago from another Lightfoot term.

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