
Friends and colleagues are remembering longtime Pioneer Press reporter Irv Leavitt, who covered Chicago’s North Shore suburbs for nearly 30 years, as a tenacious journalist, generous mentor and champion of old-school reporting.
Leavitt, 70, died June 13 in Chicago after battling cancer and several other illnesses in recent years, according to his daughter, Megan Leavitt.
Leavitt was a fixture on the North Shore, reporting for Pioneer Press in numerous communities while winning several of the Chicago Headline Club’s Peter Lisagor Awards, which are the prestige award for Chicago-area journalists.
“He understood people and could interact with anybody whether it was a government official or someone he had to talk to to write an obituary for a loved one or talking with quirky people where some of us other reporters wouldn’t have taken the assignment, but he did,” recalled retired Pioneer Press reporter Kathy Routliffe. “When he put it together, it was well-sourced and extremely well written.”
Lynne Stiefel, another former Pioneer Press colleague, offered a similar perspective.
“Irv brought a unique point of view to every story he wrote,” she said. “When I filled in as an editor I found Irv’s stories so packed with information that it sometimes hurt to cut them down.”
Leavitt was raised in the Chicago area as the family moved frequently between the city and suburbs, according to his daughter.
After graduating from the now-closed Niles East High School, Leavitt attended the University of Illinois at Urbana-Champaign before transferring to the University of Illinois Chicago.
Following college, he operated a bookstore in Rogers Park and was also a cab driver.
“He really liked talking to people,” said Megan Leavitt, a potter and illustrator in Minneapolis, of why he enjoyed cab driving.
Megan recalled her father telling her about picking up a passenger at O’Hare International Airport who said he had never seen snow. Leavitt pulled over and showed him how to make a snowball.
Yet, journalism remained a calling. After working for the Daily Illini in college, Leavitt joined Pioneer Press in 1989, where he would spend nearly three decades covering North Shore communities.
“One of the things that made him a good reporter is that he was never afraid to ask uncomfortable questions and even when people responded badly, he had a sense of charm that could calm down people,” Routliffe reminisced.
Leavitt produced a large number of articles per week for the newspaper chain, often coming up with unconventional stories. In one feature known as “The Unemployee,” he would chronicle his attempt to do someone else’s job for a day.
As technology evolved, he produced online videos for the news organization augmenting his stories.
While he was known for asking difficult questions, he earned respect from those he queried.
“While he was always looking for the next story, he never treated me with anything but respect and always fairly,” noted former Northbrook Village President Sandy Frum.
“If I was honest with him, he would be the same with me. And he respected my boundaries, the things I could or couldn’t tell him. I will always remember him as a great local reporter, who was such an asset to the community.”
Back in the newsroom, Leavitt mentored many younger reporters on how to go about getting stories.
“Irv was a natural born story teller, and his Lisagor Awards are proof of that,” added Rick Kambic, who now serves as director of communications and community engagement at Fenton High School.
“I loved seeing all the tiny details he would incorporate into an article or column that brought the story to life in my brain. I did my best to emulate that skill, and show my readers what made the subject of my article so special or important.”
Beyond reporting, Leavitt was active in the Pioneer Press newspaper guild during a period of significant change in the newspaper industry
“As much as Irv was a valuable watchdog of local governments, he was also a staunch union member who stood up for colleagues when our own company would lose perspective on our mission. His tactful choice of words and charming charisma was very helpful in negotiations and when advising our members on potential realities of a situation,” noted Kambic, who later became chairperson of the Pioneer Press bargaining unit.
While working as a reporter, Leavitt occasionally continued driving a cab as a side job. During one shift he met Helen Gallagher, a speech pathologist with Chicago Public Schools. The chance encounter led to a lasting relationship and the birth of their daughter, Megan, in 2000.
However, Gallagher lost her own fight with cancer in 2011, leaving Leavitt as a single parent with a young daughter. He cared for her even as he often had to work unconventional hours due to the evening nature of municipal meetings.
Determined to continue doing his job, Leavitt frequently brought Megan along to the often-arduous meetings, where she would bring a sketchpad.
“I got to draw a lot of people arguing about city planning,” she quipped.
Leavitt left Pioneer Press in late 2017, but remained in touch with many of his colleagues.
“He came to my July 4th barbecues every year with Megan and he was always a lot of fun,” Stiefel said.
He also remained professionally active in many of the communities where he had been a reporter as he did some public relations work and volunteered for the Northbrook Farmers Market. He also penned a freelance column for Chronicle Media and wrote a Substack blog.
Leavitt became particularly interested in a grassroots movement to change Skokie’s electoral system, seeking to make the process more competitive and non-partisan. It would later become known as the Skokie Alliance for Electoral Reform. He wrote about it frequently in his online column.
“His writing was excellent,” said Gail Schechter, who was the movement’s organizer and today is a Skokie village board trustee.
“He really put our electoral reform movement on the map. He came to our first meeting and we didn’t have a name yet and he just captured it and it really helped us. If we didn’t have that, I don’t think we could have really been out there about what the problems were in Skokie.”
Later referenda on the issue passed.
Schechter added Leavitt also wrote frequently on affordable housing efforts and civil rights-related issues.
His interests and hobbies included baseball, reading Nelson Algren novels, Chicago history and cooking.
Megan Leavitt is the only immediate survivor. Per her father’s wish, there will not be a formal memorial service. However, an informal celebration of life is set for Sunday, June 21 from 6 to 10 p.m. at Black Sheep Chicago, 2535 W. Peterson Ave., Chicago.




