19th Ward Ald. Matt O'Shea Won't Seek Reelection, Backs Chief of Staff Erin Ross

Ald. Matt O'Shea, who has held the 19th Ward seat on Chicago's Southwest Side since 2011, said he will not run for reelection in 2027, ending a City Council run of four terms representing Beverly, Mount Greenwood, Morgan Park and Washington Heights.

O'Shea, 57, told the Chicago Sun-Times this week that it was time for him to "step back and do something else." The announcement is a reversal from March, when he told Block Club Chicago he intended to run again.

"To do this job right, it's more than a full-time job. You don't have days off. You can't go to the grocery store. If there's a crime pattern or something happening in the neighborhood, it's very stressful. You have to be out front," O'Shea said.

O'Shea grew up in North Beverly, attended Christ the King elementary school and Mt. Carmel High School, and got his start in ward politics as an intern in the 19th Ward office under then-Ald. Ginger Rugai. He ran for the seat in 2011 after Rugai retired following 20 years in office. In each of his four elections since, O'Shea won with more than 60 percent of the vote, fending off a challenger every time.

O'Shea declined to debate his opponents during multiple campaign cycles, a stance that drew criticism from some rivals and residents but did not affect his margins at the polls.

O'Shea said he plans to endorse Erin Ross, his chief of staff, to take over the seat. Ross has worked in the 19th Ward office since 2024. Before that, she spent more than a decade as executive director of the 95th Street Business Association. Neither O'Shea nor Ross could be immediately reached for comment beyond what was reported.

O'Shea has been one of the more vocal critics of Mayor Brandon Johnson on the City Council. He helped push through an alternative budget in December 2025 that differed from the mayor's spending plan. Before Johnson took office, O'Shea had backed Paul Vallas in the 2023 mayoral runoff, announcing his endorsement at the South Side Irish St. Patrick's Day Parade that year.

O'Shea's decision makes him the third Chicago alderperson in recent months to say he won't seek another term. Ald. Marty Quinn of the 13th Ward announced in July he would not run for a fifth term, and Ald. Michael Rodriguez of the 22nd Ward said Wednesday he would not seek a third term. Each has cited different reasons for stepping aside.

The 19th Ward includes the bungalow blocks and brick two-flats of Beverly and Mount Greenwood. O'Shea and Rugai before him both ran offices focused heavily on constituent service and kept lower public profiles than some of their City Council colleagues. O'Shea's ward includes some of the city's more conservative-leaning precincts, and his relationship with City Hall's progressive wing has often been tense.

No date has been set for when candidates must file to run for the seat, but the 2027 municipal election cycle will determine who represents the ward for the next four years. O'Shea's endorsement gives Ross public backing from the incumbent as filing deadlines approach in the coming months.