• Sue Kwong

This winter, the Reader has set a humble goal for itself: to determine the Greatest Chicago Book Ever Written. We chose 16 books that reflected the wide range of books that have come out of Chicago and the wide range of people who live here and assembled them into an NCAA-style bracket. Then we recruited a crack team of writers, editors, booksellers, and scholars as well as a few Reader staffers to judge each bout. The results of each contest will be published every Monday, along with an essay by each judge explaining his or her choice. The Reader reader who best predicts the judges’ rulings will win a trip to Mexico.

In this week’s contest, the second bout in round two, reviewer, bookseller, and former Reader managing editor Jerome Ludwig has the unenviable task of deciding whether Mike Royko’s Boss or Nelson Algren’s Chicago: City on the Make will be bounced from the tournament. To see the results of previous bouts, look here.

Royko versus Algren.

This is a tough bracket.

Boss is a meaty book. Meaty like a juicy, big-as-your-head steak. There’s a lot to chew on here, all seasoned with peppery Roykoisms.

Each chapter of Boss is introduced by a selection of Mayor Richard J. Daley’s testimony at the Chicago Seven trial, a little morsel to set the tone for what follows. And what follows is generally infuriating.

In Boss, Royko details Richard J.’s rise from political flunky and coattail rider to the most powerful mayor in the country. It’s a fascinating tale of politics, corruption, patronage, nepotism, cronyism, behind-the-scenes machinations, and dumb luck (more than one person in his way just happened to fortuitously drop dead).

It’s a well-known story by now, Richard J.’s reign. But Boss is worth reading to this day, not only for historical and journalistic purposes, but for the aforementioned notes of Royko pepper.

On the occasion of Daley attending a wake: “His arrival is as big an event as the other fellow’s departure.”

On the division of neighborhoods by ethnicity: “But you could always tell, even with your eyes closed, which state you were in by the odors of the food stores and the open kitchen windows, the sound of the foreign or familiar language, and by whether a stranger hit you in the head with a rock.”

And along the way: race riots, police riots, the 1968 Democratic convention, the murder of Black Panthers Fred Hampton and Mark Clark . . . Oh yeah, Chicago had it so good under Daley. It was a city on the make, for sure.

Which brings us to Algren and Chicago: City on the Make.

If Boss is a big, meaty steak, Algren’s slimmer City on the Make is more of an artfully arranged breakfast of bacon and eggs, to be savored and appreciated and lingered over, maybe with a side of sausage links, maybe with a beer back. (Eh, most likely with a beer back.) Boss is journalistic; City on the Make is poetic.

You’ve heard this before, Algren writing of the city: “Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.”

But this follows soon after: “It isn’t hard to love a town for its greater and its lesser towers, its pleasant parks or its flashing ballet. Or for its broad and bending boulevards, where the continuous headlights follow, one dark driver after the next, one swift car after another, all night, all night and all night. But you never truly love it till you can love its alleys too.”

Royko’s Boss names names; Algren writes of the nameless: “crippled newsies,” “the pinboys,” the “backslum loudmouth,” the “whiskey-heads and hopheads, old cokey-joes and musclemen,” etc.

The books are excellent to read in tandem, by the way. The same city, the same winners, the same losers—just rendered differently.

Both books are great. I highly recommend them. An airtight argument can be made for either to advance to the next round. I can hardly stand to choose one over the other. Steak vs. bacon and eggs (and beer). Journalism vs. poetry. It depends on your appetite.

So, let’s call it a tie . . .

So, how to break the tie.

My mother read Royko’s column at the breakfast table every weekday. She loved Royko. Point for Royko.

The Studs Terkel factor: Studs blurbed Boss (“Stunning, astonishing, myth-shattering”). But Studs wrote the intro to City on the Make. Point for Algren.

This could go on for a while. Time to think outside the box. Outside the books.

As it happens, there exist a couple volumes of love letters involving both writers.

One is Royko in Love: Mike’s Letters to Carol. Michael Miner called it “one long promise from Mike Royko to Carol Duckman that he will love her the rest of his life.”

The other is Simone de Beauvoir’s A Transatlantic Love Affair: Letters to Nelson Algren (aka Beloved Chicago Man: Letters to Nelson Algren, 1947-1964).

(On a side note, neither Carol’s letters to Mike nor Nelson’s letters to Simone have survived.)

I haven’t read Mike’s letters to Carol, but I have read Simone’s letters to Nelson. And they are amazing. Passionate. Charming. Funny. Erudite. Political. Sexy. And English wasn’t even her strong suit.

Here’s a sampling of her salutations to the Chicago writer, in chronological order. I think you’ll get the drift of how their relationship grew:

Dear Nelson Algren

Dear friend

My precious, beloved Chicago man

Nelson, mon cher amour

Dearest darling you

Dearest naughty you

Sweetest faraway you

My own beast

My darling own beast

My own beastish beast

Sweetest you, sweetest of all monsters in the world

My nice faraway wrapped in the blizzard you

Dearest sitting and brooding local beast

My poor dearest American dilemma

Dearest Division Street Dostoyevsky

Dearest man with the golden arm

My man with the golden brain

On the strength of that, I give the edge to the man with the golden brain. Chicago: City on the Make advances. Just by a nose. (Not even by the length of Royko’s prominent beak. A much shorter nose than that: the nose of a Frenchwoman.)

P.S. On the acknowledgments page of Boss, among the “many knowledgeable Chicagoans” that Royko thanks: Nelson Algren.

You readers rightly predicted that Judge Ludwig would have a hard time choosing between these two heavyweights. Boss edged City on the Make by a mere two votes. If this were a mayoral election, we’d have them square off again in April. Instead, City on the Make advances alone. Voting for round three begins February 10.

  • Sue Kwong