Can Mike Cummings Upend Matt O’Shea in Chicago’s 19th Ward?

February 7, 2023

Beverly, Mount Greenwood, and Morgan Park deserve an alderman better attuned to the needs of residents

Ask Mike Cummings why he is sacrificing the comfort of retirement to seek the seat representing the 19th Ward in the Chicago City Council and he will tell you he feels compelled to run.

A former homicide detective with the Chicago Police Department (CPD), with the exception of a brief interlude in which his family lived in Evergreen Park, Cummings has resided in the 19th Ward his entire life. Casting his mind back to his youth, Cummings recalls with affection a 19th Ward blessed with some of Chicago’s grandest homes, leafy lanes, pretty parks, independent shops, and cozy restaurants. It was a neighborhood in which Cummings says generations of families could find tranquility and was amply appealing for them to settle and live out a golden life.

Ruminating over his decades in adulthood as a resident of Morgan Park, Cummings tells of a time in which the 19th Ward’s commercial corridors flourished, sweeping parks and playgrounds were once filled with children, and evenings which were reserved to socialize at Western Avenue tap houses.

“Not anymore,” Cummings laments, “the leadership over this ward just isn’t there.”

Describing the 19th Ward’s agonizingly slow evolution from a stable, congenial neighborhood to a community which is now experiencing a marked increase in crime and economic instability, Cummings assigns blame on Alderman Matt O’Shea’s visionless leadership.

Raising the issue of the alderman’s performance in his three terms in the City Council, Cummings points to O’Shea voting fairly consistently with Mayor Lightfoot — some 78 percent of the time — and describes O’Shea casting ballots with the mayor’s legislative priorities as “inconsistent” with a majority of ward residents. On 19th Ward matters, Cummings expresses frustration over how 311 requests under the incumbent alderman require an excessive amount of time to complete. “Ward work shouldn’t be a chore for an alderman,” Cummings says.

Aside from O'Shea's voting record and inattentiveness to ward issues, Cummings describes with displeasure O’Shea’s tendency to remind audiences about the various social maladies or the need for police on streets when addressing media, yet the alderman is silent in moments when the powerful — mainly Mayor Lightfoot — should be held to account. Problems which he says should have elicited strong responses and direct criticism of Chicago’s leaders from the incumbent alderman, Cummings says O'Shea publicly demanding Mayor Lightfoot take bold and decisive action is not the incumbent's “strong suit.”

Explaining O’Shea has become detached from the concerns of the residents, Mr. Cummings believes much more is expected from a public official and an alderman serving the 19th Ward must welcome the demands of the office.

"The alderman (O'Shea) could and should have used his position in the City Council to place blame where it belongs. Their (Mayor Lightfoot and Superintendent Brown) policy positions have caused a terrible decline in Chicago. He’s got a committee chairmanship, perhaps that’s why he hasn’t called into question Mayor Lightfoot’s mismanagement of our city. This isn’t leadership. It’s complacency."

The 19th Ward’s revival, Cummings says pointedly, “only comes with a change in leadership.”

A graduate of Queen of Martyrs, Brother Rice High School, and Saint Xavier University, Mike Cummings spent 35 years serving Chicago as a member of the Chicago Police Department. Entering the department in 1986, Cummings served with the Bureau of Patrol, was briefly assigned to the Special Operations Section (SOS), and spent 22 of his last 24 years as a homicide detective.

Lured into investigative work by the challenge of unknotting complicated murder cases, Cummings distinguished himself by conducting meticulous criminal probes —sometimes at considerable risk to himself — many of which culminated with the removal of predators and murderers from the streets. Tasks performed with skill and determination, Cummings brought criminals to justice, and both closure and solace to the victims and their families in countless cases.

To solve such crimes requires a multitude of personal and professional talents: Patience, a capacity to delegate authority, decision making, intelligence, and both organizational and managerial skills. Above all, it requires leadership.

After 22 years grappling with complexities of homicide investigations, Cummings was promoted sergeant, and returned to the streets for the final two years of his career. Upon completion of his 35-year career serving the Windy City, Cummings had established an admirable record as a peace officer, earning 14 commendations for exemplary conduct and another 92 honorable mentions for his devotion to duty. In 2016, Cummings and fellow detectives were honored with the Chicago Crime Commission’s Law Enforcement Excellence Award for unraveling the mystery surrounding the shooting death of 9-year-old Tyshawn Lee. A case which galvanized the national press, Cummings led the investigation into the youth’s death. Calling it one of the higher achievements of his career, Cummings’ resourcefulness and unrelenting pursuit of Lee’s murderers ultimately led to three men convicted of the crime.

Unfinished with serving Chicago, Cummings is now seeking a seat in the Chicago City Council and he plans to fulfill the role of alderman as it was intended: A platform to represent the best interests of 19th Ward residents.

A homeowner and business owner in the 19th Ward, Mr. Cummings aims to restore Chicago to fiscal sanity by gradually slowing borrowing, modestly trimming the budget, and devising need-based annual budgets which adequately fund critical governmental services.

To boost the commercial strips in the ward, Cummings supports a Special Service Area (SSA) tax to pay for supplemental services. To raise revenue, a percentage of which would be set aside to address Chicago’s acute pension crisis, Cummings is weighing the introduction of video slot machines in businesses across Chicago. To uplift the 19th Ward’s economy, Cummings is pledging his full cooperation with civic groups in the community.

An experienced peace officer, Cummings believes defeating crime in the 19th Ward and throughout the City of Chicago can be attained, while simultaneously holding members of the Chicago Police Department to the highest professional standards of law enforcement.

A man who believes the pathway to success for Chicago’s pupils begins with strong schools which educate and inculcate good work habits, Cummings has a strategy to revitalize Chicago schools and return neighborhood schools to learning centers: Reform. Cummings says schools in the 19th Ward and across the city are not living up to their promise. With academic performance listless in some schools, Cummings maintains the time has come for Chicago’s public school system to become accountable. Though Cummings acknowledges sufficient funding is essential, reform is critical to improve student academic progress.

Accompanying reform, Cummings states the time has also come for vocational training to be rehabilitated from its unjustified ignominy. An accommodation for students who decide against enrolling in college, Cummings is advancing a plan to return and expand Career and Technical Education (CTE) curriculum to the Chicago Public Schools (CPS). This would also call for the hiring of certified staff and educators to lead classroom instruction. Once a mainspring of Chicago’s secondary schools, the dramatic reduction in CTE course offerings consigned CPS students opting against enrolling in a four-year college or university to a life without acquiring “soft-skills” in demand in today’s labor market.

Training which can ripen into an attractive career upon graduation, CTE, which includes specific career-oriented classes, internships, apprenticeships, and in-school programs created to enrich post-school work readiness, would be blended with core academic skills to further augment student learning.

The 19th Ward has reached a critical juncture. Though the ward once sent consummate legislators to represent the neighborhood in the City Council, today the 19th Ward has lost the tangible influence it once exercised over Chicago. The 19th Ward deserves an alderman who comprehends the priorities of the ward and attends to its needs. Mike Cummings is a man of independent judgment and strong resolve who has built a campaign around a message of unity of purpose among constituents and a shared vision for Chicago.

A father of three and grandfather to seven grandchildren, Cummings lives in Morgan Park.

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