Review: Windy City Watchdog

Windy City Watchdog by Bob Wiedrich
My rating: 3 of 5 stars

This Chicago reporter’s memoir follows in a surprisingly substantial niche genre. From Ben Hecht on, it’s been a kind of late-career obligation for Chicago’s top muckrakers to reflect on their lives, careers, and favorite anecdotes. I got curious and combed my shelves for others in the tradition: I already have John McPhaul’s Deadlines & Monkeyshines (1962), Bill Doherty’s Crime Reporter (1964), and John Drummond’s Thirty Years in the Trenches (1998), and I’m not even including the late career retrospectives that Ed Baumann and John O’Brien put together. With that, I’m sure missing plenty more. Narrow as it is, it’s been fertile ground.

So, in that light, I find it kind of sad that Wiedrich’s memoir is self-published and that’s it’s gotten very little attention. Some of that, I’m afraid, is his fault. This is written in short, episodic bits. It feels like an assemblage of columns he’s written in retirement more than a coherent narrative. But some of that is a world that, as we see so dramatically with the crisis over “fake news,” has forgotten the work it takes to do real reporting. A generation ago, there’d have been a real market for something like this.

I’ve been doing a lot of digging in mid 1970s Chicago crime reporting (for a project that’s kept me from doing much other reading), and there’s no question Wiedrich was a real star. Alongside his Tribune partner Sandy Smith and the Sun-Times’ great Art Petacque, Wiedrich was the premier reporter of gangster events of his era. His old columns make sense of stories that others were putting together only in piecemeal. There’s a saying that journalism is the first draft of history. In those days, Wiedrich did his share of those first drafts, but he may have been alone in also doing a kind of second-draft, of writing pieces like his awesome “The Old, Gray Mob, It Ain’t What it Used to Be” in 1974 as a careful look at the way the founding generation of Chicago’s Syndicate was dying out. As someone going back to make sense of the period, I find his work is essential.

This memoir is not, for the most part, as spot-on as those old columns. I enjoy the way he captures a kind of gentle corruption permeating the Chicago he remembers. He has a great story about trying to tip a cop off about a bookie joint as a kid, only to be told to mind his own business. Or he talks as well about how, as a nearly broke young reporter, he’d join cops for free meals from restaurants that knew they were being gently squeezed.

I picked this up for the nuggets I might get on the gangsters he covered and knew, and I’m afraid it’s often thin in that department. There’s a sameness to most of the Syndicate members he discusses, though he clearly hated Richard Cain, a sheriff’s deputy who notoriously worked for the Syndicate at the same time. (And wound up shot in the end.) Cain once tried to entice him into a sexual encounter with a prostitute in an effort to collect dirt on him for future blackmail. Otherwise, we get a lot of names but none of the only-now-it-can-be-told details that I was hoping for.

There are some nice moments of reflection on the vanished Chicago and only a little of the “things were so much better then” nostalgia that threatens any project like this. I come away from this thinking it would be good to spend an afternoon with Wiedrich, who still seems sharp, but that the book itself doesn’t quite give a new look at the history he first helped uncover.


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