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Lightfoot’s ex-deputy mayor of public security to John Kass: I pack heat on the CTA

Former deputy Chicago mayor John O’Malley

This relatively long article covers three different topics related to conservative pundit John Kass, previously known for his anti-bike columns in the Chicago Tribune. If you're short on time and are mostly interested in the news item mentioned in the headline, skip ahead to the last section of the post.

John Kass' history of bike-baiting

Longtime Streetsblog Chicago readers are familiar with the many anti-bicycle columns conservative former Chicago Tribune writer John Kass published in the paper in the early 2010s, arguing that the so-called "Little Bike People" aren't operating "legitimate vehicles." Therefore, he said, the city shouldn't invest money to protect them with safe bicycle infrastructure, or encourage more cycling through the Divvy bike-share system.

But Kass clearly crossed a line in a 2013 column suggesting that drivers who injure or kill bike riders by opening a car door in their path shouldn't be held responsible. That was despite the fact that Chicago motorists had killed multiple people on bikes that way in recent years. Since then drivers have seriously injured or killed several other people biking.

John Kass
John Kass
John Kass

"If we dare open our doors when a bicyclist is approaching, and said bicyclist hits the door," Kass wrote, "[Will it be] the fault of the Little Bike People? No. It’ll be the fault of the drivers of legitimate vehicles. And they will pay."

Dustin Valenta, a courier and actor who nearly lost his life in a dooring crash on Milwaukee Avenue, effectively called Kass out in a Streetsblog interview. "He’s clearly writing from the stance that bicyclists are in the wrong in the first place, just by being on bikes," he said. "It’s like he’s putting a value on human life based on an individual’s choice of transportation. I just think that it’s sad that he’s drawing a line in sand, as if there’s a difference between human beings in cars and human beings on bikes... [Dooring fines are] not about punishing drivers and rewarding bikers; it’s about making sure everybody is safe." That was pretty much the end of Kass' anti-bike schtick.

Fast-forwarding several years, in July 2020 Kass wrote an op-ed arguing that billionaire George Soros was "flying under the radar" undermining public safety in Chicago and other big cities, which was denounced by ADL Midwest for "feed[ing] antisemitic conspiracies," and his column was soon moved off its showcase position on Page 2. After the paper was bought by a hedge fund, in June 2020 Kass took a buyout, and since then he's continued to blog and do podcasts, generally steering clear of sustainable transportations topics.

Recent Kass-Greenfield interactions

I usually try to keep my extracurricular activities separate from my Streetsblog work, but if you'll indulge me, I'd like to make an exception here. Those who follow my personal Twitter account have have noticed that John Kass and I have (indirectly) exchanged some words recently.

In June a tipster informed me that after writing a column in May 2020 about moving back to Chicago after decades in the suburban Western Spring, Illinois, Kass quietly fled the city in response to civil unrest during the George Floyd protests. He resettled in Saint John, a town about 21,000 people in Northwest Indiana, surrounded on three sides by farmland. That means Chicago's and Illinois' most prominent right-wing pundit doesn't pay income or property taxes here, and can't even vote for or against the local politicians he critiques.

Saint John, Indiana
Saint John, Indiana. Image: Google Maps
Saint John, Indiana

I had fun publicizing that fact on social media. The Tribune recently did a full writeup of Kass' move, crediting me with breaking the story.

Then on Saturday, July 23, I took a Red Line + bike + South Shore Line day trip to Saint John to get a sense of what the town is like, live-tweeting thoughts and photos, as I've done on other bike adventures. I had a good time there, including sampling a northwest Indiana-style (the area is nicknamed "The Region") smash burger from Schoop's Hamburgers, and visiting the Bill Kurtis-narrated Shrine of Christ's Passion sculpture path, a nicely landscaped facility with artwork depicting the Stations of the Cross.

My findings were that Saint John feels like a suburban bedroom community – basically all of the retail is located on Highway 41, the five-lane road that bisects the town. Judging from my conversation with a Schoop's employee; the presence of "Go Cubs Go" and "The Superbowl Shuffle" on the burger joint's jukebox; a Bears jerseys sighting; and Chicago-style hotdogs on the menu at Avgo, the local Greek-owned diner, most locals seem to identify as Chicagoland residents. (The center of town lies just outside Streetsblog's proposed boundaries of the Chicago area, which include all locations within ten miles of a Metra or South Shore Line station, and on Central Standard Time.)

Aerial view of central Saint John. Image: Google Maps
Aerial view of central Saint John. Image: Google Maps
Aerial view of central Saint John. Image: Google Maps

As such, I concluded that it's not completely absurd for John Kass to spend most of his time opining about politics in Chicago and Illinois, even though he's technically a Hoosier nowadays.

Still, Kass was not pleased by these developments, and responded by bitterly attacking the Tribune and myself in at least four blog posts and podcast appearances in the past week. In one post he referred to yours truly as a – wait for it – the "lefty troll rep of the Little Bike People," which was sort of funny.

Image: Russell Mast via Crayon
Image: Russell Mast via craiyon
Image: Russell Mast via Crayon

However, Kass also accused the Trib and me of "doxxing" him, which was inaccurate. Simply reporting the name of the town where a public figure lives doesn't really fit the dictionary definition of that term: "publishing private information about someone."

Worse, Kass falsely stated in a podcast (at 47:00) that I "issued a series of tweets, 'I’m almost at Kass’ house, I’m almost here,' taking pictures on [my] way out to [Kass'] place." He doubled down on that untruth in one of last week's blog posts, writing that my trip to Saint John involved "traveling to [his] home."

(I realize that I'm rewarding Kass' less-than-honest behavior with clicks by linking to his stuff, but it's important to set the record straight.)

Thankfully, Kass' fellow former Tribune columnist Eric Zorn debunked Kass' claim that I visited, or threatened to visit, his house on Zorn's blog The Picayune Sentinel. "[Greenfield] was not traveling to Kass’ 'home,'" Zorn wrote. "Indeed the first entry in the Twitter thread that chronicled his trip to Saint John contained the assurance, 'No, I won't identify or visit Kass' house.' And he didn't."

Actually, my full statement was "No, I won't identify or visit Kass' house – I don't want to get shot." That turned out to be a wise decision, because in another one of Kass' podcast appearances last week (at 7:00) he implied that he would have, in fact, responded with violence: "[Come to] my house and we'll see what happens to you. OK?" Of course, that contradicts his earlier claim that I was guilty of "traveling to [his] home." But accuracy was never John Kass' strong suit.

Ex-deputy mayor John O'Malley and his CTA Smith & Wesson

While I said Kass usually doesn't discuss walking, biking, or transit nowadays, by coincidence this week was an exception. Kass hosted Mayor Lori Lightfoot's former deputy mayor of public safety John O'Malley on one of his his podcasts, and they had an extended discussion of the recent spike in violent crime on the CTA, and the best ways to address it. That conversation starts around 26:00.

We've talked about CTA crime extensively on Streetsblog. I believe existing Chicago transit policing has its place. However, events such as the 2020 shooting of a man officers tried to detain for illegally walking between 'L' cars, which ended with the police recklessly firing up the escalator of a bus downtown station, suggest that adding more guns to the system is not the solution. Holistic approaches to improving safety on trains and buses include well-trained unarmed Transit Ambassadors; more funding for mental health services and housing the homeless; and improving CTA reliability, which will boost ridership and "eyes in the cars," a natural crime deterrent.

Unsurprisingly Kass and O'Malley, a former chief deputy U.S. Marshal who left the Lightfoot administration after just one year on the job, favor increased policing of Chicago transit.

O'Malley sat on the Chicago Police Board back when Lightfoot was board president, and he was the only one of the nine board members to oppose the firing of Officer Daphne Sebastian, one of the cops accused of covering up the Laquan McDonald police murder. He currently works as director of global corporate safety and security for the John Blair company.

Police officers at the Jackson Red Line station. Photo: John Greenfield
Police officers at the Jackson Red Line station. Photo: John Greenfield
Police officers at the Jackson Red Line station. Photo: John Greenfield

O'Malley argued on Kass' podcast that the Chicago Police Department's CTA detail is "depleted" and should be increased to 100-150 officers, "where they're visible on these train lines, on these bus lines, where they're providing the safety and security that CTA riders are entitled to."

Here's a telling exchange from their conversation, lightly edited for brevity and clarity.

John Kass: I don't know who in their right mind wants to get on the 'L' now. I just don't.


John O'Malley: I'm a frequent Blue Line rider, which is... one of the safer lines.

[Anecdotally, from scanning CTA headlines every morning, my sense is that the vast majority of Chicago's violent transit crime takes place on the Blue and Red lines, the only 'L' routes that run 24 hours.]

JK: You have the look. You have the look, OK? If I see you sitting on the corner, just minding your own business, you're not staring into the cell phone. You got those O'Malley eyes scanning the perimeter all around you.

JOM: I take pictures of people standing on the platform and on the train that I use in situational awareness training. As great as an invention the cell phone is, for situational awareness it's the worst thing that we got goin'. 'Cause people pay zero attention to their surroundings, not only on the CTA, but just in general.

Yeah, and I also have a little friend when I ride the train, and when I'm out and about it the city of Chicago...

JK: Is his name SIG [Sauer, a German firearms company]?

JOM: No, it's S and a W [Smith & Wesson, an American gun manufacturer.]

O'Malley's last statement is a remarkable revelation, since it's not clear whether it's legal for him to tote a gun on the train. In 2013 Illinois lawmakers passed concealed carry legislation that banned concealed firearms on the CTA.

The CTA Rules of Conduct currently has a passage prohibiting "Possessing or carrying any weapon including, but not limited to, guns, clubs, knives, stun guns, tasers and explosive devices. This does not apply to those individuals authorized under Section 5/24-2 of the Illinois Criminal Code to carry weapons onto transit or to pepper spray."

I asked the CTA and O'Malley's current employer John Blair whether he's authorized to carry a gun on the CTA, but didn't get responses by press time.

In addition I discussed the subject with a veteran Chicago news reporter, who doubted that simply being a former deputy mayor means you're allowed to carry a strap on the 'L'. "He could very well have some authorization I'm not aware of. But I think the lack of response by his employer and CTA tells you he doesn’t have the authorization to carry."

But wouldn't it be foolish for O'Malley to publicly discuss carrying a gun on transit if it's illegal for him to do so? Surely he's got more sense that that.

The reporter responded, "O’Malley is a pretty dumb guy."


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